CHAPTER 19: DATING WOMEN
There are three possible parts to a date, of which at least two must be offered: entertainment, food, and affection.
—Judith Martin, advice columnist
Dating (or, to use the boring science-y term, “the human courtship process”) has been around, in some form or another, for a long time.
Over thousands of generations, the purpose of a date (courtship) hasn’t really changed much. Dating is an opportunity for you to evaluate a woman and for her to evaluate you. A date is just the most efficient context for the interplay of eye contact, conversation, humor, fun, and sexual chemistry that may or may not escalate into mating.
Yet you probably suck at dating. Most guys do. You don’t know where to take a woman, for how long, with what expectations. You don’t know how to gauge her interest or comfort level. In the back of your mind, you’re hoping—half seriously—that when the check comes she’ll just come out and tell you what level of sexual interaction you’ve earned for your effort. And it’s only gotten trickier with social norms in flux, one-on-one dates giving way to group hangouts, and women ever warier of cheats, liars, and players.
And still, women want to go on dates. With you idiots, of all people! That’s how ingrained courtship is in human nature, and how ingrained dating is in our culture.
A woman wants a public, romantic, memorable demonstration of your interest that makes her feel desired and that she can brag about to her girlfriends—even if she never wants to see you again, even if all you add to her life is a new item on her “deal breaker” list. A couple of drinks and some food after a hard day at school or work is just a nice bonus (if it goes well) or the cost of doing business (if it doesn’t).
Here’s the interesting thing about dating, though: she doesn’t really care very much where you go or what you do. She doesn’t care about the wine or food. She can entertain herself without you. She can drink and feed herself without you.
The whole point of the date is to provide a pleasant context for courtship, for the mutual display of fitness indicators, the sharing of life stories and the testing of sexual chemistry. It is a test you are both giving each other, and hoping the other passes, so you can move on to the fun stuff together.
If you really hit it off (if you both pass each other’s mate choice tests), it doesn’t matter much where you are, what you’re doing, who else you’re with, or how much it costs. If you’re funny, charming, and engaging, you could be eating soggy fries and drinking shitty beer in a bowling alley while a gang fight erupts around you, and it won’t matter to her.
In fact, if a long-term relationship develops, she’s going to look back on that melee with great fondness as your romantic first-date story: “Four people died in a hail of gunfire and screaming, but all we could see and hear was each other!”
The relative unimportance of what you do or where you go even extends to bad dates (when either of you have failed the test). When women describe bad dates to their friends, they hardly ever mention the quality of the food, or the movie, or the miniature golf course. Their focus is on the guy and the emotions he evoked: how he made them feel uncomfortable, awkward, obligated, disgusted, or freaked out. It’s rarely ever the venue or the menu that is the straw to break the date camel’s back. If she does bring it up to her girlfriends, it’s usually only as an exclamation point on the date’s death sentence, “And if his conceited, know-it-all blathering and awkward staring at my chest weren’t bad enough, he took me to Cracker Barrel and there was a chest hair in my pancakes!”
A woman can have an amazing date in a shitty dive bar in Cleveland if you are funny, fascinating, and thoughtful. She can have an equally horrible date at Eleven Madison Park (one of America’s most incredible restaurants) if you’re a boring, servile wimp or an obnoxious, loudmouth asshole.
This chapter is designed to give you ideas for things to do with women that are interesting and fun for both of you and that allow you to display all your positive attributes.
GRADING THE COURTSHIP TEST
If dating is a kind of mutual courtship test, then the traits and proofs we display toward each other through our physical and verbal behavior are the answers we give and use to grade each other. That grade is, more or less, your mating decision.
“Holy shit, I could marry this person!” (A+)
“That was great, I’m looking forward to our next date.” (A-)
“Wasn’t bad, probably worth a second date.” (B)
“Thanks but no thanks.” (C)
“Erase my number from your phone and my face from your memory.” (F)
If both people give each other what amounts to a B or better, a second date’s pretty likely; if it’s an A+, the date’s likely to last until sunrise. If either one of you is playing at a C-level or below, there’s almost certainly no future for you guys—at least, if you are approaching dating with a healthy, confident mindset.
If you look at dating like this—as a way to gather information to make mating decisions—then everything else about dating that might have seemed confusing should start to make sense.
