On Dating

On goal-oriented dating

I’m in my last year at a good university, enjoying life and getting excited about heading out into the professional world. My biggest insecurity is that I’ve never had a relationship that’s lasted longer than a month. In high school, I was a late bloomer in the dating scene and never even hooked up with someone until the summer before Senior year. Most of my “relationships” (if you want to call them that) have been with girls whose company I enjoy but the chemistry just never seems right. I just can’t seem to find the right girl that I’m both attracted to and has a personality that matches mine. I’m an attractive, social guy, and I don’t put out the desperate vibe – I feel like it’s just circumstance that I haven’t found anyone. But it’s gotten to the point that it really bothers me. I feel like college is a time when I am surrounded by people my own age and of similar intelligence – if I graduate without having had a single meaningful relationship, I’m going to be pretty unhappy. Am I being overly analytical? Should I be less picky?

You don’t need to be less picky. You need to be in less of a hurry. Your problem isn’t that you’re being overly analytical. It’s that you’ve got a ridiculous master plan for your life that includes charts and graphs and a timetable.

I know your type. There’s a voice in the back of your head constantly reminding you that you’re supposed to be married with 2.5 kids and a golden retriever by the time you’re in your mid-thirties. This voice says you’re supposed to date around for a few years before you find the perfect girl and settle down. It says you’re supposed to be in a stable, long-term relationship for a couple years before you get married, and it says you’re supposed to be married for a little while before you start having kids.

This voice in the back of your head (which sounds suspiciously like your mother) has already done the math, and quite frankly, it’s a little disappointed that you didn’t find your future wife during college. Well, guess what, skipper? You need to tell that voice to shut the fuck up, or you’re gonna end up leading a miserable life.

You’re wrong about what will make you unhappy. It isn’t the fact that you might graduate without having had a single meaningful relationship. It’s that you’re blind to the fact that regardless how long they’ve lasted, all of your relationships have been meaningful.

Every random hookup, every super-cool chick you weren’t really attracted to, every potential girlfriend that fizzled after the third date – all of them count as meaningful relationships, especially during your college years.

Your single biggest mistake is that you think you have to find the right girl and spend a predetermined amount of time in a relationship before it counts as meaningful. (I’m guessing with you, it’s probably three months.)

Do yourself a huge favor and throw the timetable and your ‘right girl’ checklist out the window. Stop being so damned goal-oriented with your dating. Come on, man. You’re in your early twenties. Smell some fucking roses already.

On nice guy syndrome

I’m a 21 year old guy with one more semester of college left. If there was a textbook of “nice slightly geeky guy,” it’d have my picture there. I’m not fat, I’m not pimply, but I’m not cut or super-hot either… just a slightly above-average looking guy who knows how to treat a girl.

All of that introduces my question: why is it that I always get thrown into the friend zone? To clarify, I get put into the “gay best friend” zone. I’m straight as the day is long, but I’m the one who gets to hear about new shoes, shopping, cute boys, shitty boys, assholes who stood them up… you get the drift.

Is it because I listen too much? Am I too nice? Should I not offer a shoulder to cry on, tell her the shoes are cute (when they are), or that the dude she’s dating is a douche who’s probably fucking someone else too?

Can you help me? I’m asking because there’s a gorgeous, intelligent girl I’d usually say is out of my league that has expressed lots of interest, and I don’t want her to turn me into another “gay best friend” style friend, where I get to hear about her day, her shoes, and her boy problems.

Ugh. Nothing rolls my eyes into the back of my head faster than a ‘nice guy’ who whines about being in the friend zone, and quite frankly, if it weren’t my job to try and smack some sense into you, I’d tell you to go fuck yourself for the ignorant ‘gay best friend’ remarks. (Not cool, dude.)

Let’s be clear, you are not a nice guy. You are actually a magnificent douchebag with a raging case of Nice Guy Syndrome. (Yep, it’s a thing. Look it up.)

While we’re at it, let’s be clear about something else. You don’t know how to treat a girl. You say you do, but you don’t have the slightest fucking clue. If you really knew how to treat a girl, you wouldn’t bitch about listening too much, and you wouldn’t act like a shoulder to cry on is only something to offer if it’s in furtherance of getting you laid.

That kind of thinking is glaring evidence of the underlying issue with guys like you. You don’t actually respect women. You pretend as if you do, and you may even believe that you do, but it’s not real.

It’s outrageous and downright insulting that you think a girl has the ability to turn you into a ‘gay best friend’. You’re doing that to yourself, because you aren’t really being a friend in the first place. You’re just acting like one with the ridiculous expectation that platonic behavior on your part might somehow transmogrify into romantic behavior on her part.

Sorry, but it doesn’t work that way. Platonic relationships are different to romantic ones. They begin differently, they progress differently, and they sure as hell end differently. You’d better cozy up to that fact pretty quick, because you simply cannot continue to behave like this with the new relationship. If you want a romantic relationship, you have to be emotionally honest from the get-go.

You have to put yourself out there, and if she rejects you as a potential romantic partner, you have to move on without thinking platonic behavior will eventually entitle you to something romantic.

On being easy

Some advice: if you fuck on the first-date, he probably won’t come back for a second. If the sex was hot and he does come back enjoy becoming fuck-buddies, because by fucking on the first-date, you’ve essentially told him by your actions: “I’m easy and definitely not the type of girl you’ll be wanting to take-home or marry, because anyone who I find attractive and who picks up the bill, I’ll let fuck me.”

I can appreciate the brass balls it takes to offer someone like me unsolicited advice, but honey, not only are you in way over your head, you’re also wrong about life. I fuck who I fuck when I fuck because I wanna fuck, and I don’t give a flying fuck whether the people I fuck think I’m the marrying type. That doesn’t make me easy. That makes me hard.

I am the one in command of my own sexual virtue. I am the one who defines that virtue. No one else gets a say in it – not you, not the world, and certainly not some guy I allowed the privilege of fucking me on the first date.

Everything you believe to be true about sexual virtue is a tragic lie instilled in you by a misogynistic, patriarchal culture that is fundamentally terrified of female sexuality, and that bullshit needs to be systematically unlearned. I’d feel sorry for you if you weren’t making yourself part of the problem by spreading around this kind of ignorant, regressive poison.

On doing what needs to be done

My friend-with-benefits sent me a text saying “You need to back away from me until you can control and handle your emotions. You’re being clingy, obnoxiously attached, and irrationally upset for no goddamn reason. Until then, please do something constructive instead of sending me a text.” He just sent this straight out of the blue and I’m about 5 seconds from kicking his ass to the curb. I can’t keep giving him second chances. I need advice. Help. Anything.

You can only give somebody one second chance. After that, ‘giving him second chances’ is just code for putting up with more of his bullshit.

And let’s be clear, he didn’t send that text straight out of the blue. You may not want to admit it, but you know damn well why he thinks you’re being clingy, obnoxiously attached, and irrationally upset for no goddamn reason.

I’m not saying he’s right. I’m just saying quit acting all surprised. Even if he is right, he’s still behaving like a gigantic asshole, and you shouldn’t tolerate a lack of respect like that from a friend, with or without benefits. It doesn’t sound like a healthy relationship, so you should probably take your five seconds and then go ahead and kick his ass to the curb.

Now, here’s the real question. Can you do what needs to be done, or are you just in this for the drama?

On flirting

How should a male feminist flirt? (I get the impression that a little guide to this might help ease the symptoms of Nice Guy Syndrome sufferers…)

Oh my god, no. It is definitionally impossible to be a male feminist who suffers from Nice Guy Syndrome. The two couldn’t be more mutually exclusive. If you really are a male feminist, whatever social awkwardness you might be suffering should never be confused with something so gross as Nice Guy Syndrome.

What bugs me even more about this question is the assumption that courtship rituals are somehow different for male feminists than they are for other dudes. You’re not special because you identify as a male feminist. In fact, that’s not a label you get to claim for yourself, especially in this context. I’m sorry, but your behavior has to speak for itself.

How you should flirt as a male feminist is no different than how any dude should flirt, and quite frankly, there’s nothing I can tell you about flirting that shouldn’t be patently obvious to someone who claims to be a male feminist. But hey, since you asked, here’s my two cents:

First and foremost, be situationally aware. Ninety percent of the awkward moments in the known universe could be avoided if guys would just pay attention to their surroundings before hitting on a girl.

Is it an appropriate time and place for you to flirt? Do you have any indication that your advances might be welcome? Is there anyone who might be made to feel uncomfortable if you started flirting? If you don’t have clear and positive answers to all of these questions, then any move you make will be a one-way ticket to awkward town.

If you do have a handle on the situation, then it really just comes down to being respectful and not saying stupid shit. The goal is merely to telegraph a little bit of romantic intent through non-verbal cues.

Please note, I said romantic intent, not sexual intent. Leave your dick out of the equation. Communicating the idea that you find a woman attractive is not the same thing as communicating the idea that you want to fuck. If you fail to comprehend this simple distinction, then I assure you, you are not a male feminist, and for the sake of all womankind, you should probably never go out in public again.

Good luck with the flirting. Oh, and did I mention? Don’t say stupid shit.

On a dick tease

What was supposed to be a no biggie fling has turned into a brain exploding headfuck with a guy who has suddenly decided he doesn’t want to sleep with me because he “respects me as a human-being” and even though he finds me “extremely sexually attractive” doesn’t want to use me like a “toy” and is afraid sex will lead to “feelings”.

The misogyny embedded in his dick-teasing explanations for not wanting to fuck make me want to put my head through a wall. Last time I was single, this city was a casual sex fest. I haven’t yet encountered this shit and I’m really confused.

I’m pretty butthurt I didn’t get laid cos, apparently, I’m a “woman” and I have “feelings” and those “feelings” are activated through my vagina. How should I process this stupid shit?

He just didn’t want to fuck you. It happens. Get over it.

It’s okay, though. I know his type. The sex would have been terrible, and he’d have been calling you a cab while you were still wiping his cum off your tits.

Of course, that’s what he was trying to tell you with all that coded ‘nice guy’ bullshit. You just have to know how to read between the lines. When this guy said he’s afraid sex would lead to ‘feelings’, what he meant is that he’s afraid sex would lead to ‘you being needy’.

And he doesn’t find you ‘extremely sexually attractive’ any more than he ‘respects you as a human being’. That’s just him being patronizing. After all, for him to think that casual sex would be ‘using you like a toy’ pretty much sums up his internalized opinion of women as sex objects.

I get that rejection sucks, but not getting laid by an emotionally crippled douchebag ain’t the worst thing that’ll happen to you this week. Hard dick is good to find, but good dick is harder to find than you think. Keep looking. You’ll get some soon enough.

On the harm in flirtation

does instant messaging with a man twice my age who’s married to a wife i really admire and who just had an adorable baby make me feel nervous and guilty because i know he and i mutually think one another are awesome and even though i would never never never do anything, this is the way people who do things start out, or is it because i’d just like to tell myself i wouldn’t but I really would?

You’d never never do anything? Bullshit. If the two of you have to hide the instant messages from the wife, then you’ve already crossed the line.

A little flirtation can be harmless. Hell, a lot of flirtation can be harmless, but if it becomes a thing she would be hurt to discover, then you shouldn’t be doing it. The betrayal is in the secret, not the act itself.

Of course, you already know that, which is why you feel nervous and guilty.

How do I date my best friend?

Carefully, only once, and with the full knowledge that it could easily destroy the relationship.

What does my poor choice in men tell me about my self-esteem?

I dunno. Choices only become poor with hindsight. You chose those men for a reason, and those reasons satisfied a short-term emotional or physical need at the expense of your long-term happiness. What are those needs? Are they linked to your self-esteem? Are there patterns of behavior that you can identify and learn from and not repeat? You’re the one who has to answer this question for yourself. I can’t do the work for you.

I’ve been out with a new guy on about 4 dates. He recently told me that he has never been in a relationship. We’re both 26. Red flag?

Depends on what he considers a relationship. If it means he’s never been in love, it’s not a red flag. If it means he’s never been exclusive, it’s a yellow flag. If it means he’s never gone on a 3rd date, it’s a red flag.

Casual guy told me I was too smart for him/he couldn’t keep up. Then we fucked one last time and he ghosted. It’s just an excuse cause he’s not into it, right? What the fuck

The whole ‘he’s just not that into you’ thing implies that it actually had something to do with you in the first place. In a casual world full of narcissists, y’all need to start getting used to the fact that it wasn’t ever about you to begin with.

Why does it bug me so much when guys call me a tease?

Because not only are they implying that you use your sexuality as currency, they’re also suggesting that they’re owed some of it.

What does it mean when a guy doesn’t want to get into a relationship with you because he doesn’t want to disappoint you?

It means he doesn’t want to be in a relationship with you.

I have had numerous men tell me in so many words that I’m unlovable. It’s clear they think I’m smart, fun, pretty, etc, but I don’t evoke an emotional response in them. How do I interpret this? How do I not let it (continue to) ruin my self-esteem?

Nope, nope, nope. Unlovable is your word, not theirs. You are not unloveable. You simply have a pattern of picking emotionally unavailable men. Pick better men, and while you’re at it, stop letting their faults inform your self-image.

On rejecting an older man

There’s a man in my life that I’ve known for almost six years now & our relationship is complicated. He’s older than me by 20 years exactly (I’m in my 20’s), & until recently we were just good friends. Two years ago he said he was in love with me & has told me so several times since, as well as buying me various expensive gifts. We’ve never been sexually involved & we live on separate sides of the country, so we don’t see each other more than once a year. I do care about him as a friend & a person but I’m not in love with him & don’t have any desire to be with him. I’ve told him I don’t love him but he says that doesn’t matter & he loves me anyway. At this point I don’t know what to say, & I feel guilty that I don’t return his feelings. Any advice?