From just one date, for instance, you can evaluate each other on every trait and proof we covered in Steps 2 and 3. After a date, ask yourself about these traits and proofs:
Physical Health: Do I find her physically attractive? Is she in shape? Does she have a good body? Does she look healthy and attractive? What about her skin, hair, eyes, and posture?
Mental Health: Does she seem normal and safe, or weird and threatening? Or is she weird in ways I’m not comfortable with? Is she happy, open, playful, and fun, or depressed, paranoid, and unpredictable?
Intelligence: What is the conversation like? Is it fun for both of us? Can she read my signals? Is she listening to me? What topics does she talk about? How does she talk about me? Is she interesting?
Willpower: Does she plan things well? Was she on time or fifteen minutes late with no reasonable excuse? Does she appear to have her life together, at least to some extent? Is she generally neat and clean and organized, or sloppy and disorganized?
Tender Defender: Does she deal with people confidently and assertively, yet kindly and politely? Is she too nice or too nasty?
Social Proof: Does she have friends? Do people like her? Does she do social things? Does she comfortably find her place in new social settings, or does she melt into the background?
Material Proof: Does she dress well, live in a decent place, and have fun experiences? What kind of resources is she bringing to bear on the date? Is she self-sufficient or wholly dependent on someone else?
Aesthetic Proof: How does she dress? Does she have her own style? Does she have style at all? Are her car, apartment/dorm room, and belongings put together nicely? What kind of taste does she have in music, TV, film, art, architecture, and travel, etc.?
Romantic Proof: How much does she seem to like me? How much effort did she put into this date? Is she proud to be with me or is she trying to hide me? Is she taking extra pains to be considerate, chivalrous, attentive, and proactive about my well-being?
Mating Goals and Ethics: What kind of interaction or relationship is she looking for? Do these goals line up with mine? Is there a potential for a relationship win-win here?
Mate Preferences: What does she want in a mate? How do her mate preferences match my traits and proofs? Are her preferences thoughtful and wise, or superficial and juvenile?
Understand that the real objective of dates is not to spend a few hours feeding some cash into the service/entertainment economy; rather, it’s for both people to display their best traits and proofs and to reveal their mating goals and preferences, so they can both make the best possible decisions about pursuing a mating relationship with each other.
This perspective should give you a completely different approach to dating. Now, instead of doing what other people do, or things you don’t like, you can use dates to your advantage.
You can orchestrate your dates to show the best side of yourself. This has the added benefit of making the dates more fun and memorable, which also means women will almost always like them more as well.
WHERE TO GO AND WHAT TO DO
There are so many places and activities that enable you to show the best side of yourself and allow you to get to know each other, but most guys get lazy or scared and fall back on old stand-bys (dinner and a movie; drinks and more drinks) because they’re trying to impress women with all the wrong things.
In reality, a good date can be any enjoyable, low-stress activity that allows both of you to learn about each other and display your best traits.
Just ask yourself the following questions as you run through your date choices. If you have more than three brain cells to rub together, you should come out the other side with some good ideas:
1. Will we be able to talk to each other and touch?
The setting of your date should allow for the right level of physical contact and conversation, particularly early in the courtship process.
Shooting guns, for example, can be a fun date, in principle—especially if you’re good at it and you can teach her to be good too. However, if you’re on a first date and you’re at a range obeying all appropriate safety regulations, there are several barriers between you and getting to know each other—including ear protection and a metal dispenser of molten death pellets.
The last thing you want is for your date to be thinking, “I sure hope he’s not unstable because if we break up and he comes after me with a gun, he’s not going to miss.”
Plainly put, you need to be able to talk to each other on a date. That means no concerts, no movies, no theater, no monster truck rallies, no shooting ranges—at least in the beginning.
Here are a few ideas to get you started:
• Café or coffee shop
• Miniature golf or batting cage
• Chuck E. Cheese’s or similar place
• Museum, zoo, or aquarium
• Hiking
• Carnival or amusement park
• Medium-sized quality restaurant
2. Can you afford it comfortably?
First dates should not be expensive or elaborate; they are about information discovery and trait display. You still don’t know if you like your date or if she likes you, so don’t commit to a big, expensive outing until you at least know that much.