Both his age and the fact that you feel guilty for not returning his feelings are evidence that he is emotionally manipulating you. You need to take a step back and recognize that you are being inappropriately pressured.

You are in no way obligated to return his feelings. If you’ve made it clear that you don’t have any desire to be with him and he says it doesn’t matter, that means he is showing you disrespect. Fuck that shit.

Stop allowing him to give you romantic attention. Definitely stop accepting gifts from him, and if necessary, return the gifts that he has already given you. I know it’s nice to get gifts and attention, but you can’t let that shit happen if you just want to be friends.

Be kind, but be firm. Let him know that you are not romantically available for reasons that should be plainly obvious. Your age, your distance and your unrequited feelings make a relationship impossible, and if he can’t move on, then you may have to sever the friendship.

(Oh, and while you’re at it, stop using a damned ampersand when it’s just as easy to type the word ‘and’. Don’t be fucking lazy about the details.)

On dudes losing interest

I can’t detach emotions from sex. I’m single and dating but whenever I try to hold off on the sex until I’m ready, dudes get impatient and lose interest. When I’ve gone ahead with the sex on the first few dates, I feel gross and used. I try to date all different kinds of men and I like to think I can weed out the douchebags but apparently something is amiss. What can I do?

Keep doing what you’re doing. Nothing is amiss. You’re on one end of a spectrum where dudes get impatient and then lose interest. Women on the other end of that spectrum fret just as much as you do, because they have experiences where dudes get laid right away and then lose interest. Either way, dudes lose interest, and women find every way to blame themselves without recognizing the broader pattern.

Dudes are gonna lose interest. It’s what dudes do. Occasionally you’ll find one who’s legitimately looking for a long-term relationship, and if it’s for healthy reasons and you two have chemistry, you might become a thing for a while. Whether that happens or not has nothing to do with your ability to detach emotions from sex. Don’t scapegoat that aspect of your personality. It may be the reason dudes get impatient, but it’s certainly not to blame for why dudes lose interest. That’s on them, not you.

If sex before you’re ready makes you feel gross and used, don’t do it. If a guy you’re dating gets impatient, tough shit. If he loses interest, fine. Good riddance. Dating should never be about keeping someone’s interest at the expense of your own emotional well-being.

On a selfish cheating asshole

I drunk fucked a guy I work with. I’m 24 and he’s in his late 30’s. He’s married and has a kid, I have a boyfriend I moved states for. Its an all around bad situation. The sex was amazing, but it was just sex. Theres no chemistry on either side that is anything close to how it is with each of our SO’s. But I’m worried its going to happen again … The sex was so good. I don’t want to lose everything but I am young and I want to have good sex while I can. Am I going to hell?

There is no hell, you selfish cheating asshole. What you did is wrong. Don’t fuck your married coworker ever again, and don’t use alcohol or your youth as an excuse for your shitty behavior. If you need a more adventurous sex life, then either be honest with your boyfriend and open up your relationship, or break up with him and start fucking some non-married non-coworkers.

Have some fucking integrity, bitch.

Is it morally reprehensible to seek & be flattered by male attention even though you don’t have the slightest interest?

Attention seeking can be a bit shallow, but it’s not morally reprehensible unless you’re also engaging in deception or dishonesty.

I fucked a guy with a wife and baby on the way. He just got married but he’s been living with the girl for more than 5 years. I don’t even know if I like him. It’s just I want – SO BADLY – for him to like me. It’s the lowest I have ever GONE. And I need some slaps in my face to snap out of it.

You know what you did was wrong, so let’s set aside your shitty behavior for a moment and help you recognize a deeper truth: the worst thing about you is that you believe you need to fuck a guy in order to get him to like you.

Your thoughts on a guy who counts his sexual partners and boasts with his number?

Don’t fuck him. He’s terrible in bed.

What exactly characterizes the border between pursuing a love interest and being creepy/obsessive?

Putting your wishes ahead of theirs.

Why am I attracted to arrogant dudes?

Ask your dad.

Nothing makes me feel smaller or uglier or more like a piece of shit than someone I care about showing romantic interest in me, and I don’t know why. I wish I could get people to stop.

The reason it makes you feel small and ugly is because you consider romantic interest to be an unsolicited sexualization of a platonic relationship. It’s a shift in how you think a person values you, one that degrades your own self-worth. It doesn’t have to, though. The trick is in realizing and fully accepting that you’re not doing anything wrong. You’re not the one betraying the fundamental nature of the relationship. They are.

If someone openly says that they are not a good person, and also includes that they don’t know what it means to love someone, would it be stupid to date them? Is it stupid to even ask?

They are either telling the truth, and you shouldn’t date them, or they are playing games with you, and you shouldn’t date them.

On not getting hit on

Why won’t guys look at me? I’m 30, pretty, smart, well-educated and have a good career. I like to think I’m a strong woman (or at least appear to be strong, since I’m whining here). Yet when I go out with friends, all of whom are in relationships, guys hit on my friends, never on me. It’s like I don’t exist. True, I’m not very good at hitting on guys, but my friends get hit on without doing anything. Damn, sending this question feels weird.

Either you’re wrong about being pretty, or you’re wrong that guys never hit on you. Take your pick. It’s one or the other.

If you’re willing to jump right in and call yourself pretty, I’m willing to give you the benefit of the doubt, which means that unless you’re an insufferable bore or a big pile of awkward, you’re probably just clueless when it comes to being hit on.

Odds are, you have a selective memory. You remember all the guys who hit on your friends, and you remember all the guys who didn’t hit on you when you wanted them to, but you don’t remember any of the poor bastards who tried hitting on you when you weren’t interested.

Of course, pointing this out doesn’t solve the real problem, which is that you secretly think all your friends are much more attractive than you. It doesn’t matter whether this is objectively true. What matters is that you believe it to be true.

Yes, that’s really the problem. I didn’t need to know that all your friends are in relationships, but you thought it was important enough to tell me. It bugs you. That’s the tip of your iceberg of resentment.

This entire question is a head-fake towards male attention when at your core you have issues with female competition among your friends. You start out with, ‘Why won’t guys look at me?’ when what you’re really asking is, ‘Why are guys looking at them?’

That kind of indignation is poisonous to female friendship, especially when you don’t recognize that it’s there. You need to acknowledge some of your underlying feelings about your friends, and deal with them before your negativity starts to fester.

On a lazy idiot

ive been dating this girl for over a year now and have found over time that she has slept with way more dudes than i thought. she also took my virginity. i cant help but feel like this imbalance is eating away at me. got any words of advice?

I’ve got plenty of words of advice, but you’re an idiot and nothing I say will stop your male ego from eventually destroying your relationship so that you can add a few notches to your bedpost. That’s fine, though. She can do better, and you need some time to fuck around and figure out what’s important.