This doesn’t mean you should start on the McDonald’s dollar menu and make her earn her way up to super-sizing her value meal. It just means you should keep your first dates in a range you can comfortably afford, while still showing that your life is together enough that you can afford to do fun things.
As a rule of thumb, given your income, if you couldn’t easily afford to go out on any given first date at least twice a week, you’re spending too much—i.e., you’re giving up too many other potential dates for this one woman.
Follow-up dates can swing in either direction—very cheap (a day trip to the beach) or quite expensive (a three-day weekend in the Bahamas)—depending on your goals, abilities, and resources.
The key in the beginning is to give yourself options and room to show growth. If you max out your credit card to take a girl to the nicest restaurant in town and then a concert with front-row seats for your first date, it’s all downhill from there. Escalating cost on dates is a sign of escalating romantic proof and commitment, so don’t shoot your wad too early.
3. Does it sound fun? Will she want to tell her friends about it?
Women like to share details about dates with their friends and relatives afterwards, like a courtship post-mortem. Your date is not just about you and her; it’s a potential contribution to every conversation in her whole social life. If you add value to her other relationships, then you’ve added a lot of value to her life, and she’ll want to see you again for more.
So when you’re figuring out where to take a girl, ask yourself whether good shareable material is likely to come out of it. Does it have the potential to be distinctive and memorable and to make a good story?
Asking yourself these questions is less about finding super amazeballs places to go on dates and more about avoiding the same boring shit that isn’t very fun and doesn’t allow you to get to know each other. A mountain of spaghetti at Buca di Beppo and the latest superhero sequel at the local multiplex give her nothing to text home about.
Ideally, when her mom calls on Sunday afternoon and asks (again!) if she’s met a nice guy yet, your date will be able to tell her all about you and your awesome date plan. When she goes to school or work on Monday, she’ll be excited to tell her friends about what a great time you both had, instead of anxious about reporting another dud.
4. What positive traits and proofs will this activity allow me to display?
All those painfully awkward first dates you see on TV and in movies? They happen because someone gave those characters horrible fucking advice about what a person is “supposed” to do on a date. Or their screenwriters were lazy about scene-setting.
If you hate fancy food and expensive wine, do not take a woman to a fancy restaurant and struggle to order. There’s nothing more embarrassing than asking what the “pricks ficksie” (prix fixe) is or why you have a spare fork next to the big fork. It will only frustrate you and make you look bad.
Instead, do things that you enjoy and are good at, ideally that overlap with her interests or desires. An ideal date is something fun that you both enjoy. If you both love dogs, take your dogs to the park. If you are both beer snobs, go to a nice microbrewery for a tasting.
You may not have a ton of favorite activities in common with your date, or you may not know her well enough yet to know what she likes. That should not frighten or deter you, because it can actually set you up for a great date. If you know how to do something and she doesn’t, teaching her that skill can make for a fantastic date.
You can take almost any activity you like and turn it into a date if you frame it that way. If you really like archery, offer to take her to an archery range and teach her how to use a bow and arrow. She might not care about archery, but she can anticipate that this date will be new, fun, different, and memorable. It also gives you the chance to show all kinds of positive attributes: physical health, practical intelligence, patience, communication skills, and tender-defender skills.
Whereas the gun range would have been terrifying and made conversation impossible, the gentle “swoosh/thwack” of shots at the archery range allows easy conversation, and teaching her how to draw that bow requires plenty of physical contact.
IDEAS FOR DATES
There is no perfect “right date” that applies to all men in all situations. A twenty-year-old college student who likes video games and sports will have a very different ideal date than a forty-year-old computer engineer who likes math and fine wine, and they’ll be dating different kinds of women. You’ll have to think for yourself, but here are some ideas to get you started:
DATE LOCATIONS & ACTIVITIES
Outdoors & sporty activities
What/Where: rollerblading, playground (swings, slides, etc.), climbing wall, mini-golf, Frisbee golf, kite-flying, walking in the park, bowling, go-karts, hot-air balloon ride, helicopter sightseeing, skydiving, boating, ice skating
Why: Across the spectrum of cost, these activities are all fun, simple, and active, and they allow for conversation. They show physical skills, set you up for easy humor, enable easy physical intimacy, and expose you to a variety of dynamic, challenging environments.
Conversation & brainy activities
What/Where: bookstore, coffee shop, local art galleries, art museums, science museums, history museums
Why: If you’re less athletically inclined and more cerebral, these places allow you to talk easily, showcase your intelligence and openness, and display your aesthetic proof..
Social & group activities
What/Where: Farmers’ market, cooking class, touring a food/drink factory (e.g., chocolate factory, winery, brewery), partnered dance lessons, karaoke with your friends, bar with bar games (e.g., billiards, darts, skeeball, shuffleboard), comedy club, improv group
Why: That old saying that rising tides lift all ships applies very much to socially-focused date activities. If everyone is having fun, you and your date are more likely to have fun too. These dates showcase your social and aesthetic proofs, as well as your mental and physical health..
CREATE THE IDEAL (FIRST) DATE
Too many guys approach first dates as two distinct questions: (1) “Will you go out with me?” and (2) “What should we do?” This approach is a recipe for anxiety.
Add in the question, “What do you want to do?” and it becomes a recipe for failure. That shows zero conscientiousness, zero romantic investment, and zero understanding of female mating psychology.
The key to successfully setting up a first (or any) date is to take the initiative and have a specific plan ready before you even ask her out, so that you’re essentially only asking one question. Besides, you’re the one suggesting a date; shouldn’t you know what the fuck you’re going to do?
This does not mean you issue her an ultimatum: “Dave & Busters, Wednesday, 6 p.m., SHARP!” That’s obnoxious.
Instead, say “I have an idea: I want to take you to tag-team some skeeball at Dave & Buster’s on Wednesday and bankrupt them of their plush toys. I was thinking 6 p.m. Does that sound like fun?”
That shows you have been thinking about her and your time together in a concrete way. And it leaves her with three simple options for answering: (1) Yes, (2) Yes, but…, (3) No.
This is one of the reasons we advocate that you develop a default First Date Plan—something you can do, with only a little modification, with every woman you take on a first date. In designing your default, keep in mind that the ideal first date has three main features:
1. A weekday evening: It happens on a weekday (ideally, Wednesday or Thursday) and starts in the early evening, after work or school, when you’re both free for the rest of the night. This allows you to talk as long as you want but gives both of you an easy, respectful out if things aren’t going well (i.e., you have school/work tomorrow). A weeknight date involves less pressure and expectation than a weekend date, and it leaves your weekend free for people you already know.
2. An escalation option and an easy out: It has an easy and mutually understood end point (like you’re out of arrows at the archery range, or the bookstore is closing) but can just as easily lead to a shared meal nearby if you like each other, so you can talk more without getting hungry, and so you can buy her delicious food.
3. Cheap, but not boring: It’s something you both like doing that you could do at least twice a week with other women.
Keeping one or even two default date plans in your back pocket means you are always ready to not just ask a girl out, but to do it with an attractive degree of specificity.
Contrary to conventional bullshit wisdom, offering a specific itinerary for a date does not make you pushy, it makes you attractive. She’s free to turn down or modify your offer or to make a counter-offer. Remember, women can decide for themselves if your plan makes sense for them, and they can tell you if it doesn’t.
That’s the second part of taking the initiative: listening to and accepting her response. If she is enthusiastic about your idea (she says yes), great, do it.
If she’s not (she says yes, but…), don’t get offended. Don’t take her negative response as a judgment of your character (unless your suggestion was something like going to Olive Garden and then paying a bunch of homeless people to fight Royal Rumble–style for the rest of your bottomless breadsticks). In which case she has probably gone from yes, but… to a flat-out no.
If you haven’t offended her to the core of her being, just come up with another idea. If you want to ask her about things she’s always wanted to try, that is a totally valid approach and works well with a woman who has a good head on her shoulders.
DATING ETIQUETTE
Dating etiquette tends to shift over time with sexual mores and social conventions. What was normal for your parents was probably not normal for their parents and probably isn’t normal for you now, just for different reasons.
It was once right and proper, for instance, to throw your cape over a muddy puddle to ensure clean passage for a lady. That was the sixteenth century. Nowadays, the biggest problem a woman would face in that situation is wondering why the fuck are you wearing a cape?