In the meantime, start using capital letters. Your shit is lazy.

On boundaries

There’s a woman at my office (the receptionist), who’s really attractive (duh, receptionist). In my professional capacity I don’t have much interaction with her but I’d really like to find a way to create some without being another creepy dude making contrived moves(I know that’s what I’m doing, hopefully with less creep). Who knows if we’ll even click… this isn’t about trying to fit where I can’t, but I’d like to give it a legitimate try without boning my chances by being a typically awkward guy.

Pen, company ink. I get it. I’m adult enough to not let that kind of shit get to me if it doesn’t work. Aside from not dating someone from work, what should I do?

Aside from not dating your receptionist, you should also not hit on your bartender, you should not ask out your waitress, you should not proposition your stripper, and you should not kiss your prostitute on the lips without permission.

Listen, jackass, this isn’t about being adult enough to not let shit get to you if it doesn’t work. It’s about being adult enough to respect the boundaries of professional relationships.

On not seeing the point

He’s trying to get to know me, but I just want to fuck. Why do guys insist on going through this phase? I just don’t see a point unless you’re looking for something serious.

Oh, I don’t know. Maybe it’s because you’re a beautiful and interesting human being worth knowing beyond your vagina who somehow doesn’t quite grasp that the delicious complexity of interpersonal relationships can’t be reduced to a binary state of ‘something serious’ or ‘I just don’t see the point’.

Or maybe he’s just a dildo with a dude on the end of it.

Which do you think it is?

On going out with a bang

I’ve been dating this guy for the last week, but right now I’m just not emotionally available. I feel like I should break things off, but I wanna have sex with him first. Is that a really dick thing to do? I feel like it is… Should I do it anyway?

Shit, it’s only been a week. Just be honest. Make plans to see him one more time. Look him in the eye and say, ‘I’m not emotionally available right now and I don’t think I can keep seeing you, but I’d really like to have sex with you tonight.’

It’s a win-win. Not only are you shooting him straight, but I guarantee he’ll bring his hair-pulling, ass-smacking A-game just to see if he can change your mind.

At the end of the night, just give him a kiss goodbye.

Good times.

How do you say no to someone who continuously asks you out and refuses to stop, even upon request?

Tell the creep to fuck off. Be rude. Be loud. Embarrass him for not respecting you, and when he acts all butthurt and calls you a bitch, don’t feel the least bit bad about it.

Why am I attracted to guys who always have one foot out the door?

So that you can experience all of the emotional drama without taking any of the emotional risk.

Any tips on how to tell if a married man is lying about being in an open relationship, without asking his wife?

Look him in the eye and say, ‘Tell me about how you and your wife decided to open up your marriage.’ You’ll immediately know if he’s full of shit.

My fuck buddy wants a relationship. What’s the least awkward way to tell him that I’m not looking for a commitment?

Use whatever words you’d like, but the least awkward way is to immediately stop fucking him.

Is it okay to talk to and fuck someone who is ugly when you are not?

I dunno, you sound pretty ugly to me.

I hate every man who starts to like me after I’ve slept with them. How do I stop?

It’s not hate. It’s a reflection of your own self-loathing that you use as a clumsy defense mechanism to protect yourself from vulnerability.

I am relatively sought-after, but my high standards have made me lonely. How do I fix this?

Your high standards aren’t the problem. It’s your unreasonable expectations that are keeping you lonely. There’s a difference.

Is sleeping with your teacher morally wrong, even if their not married?

Is it your English teacher? Because you need to learn the difference between ‘their’ and ‘they’re’.

On making a move

So I’ve got a mad crush on this girl who lives on my hall. We’ve been hanging out and stuff, probably to the point where she thinks I’m just her friend. And I’m bad at picking up signals, but I get the feeling that there could be something here. (This is coming from a guy with zero, zero, zero experience. But I’ve already complained about that for years. It’s time to make a change.)

We went to Harry Potter last night and blazed together. Unfortunently we were with a bigger group as well of mostly her friends so I couldn’t try anything. That sounds stupid to me because I have no idea what I’d ‘try’.

So what’s the best option for me right now as far as making the next move? Remember…I am a total loser who hasn’t had any experience with girls and somehow I made it to college a virgin, because I’m that cool. I’m not solely out for sex, though; I like her.

Dude. You’re fucking precious. I just wanna tussle your hair and pinch your cheeks and shit.

Listen up, this isn’t about ‘trying’ anything. Don’t make this about your virginity. Nobody gives a fuck about your lack of experience except for you, and trust me, you’re surrounded by virgins.

I can’t tell you how to make a move here, kid. That shit is on you. Accept your vulnerability, accept the possibility of rejection, and then just be brave and fucking do it. Making a move is an organic, in-the-moment kinda thing, but I will say this, if you think there’s a romantic spark between you and this girl, you’re the one who’s gonna have to acknowledge it.

Be sweet about it. Be honest. Use whatever words or actions that come to you naturally in that moment of bravery, but the gist of it doesn’t have to be any more complicated than, ‘Hey, I like you, and I think you like me too. Here we go!’

Do it with a kiss. Do it with your own words. However you do it, get it fucking done. Don’t worry about what happens next. For better or worse, the heat of that moment will become self-sustaining once you get it started, unless of course you fuck it up by overthinking shit.

Whatever. You’re gonna do what you’re gonna do.

Tell you what, though, you’re not a total loser. That much is for sure. You just need to get out of your own head. Quit complaining, and savor the experience you’re about to have.

Learning this shit is ten times more exciting than already knowing how to do it.

Fucking enjoy yourself.

On hesitation

Whenever I think I like someone, I always put up walls. Half the time I’m scared to commit because I don’t think people will be able to handle me. I always end up convincing myself I don’t like them, but I don’t like seeing people get hurt…What’s your opinion on this?

Oh please. You’re the girl standing in the freezer section of the grocery store staring at the ice cream like her head is about to explode.

It’s fucking ice cream, bitch. It’s creamy and delicious. You know you want some. Quit making lame excuses for yourself and pick a damned flavor already.

On a complicated dilemma

I have a dilemma and i need your advice. my best friend’s roommate and i are totally into each other, and the best friend is pissed and is begging me not to hook up with her. In addition, the roommate is currently in a relationship with this really nice guy who’s pretty chill. I don’t want to be a relationship breaker, nor do I want to fuck up my friendship with my best friend. What would you do? Hook up with the roommate asap, wait for the roommates current relationship to end, or not hookup with the roommate at all?

You seem to have way more experience with complicated relationships than I, hence why I ask you.

Here’s what you should do. Go get a dictionary. Look up the words ‘dilemma’ and ‘complicated’. Note that neither of them should be used to describe what’s going on with your pathetic excuse for a lack of self-control.

You’re a piece of shit for even considering this. Seriously, dude. You’re willing to drop a live grenade of hot messy drama into the middle of your best friend’s home so your dick can get wet for ten, fifteen minutes tops? Fuck you.

This is only a dilemma if you’re an emotionally crippled tool.

On sixteen

I’m sixteen and have never had a real relationship, just a bunch of mild drunken hook-ups. I don’t want to put time and effort into someone I’m not crazy about, but I’m afraid that when I actually have relationships, I’m always going to be the person who likes the other slightly more. Also, I have crushes on people I don’t know very well, so I can construct their personality into something I like better. And then I always find out that they’re assholes. Fix me?

You’re not broken. You’re sixteen.

All that shit you’re feeling is right on schedule, and the fact that you’re self-aware about it means you’re ahead of the game.

Don’t worry. One day, you’ll be able to spot assholes before you crush on them.

In the meantime, try not to think in terms of relationships. Just enjoy the company of interesting and respectful boys and/or girls.

On all there is to say

I’m 19 and i’m seeing this guy, but all we do is fuck. We’ve been dating for about a month and he knows nothing about me. Whenever we hang out all we do is have sex and then he sort of ignores me until I have to leave and then begs me to stay. The fucked up part is that he told me that he loved me about 3 weeks into the relationship (I don’t believe him). What’s this guys deal?

He’s an emotionally crippled piece of meat. Then again, so are you.

Stay off television and on birth control.

On secret affairs

Here’s my dilem. I’m having a secret affair with this guy. This certain guy has hooked up with my best friend a few months ago. He confessed to me that he actually likes me and could see us being more than fuck buddies. My best friend still isn’t over him even though they never actually dated (she gave him a bj and he was high and barely remembers it). I like him so much and really do want to be with him. But my best friend would be crushed if I dated him.

So, do I put my happiness in front of hers? or go the chicks before dicks route?

A secret affair? Don’t be so dramatic. This isn’t about love. Nobody’s married. You’re just sneaking some dick behind your best friend’s back after she tried calling dibs on it.

The whole thing is just a half-assed love triangle, the heightened circumstances of which are fooling you into thinking that this guy is more than a fuck buddy.

Don’t kid yourself. It’s a summer fling, one that’s going to ruin your relationship with your best friend when she finds out.

Yes. She will find out. It’s inevitable, and unless you’re the one who steps up and tells her what’s going on, she’ll never be able to trust you again.

This isn’t about your happiness. It’s about your integrity. Seriously, is your summertime fuck buddy worth your best friend’s trust?

Didn’t think so.

Why do I scare guys I like away, and attract the ones I don’t?

That’s just your confirmation bias talking.

How long is the “normal” amount of time to be single?

That’s good. The first step is putting it in quotes. The next step is realizing that there’s no such thing.

No matter what, whoever I date starts to look ugly to me after a while. Is this normal? How do I stop this from happening?

You’re confusing what they look like with what they are like. Even worse, you’re probably confusing what they are like with what you are like.

I want to be in love with someone who is kind, witty, and sexually attractive, and have them love me back. Why does it this seem so impossible?

Because you’re confusing kindness, wit and sexual attraction with long-term compatibility, and you’re confusing love with infatuation.

How do I stop feeling guilty about casual sex?

Stop believing casual sex is wrong.

Why am I so scared of committing to a nice, sweet guy who I regularly hang out and sleep with? What’s stopping me from making it official?

You still think you can do better.

I’m really great at finding hot, fun guys to fuck and having a hot night of sex. Not so great at turning it into either a regular fuck or a relationship. Any advice?

Yeah, stop trying to turn one-night stands into ongoing relationships. Going out for a hot night of sex and going out to meet guys are two completely different rituals with completely different codes of etiquette. Separate the two in your mind, and understand that you can’t do them both at the same time.

On dating in los angeles

I’m having trouble dating, specifically dating in Los Angeles, the land of superficiality. I’m a med student and I’ve been in Maxim, so I’m surrounded by nerds & get hit on by douchebags, neither of which I want to date. I keep getting wrapped up in men who are smart & successful but more interested in their jobs than me. What’s a girl to do to find an honest, hardworking family man in LaLaLand?

Honest, hardworking and a family man? This is Los Angeles, babe. Unless you wanna marry a Mexican immigrant, you can only pick two out of the three.

You’re a soon-to-be doctor, former model living on the west side of paradise. Don’t tempt the fates by also expecting Ward Cleaver to fall out of the sky. You’re asking for too much.

That’s not to say you don’t deserve happiness, but is this really an honest assessment of your criteria for a man? It all seems a bit simplistic – no nerds, no douchebags, smart and successful – I wouldn’t go so far as to call you superficial, but your lists of pre-requisites don’t seem to have any depth.

That’s not your fault. You’re young, and you’ve been too busy overachieving. You simply haven’t taken the time to do the kind of serious personal exploration necessary to figure out not just who you’re looking for, but why you’re looking in the first place.

Self-exploration is a tough thing to do, and I would imagine you come from a family that considers that sort of thing an indulgence. Still, and I’ve said it before, you need to look inside yourself instead of using an external set of guidelines handed down from your mother.

I’m not saying that you won’t find an honest, hardworking family man in Los Angeles, but you’re not going to find him with a grocery list. You’ll find him once you find yourself.

Good luck with the search, sweetheart.

On why you even bother

First, I’m going to say what everyone says: you’re great and I need an honest opinion, no holds barred. I was in a very long term relationship that ended a couple years ago. I’ve never been much of a dater – I’m one of those annoying people who just sort of fell into relationships when I was younger. However, I’ve been trying my best to get myself out there and meet guys, which seems so fucking impossible in New York (totally cliche, I know, but it’s true).

My real problem is that I’ve met a few guys that I’ve had a good few months with and then they start the disappearing act. You know, less frequent phone calls/texts, distancing themselves, and behaving badly. In some cases, they’ve ended it, in others I have, but always because of their actions. They’ve all been fairly normal, good guys. I’m a smart, fun, good-looking laid-back woman and I don’t see what the deal is.

For the sake of full disclosure (because I want the most honest opinion from you), I’ve slept with all of these guys within the first couple weeks (which I don’t think is a bad thing) and I tend to give people the benefit of the doubt. If a guy shows a serious interest in me and I like him, I don’t play hard-to-get. I’m usually very up-front and I don’t like game playing to get the “upper-hand.” Is this bad? Are these guys thinking I’m too available?

Am I just having a run of bad luck? Should I reevaluate my judgment on the men I’m choosing? Or should I just stop “giving away the milk for free?”

D. None of the above.

Your real problem is that you think you have a problem. You’re not experiencing bad luck, you don’t need to re-evaluate your judgment, and you’re not a fucking dairy cow.

Perhaps you should start questioning the underlying notion that you exist in a binary state of either couplehood or singlehood, and that the former is somehow superior to the latter.

After all, you’re the type who ‘just sort of falls into relationships’. It seems like you’re long past due for some introspection into why you even bother.