Setting aside the intricacies and peculiarities of etiquette over time and across cultures, there is one overarching rule that, when applied correctly, will serve you well in all situations. We call it the Platinum Rule. It’s basically the Golden Rule but for people you actually care about, whose brains aren’t exact clones of your brain. It goes like this:
Treat a woman as she wants to be treated (given your new insights into what it’s like to be a woman).
Think of a woman in your life whom you care about, other than your mom or your sister. How would you want some new guy to treat her on a date? Probably with courtesy and respect, right? Of course. So do that, and you’ll be fine. Most everything else will come out in the wash if you and your date treat each other with mutual care and respect.
Now, there is still one lingering “dating” issue in our culture that you need to understand so you don’t get blindsided—the question: who pays, and what does it get you?
The current American social norms hover somewhere between “the man should always pay” and “whoever initiated the date should pay,” but there is no clear, consistent data or guidance on this issue that applies across the board.
That being said, the research does show that the majority of women want men to pay for the first few dates. Why? It’s not because they’re greedy gold-diggers. Well, some are, but very few of them.
It’s because they are unconsciously looking for signals of your kindness, generosity, and material proof. Your picking up the check provides hard-to-fake information about your character and your resources, and that’s important information for her to have.
Most men are okay with this arrangement—or at least they are used to it enough that it doesn’t really register as a choice they are making.
But a surprising number of men believe that paying for dinner and dates is nothing more than a thinly veiled exchange of money for sex. This is total fucking nonsense. The “men” who perpetrate this line of garbage are angry misogynists who spend all their time trying to sleep with gold-diggers because their mothers didn’t hug them enough. Fuck those guys. If you’re one of them, get your shit together. If you’re friends with some of them, give them this book or cut them out of your life. They’re toxic and they will drag you down into a dark hateful hole with them.
Never think of paying for drinks or dinner as a down payment on sex. That sex-for-food exchange instinct is not only invalid for many reasons we don’t need to get into here, but it makes women very uncomfortable (as it should, because it’s creepy). If you are struggling with this, keeping the dates inexpensive early on is a practical way for you to pay without putting any undue pressure on the date.
READING YOUR DATE (KISSING, ESCALATION, SEX)
If there is one area of dating that makes women want to pull their hair out, it’s the inability of most men to read what, to women, are blatantly obvious signals of interest (or disinterest).
They express interest and intimacy through how they dress, talk to you, look at you, sit next to you, and make physical contact with you, and they are hoping you’ll read the signs correctly. That’s why you need to become bilingual, so you can follow both English and “Flirtish.”
Clothes
Even for a first date, a woman usually will choose what to wear very carefully, based on how likely she thinks you are to be a cute one-night stand, versus a month-long fuck-buddy, versus a potential boyfriend. Even if she’s coming straight to the date from work, she probably chose that day’s outfit with your date in mind.
There are some fairly reliable signs she’s already intrigued by you (based on meeting you before, your online profile, or a friend’s recommendation): new haircut and style, a manicure, high heels, little black dress or anything red, a dress or skirt rather than pants, jewelry (necklace, earrings, rings, hair ornaments), makeup, lipstick, stylish handbag. If she wears all of this, that’s about as close as high-quality women ever get to “throwing themselves at you.” They’re saying, “You’re worth bringing out my A-game, don’t let me down.”
More often, though, the cues from her clothing are much subtler and only reliably discernible over the course of the date or multiple dates. For instance, maybe she’s wearing pants instead of a skirt because she knows they make her butt look better than anything else in her wardrobe. You won’t know that until you’re seen her in other things. And you will realize it only when you see her get up and walk to the bathroom and think, Holy Christ, those pants look amazing!
The point is, there are things to be understood from your date’s choice in clothes, but only to a point. So you need to rely on conversation and contact to pick up where the perfect pants left off.
First contact
Touching on early dates is a tricky thing for both men and women because it’s the first real act of physical intimacy and the first foray into personal space. You should approach touching a woman the same way you approach talking to her: be decisive and self-assured, yet gentle and protective, with the casual confidence that will provoke a positive response.
There’s no reason to be hesitant. If she doesn’t want you to touch her, she’ll move away or let you know. The rejection will sting just the same whether you reached for her hand with a gentle, manly grip or whether you flopped your pasty paw out like a wet noodle in the general direction of her elbow.