Why are you looking for a man? Do you need a man to feel safe? Happy? Fulfilled? Do you want a best friend? A partner in crime? Someone to pay the bills? Do you want kids? Come on, why are you even out there dating? Let me guess, because that’s just what you’re supposed to do.

You have no idea why you’re out there engaging in the courtship ritual. All you’ve got is some nebulous set of external relationship guidelines that you’ve pulled from popular culture and whatever your mother taught you. None of it is relevant to your core self, because you haven’t taken the time to reflect on what it is you want out of a relationship.

Now is as good a time as any to start figuring it out. The cool thing is, there’s no wrong answer here. Just be honest with yourself. What do you want?

Not to get all Cheshire Cat up in this bitch, but until you know where you want to go, you’re wasting your time wondering why you’re lost.

On being hard to get

Does playing hard-to-get (in order to get a guy) actually work?

Playing hard to get works on boys. Being hard to get works on men. In either case, don’t confuse hard with impossible.

On playing vs being

I’d appreciate it if you could elaborate on your perspective on playing hard to get vs being hard to get.

1) What practical difference is there between consciously holding back to stoke interest in a lover, and unconsciously holding back if they both serve the same ends?

2) Is playing/being hard to get even a legitimate tactic in romantic relationships? Isn’t appealing to someone’s desire for what they can’t have just a matter of ego rather than a substantial bond between two people built on mutual affinity?

3) you can’t be naturally hard to get AND consciously making sure you’re not too hard to get. You’ve contradicted yourself.

Everything about your question – all of it – falls squarely into the category of playing hard to get. You have yet to even grasp the concept of being hard to get.

Being hard to get isn’t a tactic. It has nothing to do with conscious or unconscious action. It just fucking is.

Stop thinking about it. Let it go. I know you want me to elaborate on the distinction, but until you start getting zen about this shit, it’s only going to frustrate you.

(Sometimes I wish I could end these things with the sound of a gong.)

Either way, just enjoy yourself. We’re lucky to live in an era where our livelihoods no longer depend on it.

On whether to text first

I hooked up with this guy I have liked for a while last friday. It is now Sunday and he has not texted me or tried to make any communication. I dont want him to think I like him even though i do.

should i wait for him to text me, or should i text him first?

Wait a few years until you mature into an emotionally honest woman who has enough self-respect not to play silly mind games with her cell phone, and then call him.

On bitterness

Best way to start dating again if still bitterly single from last meaningful relationship? And don’t say tequila, xanax or drunken sex.

How ’bout you lose the attitude?

It doesn’t matter how much of an asshole your ex was. You are responsible for your own emotional state. It’s your own fault if you’re bitter. Get over it.

If you’re packing all this emotional baggage, don’t even bother dating. It’s a waste of everyone’s time.

(Especially without tequila, Xanax or drunken sex.)

On just doing it

It has literally been over 12 months since I last had sex. Right now I’m contemplating ruining my friendships by having sex with them at a party and then having shit get awkward and whatever. So far as I can see it’s either that or continue my steady diet of abstinence. What should I do?

Is it really so hard to fuck a stranger? Quit acting like you’re married and go have some filthy, no-strings-attached, ‘What was your name, again?’ sex.

On poaching boyfriends

it seems i always have a thing for guys with other chicks, so my question is… is that bad? i can’t help it if i’m better looking then their girlfriends.

You can’t help being better looking, but you can help being a cunt. Don’t poach guys. It’s incredibly selfish and disrespectful. Do I need to remind you of the golden rule?

As hot as you think you are, there’s always somebody hotter. Would you want that bitch stealing your man?

On naughty pics

Here’s the deal. I met this guy not to long ago, over the internet. Blahblahblah to that, I have no problem with meeting people online. He is hot. Damn good looking And I usually go for the nerdy lanky boys. HOWEVER, this boy is gorgeous. On with the story. We talked for the first time last week on the phone, around tuesday or wednesday. We ended up having phone sex. I have NO idea how it even got to that point but it did. And I feel kinda weird about it because I do not do that with guys I have just started talking to. I like to keep some kind of respect for myself. He wants pictures of me sans clothing now. And I don’t know how to say no. Because let’s face it, I phone fucked the guy the first time talking to him. And after that, how do you say no to something as simple as pictures? Part of my thinks I wouldn’t mind, but part of me would like to save some kind of whatever dignity I may have left. I’m not quite sure what to do here.

Ah, the perils of 21st-century whoredom. Every last one of us has a few naughty pics floating out there in the digital ether, and nowadays the American teenage experience includes making your first sex tape before getting your driver’s license.

Billions of little red record buttons, so simple and ubiquitous, make it far too easy for boys to do what boys like to do – point and shoot. It desensitizes girls like yourself until you’re asking ridiculous questions like, ‘how do you say no to something as simple as pictures?’

Simple as pictures? Are you fucking kidding me? The legal and emotional consequences of turning a camera into a sex toy can be staggeringly complicated and more permanent than an STD.

If every iPhone shipped with anal beads instead of a camera, would you still be asking how to say no to something as simple as assplay?

You’re not sure what to do here because you seem to have devalued this part of your sexuality. Take a moment to reflect on the levels of trust and intimacy that are required to safely share naked photos with someone, and hopefully you’ll see that I’m not being facetious when I compare this to taking it up the ass.

Posing for pics can be incredibly hot, and shooting a wildly creative sex tape can be one of the most intimate things you do with your partner, but the decision to let anyone other than yourself control that content is a serious one.

Don’t kid yourself – the second you email naked pics to a phone-fuck buddy you met online less than a week ago, you’ve effectively posted those pics to every amateur porn site this side of Chatsworth.

Just tell the guy no. If he presses you, turn the tables on him – insist that he be the one to send raunchy pics. If he backs down, that’s the end of it.

If he follows through and sends you pics, tell him they aren’t raunchy enough and that he has to send more. Never promise to send any in return.

Demand that he send you dirtier and dirtier pics of himself until he either backs down, grosses you out, or gives you so much blackmail ammunition that there’s no harm in sending him a naked pic or two.

If you do ever decide to send him something, make sure he’s familiar with the doctrine of mutually assured embarrassment, and let him know that you’d go nuclear on his ass if he ever stepped out of line with your pics.

Be wild and have fun, but take this shit seriously.

On begging to differ

after reading all your posts, i realized that your typical answer to questions like “how do i tell someone i want to fuck them?” is plain and simple: just fuck them. i beg to differ. it is not that easy, especially for people who are a bit shy and conservative. i am one of those.

i want to fuck this college senior who is probably going to become my graduate student supervisor. i guess it would be an awkward thing to do since it is likely that i will work with this guy for 2 years or so…but that still does not deter me from wanting him. would you please be so kind to give me some steps before actually getting to the just fuck him step?

You beg to differ? Okay, fine. Keep doing whatever it is that you’re doing over and over again until you get a different result.

Also, keep missing the point. Keep letting life experiences pass you by. Keep making excuses for yourself, as if anyone gives a fuck that you’re shy and conservative.

If you want something, go get it. It’s not my job to give you strength. All I can do is point out that you’re an idiot if you think any of this shit is supposed to be easy.

How do I tell the girl I like that I’m interested in her without being awkward?

What’s your reason for telling her that you’re interested? Are you trying to date her? Fuck her? What are your intentions? Has she done anything to lead you to believe that she might have feelings for you too? Hell, is she even available? If you don’t have clear and immediate answers to all of these questions, there’s no hope of you not making it awkward.

If he’s under police investigation, he’s not at all boyfriend material, right?

If you have to ask this question, you’re not girlfriend material either.

Is there even a point in being in a romantic relationship between the ages of 18 to 21?

No, but that shouldn’t stop you from trying.

If a member of the opposite sex with whom you’re kind of friends asks you to go with him to a party, how can you know whether it’s a date or just two people attending a thing together because they’re kind of friends?

You do realize that you’re the one who gets to decide whether it’s a date, right? Yep, it’s completely up to you. (Relax, you can change your mind at any point throughout the evening.)

Why is it that when I’m dating a guy and I start showing more interest, they decide to disappear?

Because you don’t know the difference between showing interest and acting needy.

I’m 16, he’s 32. Legal where I live, but what are your thoughts?

One day, when you’re an actual adult, you’ll look back and realize how creepy it was for this dude to be having sex with you at 16.

Why when I think I like a guy do I always over analyze everything and then end up convincing myself that I don’t like him?

Because you don’t know yourself.

What’s the point in being hard to get? I don’t understand why it’s better than being easy. Why are harder to get people more deserving of respect?

The point isn’t to be hard to get. The point is to have high standards. You don’t understand because you don’t know the difference.

How can you tell if a guy likes you or if he just wants to fuck you?

Fuck him and then see if the phone rings.

Why would a guy that likes a girl ignore her over the phone, yet, clearly show that he’s head over heels in person?

Proximity to your pussy.

What’s your idea of a nice date night?

I prefer a genuine human connection followed by a healthy round of athletic sex. The rest is just window dressing.

Do I message a guy I found on OK Cupid when I joined just for laughs?

Sure. Then date, fall in love and get married. You know, just for laughs.

If I have to question whether he’s flirting or not, that means he’s not flirting, right?

Maybe, or it could just mean that one of you isn’t very good at it.

On a fucked-out cliché

There’s an asshole who doesn’t give a shit about me except for when we’re fucking, who I’m a little bit in love with. And then there’s the super nice guy who cares for me a lot, who I don’t feel anything for. Help me break out of this, Coquette.

I can’t do shit for you if these are the choices you bring me. Have some fucking self-respect and get rid of them both. Go be something other than a fucked-out cliché from the first act of every teen romantic comedy.

I mean, how hard is this? Once you’ve established that a guy is an asshole, stop fucking him and move on. Once you’ve established that you’re never gonna have feelings for a guy who’s romantically into you, set firm boundaries and don’t lead him on.

It’s bad enough to get either one of those things wrong, but to fuck up both at the same time and then bring it to me like it’s some kind of dichotomy? Honestly, get your shit together.

Don’t act like you’re trapped between anything here. You created this triangle, and you maintain it for a reason. You can walk away from it any time you want, but you get something out of it, so don’t come whining to me like it’s beyond your control.

This is some silly girl shit. Start acting like a woman and handle your fucking business.

On a contender

He’s a twenty-nine year old business owner with an enormous personality, well traveled, well read too. He’s incredibly nice but he’s ring leader of his wild circus of asshole friends.

I’m a twenty-three year old college dropout who’s back in school and just came through the tail end of my depression. I’m nice, I read, but am a very good (boring) girl who over thinks everything.

Please just tell me why it’s not going to work out before I fall tits up in love with him and his Ewan McGregor smile? I want to think that in time I can become a contender but that seems…unrealistic. Give it to me Coquette; hurt me so he can’t.

If you need me to point out a bunch of red flags and tell you why a particular relationship is doomed, I can do that, but that’s not what you’re really asking me. You just want me to say the magic words that will protect you from emotional vulnerability. Sorry, kiddo. There’s no such thing as magic.

Pain is inevitable. Relationships end. You are going to get hurt – maybe by this guy, but definitely by someone you care about, and there’s nothing you can do but accept it. If you live your life trying to avoid the possibility of future pain, you will end up a numb and timid creature without any stories worth telling.

Go ahead and fall tits up in love. Enjoy the feeling while it lasts. Just promise me you’ll quit thinking of yourself as a contender. That mindset is poisonous. You are worthy of him. Timing and circumstance might prevent you two from ending up in a relationship, but no matter what else happens, you are fucking worthy of him.

Confessing feelings to a guy. Good idea, bad idea?

Why are you confessing? What do you want to have happen? If you don’t have quick, rational answers to both questions, it’s a bad idea.

A one-night stand told me that I hide behind sarcasm. What does that say about me?

It says you let your one-night stands talk too much.

Why is it that the more guys hit on me, the less attractive I feel?

The more guys hit on you, the more conscious you become of your own physicality, and any positive male attention is far outweighed by your negative self-image.

Do you have to date tons of people before you know you’ve met the one?

You might have to date tons of people before you believe me, but there is no such thing as ‘the one’.

Why am I significantly more attracted to a guy knowing that he’s dated a fuck ton of hot chicks?

The same reason all your clothes have logos on them.

What do you say to a 26-year-old man who claims he might never be able to love again?

Say, ‘Lose my number, douchebag.’

Why do I always fall for guys that I barely know?

Because they’re a blank slate onto which you can project your fantasies.

I just want to date myself. Or at least someone very similar to me. I know it’s narcissistic, but is it wrong?

You only think you want to date yourself because you’re blind to the fact that you’re insufferable. (I promise, you wouldn’t put up with your own bullshit.) What you really want is to date someone who allows you to be yourself, despite the fact that you’re an asshole. Good luck.

What is a socially acceptable amount of people to sleep with before you get married?

You know what’s socially unacceptable? A preoccupation with how many sexual partners you or anyone else might have had.

If he’s the right guy but it’s the wrong time, is he the wrong guy?

He’s just a guy. The rest of it is all silly bullshit.

On a dirty whore

I’m a stripper, and I recently had a guy I’ve been sleeping with say I can come over after work, but only if I “shower off all the lapdances first.” I ride my bike a lot, sometimes to work, and I asked if it was about being sweaty (just to absolutely clarify) and he said that my sweat in his bed was encouraged, but that other men’s was not. What the fuck is his problem? That doesn’t even make sense. Why does me showering make him feel like somehow I didn’t just get done lap dancing for money?

Here’s some brutal truth. The guy you’ve been sleeping with is an ignorant misogynist who likes the idea of fucking a stripper, but doesn’t respect you or what you do for a living.