Unlike sexual innuendo in conversation or texting, there is no plausible deniability in escalating physical intimacy. Either you reached for her hand or you didn’t. Either you put your arm around her shoulder or you didn’t. Any move you make that seems designed to be ambiguous or deniable shows immaturity and lack of confidence and so is much more likely to be rejected.
There are ways to engineer brief moments of contact to help you get comfortable before you initiate a bolder touch: offering your arm for her to hold onto as you walk down the street, opening the front door of the restaurant and guiding her through with your hand lightly in the small of her back, lightly touching her shoulders as you remove her coat for her before you sit down, touching fingers when you hand her something small like keys or the coat check ticket, or helping her draw the bow at the archery range while you stand behind her.
She knows damned well that most of these situations are really just excuses for you to touch each other, but they’re still more romantic than the pasty-pawed elbow-slap mentioned above, and she’ll appreciate that having some plausible deniability smooths the way for more physical intimacy.
Fortunately, women have their own set of signals when it comes to their openness to physical intimacy. They will place their hands or arms close to yours. They will touch your shoulder or arm to get your attention in order to tell you something interesting. They will sit closer to you or lean in to hear you even when it’s clear they can hear just fine.
Your job is to recognize these signals for what they are (NOT accidents) and to initiate the next level of contact when it’s appropriate. When the conversation’s going well, for instance, and you’ve shared a few laughs, and she lightly smacks your hand in reaction to something you’ve just said, chances are she wants you to hold her hand.
This is a big step—at least in her mind—so your decision to either take it (and her hand) or leave it is equally important. If you take it and then intertwine fingers with her after a few minutes, that’s a sign of strong mutual interest. You’re moving from being “on” a date to being “in” a romantic conspiracy that will probably escalate to a kiss.
If you don’t take it, she will give you another couple shots at it, but if you miss those as well, don’t expect the kissing booth to be open when you walk her to the door at the end of the night.
First kiss
If you’re having a great first date with a woman, and she seems like possible girlfriend material, you want to show physical interest in her early, but you want to be patient about having sex. If the conversation is clicking over drinks, you might touch her shoulder or her back if you’re standing in a busy bar and creating space for yourselves like a proper tender defender. If you get some dinner, you might hold her hand for a minute after the main course if the signals are all there.
But don’t try to kiss her until near the end of the date. This is a practical consideration as much as it is a comfort issue. Leaning over your entrees in the middle of a restaurant could end awkwardly or in complete disaster with spilled wine, stained shirts and her hair on fire from the votive candle in the middle of the table.
The ideal first kiss probably happens somewhere semi-private, when distractions have melted away, you’ve both locked eyes, at close proximity, and there’s nothing more to say. If she’s talking nonstop, but standing close to you, that’s because she can’t stand the pre-kiss tension, and that’s the time to just interrupt her and kiss her.
If she’s done something a little embarrassing, like spilling coffee down her coat, or slipping in her heels on the way to your car, she’s feeling vulnerable and self-conscious—kiss her.
And if she’s set up a situation where you clearly should kiss her, like asking you to walk her to her door after the second date and standing near you, looking alternately deep into your eyes and at your lips, then you’d better fucking kiss her, or we’ll fly over there and kiss her ourselves!
Here’s the thing to remember: there is no PERFECT time to kiss her. You make that time, based on the accumulation of attraction signals you have exchanged with her over the date.
Takeaways
• Dating is just the modern incarnation of the human courtship process, designed for men and women to evaluate each other for the traits and proofs we evolved to prefer and find attractive.
• A good date is any enjoyable, low-stress activity that allows you to have fun and learn about each other. It doesn’t have to be expensive or complicated; in fact, it shouldn’t be, in the beginning.
• The ideal first date happens on a weekday evening, allows you (or her) to easily and un-awkwardly terminate or escalate, and is inexpensive but not boring.
• Most dating etiquette is antiquated nonsense. The only rule you need to follow, given your new insights into what it’s like to be a woman, is the Platinum Rule: Treat a woman as she wants to be treated.
• Reading your date’s signals can be difficult and frustrating—the keys are in what she wears, how she talks, where she sits, how she looks at you, and if she touches you. Those signals can guide you through the progression of physical contact and intimacy.