He asks you to take a shower because he secretly believes that you are an unclean woman. Not literally. Figuratively. He thinks you’re a dirty whore, and making you shower off after your job is his weirdo way of keeping you as his whore but getting rid of the dirty part. It’s outrageously disrespectful and more than just a little bit creepy.

Don’t put up with that kind of negative bullshit for one damn second. Call him out for being disrespectful, and if he gives you even the slightest bit of attitude, stop fucking him.

Say it with me now: good dick is never worth disrespect.

Good dick is never worth disrespect.

On proto-exclusivity

Found out my guy was sleeping with somebody else in the first few months we were dating. We weren’t calling it a relationship but it was exclusive (or so I thought). It was a year ago but I’ve only found out now. I’m devastated but I love him. Fight or flight?

If you weren’t even calling it a relationship yet, then it certainly wasn’t exclusive. Like you said, you just thought it was. That doesn’t mean it was acceptable behavior, but it does put it in a gray area. Here’s something to ask yourself: are you devastated that your boyfriend’s dick was entering another vagina contemporaneously with yours? Or are you devastated that your boyfriend may have engaged in willful deception early on in your relationship? One is a manifestation of petty jealousy, and you should just get over it in time. The other is a legitimate concern for what may have been a breach of integrity.

Ultimately, the question you need to answer is, do you trust your boyfriend now, within the context of your long-term relationship? If you think you can trust him, then stick around, be pissed for a little while, and then get over it. If you don’t think you can trust him, either find a way to repair that trust, or get the fuck out of the relationship.

Don’t make this about some girl your boyfriend used to fuck. Make it about your boyfriend’s integrity as it applies to your current relationship.

On bad dating advice

I’m no Mensa material, but I’m smart; not hot, but pretty and fit; well-educated (medicine graduate next year) and open-minded (thanks to traveling, mostly). I am also a yoga teacher and know 4 languages. Now, I’m no ideal and I’m not looking for an ideal man either; neither do I want a copy of myself. I just want somebody equal, a partner. My grandma has recently told me that, with my brains and confidence, I probably scare men away, and I should lower my expectations (and pretend to be less smart and versatile, basically). Is she right? Is it that men I’d consider equal are not interested in women like me because they can, as a rule, “do better”? Thanks.

Listen up, everyone: STOP LISTENING TO DATING ADVICE FROM YOUR GRANDPARENTS. Yes, they love you very much, and you love them too. No doubt they are adorable and wise and they have your best interests at heart, but that doesn’t mean they have the slightest clue what it’s like for those of us trying to find a life partner in this century.

Everything your grandmother told you was wrong. You don’t scare men away. You scare boys away (and that’s a good thing). If your expectations really are just to find an equal, then they are perfectly reasonable, and you shouldn’t lower them. Don’t pretend to be less smart or versatile. That’s insane. (Sure, playing dumb can come in handy every once in a while, but it’s not something you do with a man you respect.)

A man who is your equal by definition won’t be preoccupied with ‘doing better’ than you. I think you may be in a mindset where you believe there is a certain tier of men that are your equal, that it’s something you can identify based on a list of skills and accomplishments. That’s your real problem. You’re looking for a guy who looks good on paper.

I get that you’re a box checker. It’s obvious that’s your style, and there’s nothing wrong with that, but try not to define your equal by matching up résumés. That kind of dating profile mathematics is an exercise in pure frustration.

After he describes how I’m attractive and intelligent, what does it mean when he says “I’m not in a great place right now?”

It means, ‘Fuck off and die.’

I currently like a guy, but we’re both too shy to do anything about it. Are we doomed to just being friends?

Invite him over for movie night. Watch Paper Heart. It’s all about love and being doomed by shyness. It’s also incredibly boring, so after the first twenty minutes I suggest you go down on him.

Sometimes I think if I weren’t such an independent woman, maybe I’d have a boyfriend once in a while…

Sometimes I wish I could spray my inbox with weed killer designed specifically for shitty voiceover from Sex and the City.

Five days is too long to not call a girl after cuming on her face, right?

A classy guy like you? I doubt she’s counting.

I don’t want to date him, but I don’t want him to date anyone else. Thoughts?

Um, sucks to be you? Did you remember to take your pills? Put down the knife? I dunno, take your pick.

What’s a classy way of rejecting guys that try to pick you up at a bar?

Six little words. ‘I’m flattered, but I’m not available.’

So, oh wise one, how would YOU get a boyfriend?

First know why, then the how will follow.

How do you tell a flirt from one who actually likes you?

If she licks your balls, she actually likes you.

Should I call him back?

Do you have anything to say?

When’s the best time to make a move?

The second before you start wondering whether you should.

On paying attention

I assume you are a beautiful girl, and obviously confident and full of spunk (spunk?). Are you flattered, interested, or just pissed and annoyed if a guy in a coffee shop / restaurant / bar asks you out? Should I say something when I see a girl I’m attracted to in these situations, or just keep my fucking mouth shut?

Dude. You should be able to tell whether I’m flattered, interested, or just pissed off and annoyed within a fucking microsecond of approaching me.

Women are walking symphonies of non-verbal cues. Eye contact. Body language. Facial expressions and gestures. Are you fucking kidding me? It’s not even something we can consciously control. We drop a million hints a minute whether we like it or not, but most of the time you idiots are too blunted by alcohol or blind lust to notice.

If you walk up to me in a public setting, you’ll get a flood of information about what I think of you long before we exchange a greeting. Just pay attention, man.

Was that an extra half-second of eye contact or did I just think your hair looked ridiculous? Am I wondering if you’re going to talk to me, or am I wondering if the guy next to you went to high school with me?

These aren’t difficult questions. You should instantly know the answer to them. I know conventional wisdom says otherwise, but come on, we aren’t that fucking mysterious.

Now, if your larger question is whether you have the balls to approach me in the first place, that’s entirely up to you. Just do us both a favor and have your exit planned in advance. Trust me, you want me wondering where you went, not wondering why you’re still talking to me.

On vulnerability

Long story short, my usual pattern of meet a guy, hook up once, part ways forever changed when I met a guy, hooked up once, and then kept hooking up, drunk and sober. We never had a “talk” about “where things were going” because initially, he was more into me than I was into him. But once I started liking him, I felt like he could almost smell it, and he became less interested. We went from seeing each other every other day to once or twice a week—is it ending and I’m too dumb to realize it, or is this just how things are? I’m afraid to be the vulnerable one in this situation—I wanna know if it’s over so I can move on before he does.

Oh, grow up.

God forbid you should have enough self-respect not to play silly games, but since you insist on acting like a small woodland creature, you might as well scamper away now.

Then again, maybe you could stick around, accept the fact that you’re already vulnerable, and practice your relationship skills like a woman instead of a girl.

Quit treating him like an opponent and start treating him like a partner in crime. Celebrate the fact that you might like him, and don’t fear letting him know. If it doesn’t work out, it’ll hurt for a hot minute. So what.

Vulnerability is not the same thing as weakness.