Reply All … And Other Ways to Tank Your Career

Love is in the air … and in the copy room, in the cafeteria, in the gym. Do you know what you’re getting yourself into?

Last month, my friend Pete called to tell me the good news: He had landed the job of his dreams! A week later, after attending a happy hour with his new coworkers, he called me in a panic. “Yeah, so this dream job of mine has truly become a slice of heaven!” I couldn’t help but laugh at his sarcasm. Of course I know that a certain amount of disappointment follows starting a new job. Things aren’t always as rosy as they seem at first.

Imagine my surprise when I realized that he wasn’t being sarcastic. Turns out that nearly every single person he works with, from twenty-five to fifty-five, was attractive. He then went on to list the names of at least seven girls on whom he had developed office crushes. I was happy that my friend’s dream job could possibly lead to meeting “the one” but I warned him to tread carefully and keep his crush list private for now.

I didn’t want to rain on his parade, but office relationships are not the same thing as relationships that can develop after meeting someone at a bar or being set up by friends. In the workplace, the rules of dating are totally different. In fact, forget everything you know about dating in general. The office is not a playground for your hormones or a frat party where everyone is gathered in one area just to hook up. At work, dating is a far second to the real goal of being there. Dare I say it … work?

Don’t misunderstand. I’m not a downer on love. In fact, I’m a huge romantic and my motto is not only that love is in the air, but that it can easily hit you when you least expect it. The issue here is that an office relationship is a serious matter that can affect not only your social life, but also your job, your livelihood, and your professional reputation. The good news is that you can have a successful relationship (or more than one) while being a productive employee. It’s all about timing.

Wanting to date someone you work with is bound to happen. If a new attractive person joins the team, everyone will be thinking the same thing: “Are they single?” And if you are single too and begin to develop feelings, you will most likely start to wonder how you’d go about asking out the new office hottie. However, this takes a lot more than simply putting on your nicest outfit, smelling delicious, and having a killer opener (please, don’t act like you don’t have an opener).

Modern Manners Guy’s Top 10 Tips on Workplace Relationships

Tip #1: Is It Worth It?

Asking someone out in the office, like deciding to wear your “Charlie Sheen for President” T-shirt in public, comes down to one question: Is it worth it?

Understand that asking out a colleague—even if you don’t work together closely—will have a huge impact on your professional career. I’m not trying to say that you will be fired or sequestered to a basement dungeon, but many companies have strict rules on interoffice dating. With that, you have to weigh the pros and cons that come with following your heart (I hope that’s what you are following!). Weighing out what can happen (rejection, acceptance, office gossip, disagreements, etc.) versus the potential upside is incredibly important. So before you muster up the courage, step back and take a good look at what you’re getting yourself into. Ask yourself, “Is it worth it?” and “Can I handle what could happen?”

If what you’re looking for is just a random hookup, then I suggest you fish someplace other than your office pool. The phrase “Don’t shit where you eat” comes to mind. Do you really want to put yourself in the position of being bad-mouthed by a spurned ex who happens to have the boss’ ear? Not wise.

How to know if the person is worth the risk? Test the waters before jumping in. Become better acquainted to see if you’re actually compatible before you suggest a romantic outing. Table the romance for a bit and really find out if you actually have things in common. Mention a book you recently read, a film you saw, a band you like, and then see if their responses line up with yours. If they hate all the things you love, then perhaps it’s not worth it. But if this person is someone whom you genuinely like and who seems to return the favor, then perhaps it’s worth it to take the plunge and see what happens. The more time you spend with them, the better you can figure out if you want to take it a step further. In the end, I hope your heart gives you the answer you’re looking for.

Tip #2: The Friend Zone

We’ve all been in this situation: You’re friends with someone and they’re awesome. You have a great time together, you like the same things, you share a sense of humor. Everything’s peachy … except that you’re dying to make things romantic but the other person has no clue. You’re trapped in the Friend Zone.

Ah, the Friend Zone—that agonizing relationship in which every time the object of your affection calls you a “friend” it feels like a slap in the face. Yeah, that feeling. In fact, most of us would probably take that punch over being called a friend over and over again by the person of our dreams, while they go on and on about someone else they’re interested in.

If you’ve never been in the Friend Zone, here is a sample of how some conversations go: “It’s so nice to have a friend like you who I can talk to about [insert name here]. I mean, only if they were more like you, and were such a good friend, it would be the perfect relationship!” In case you weren’t counting, that’s two direct friend references.

Just in case there’s any confusion, the Friend Zone does not discriminate. It is a quiet little town where both men and women visit in equal measure. In the workplace, where you get closer to people much faster than in the outside world since you’re around each other constantly, you may find yourself passing through the Friend Zone pretty often.

Despite the immediate and daily closeness to a coworker for whom you’ve developed feelings, you can’t let it affect your job. This isn’t middle school where you spend all day jaw dropped, staring at the person of your dreams. Doing that will get your fired. Being in the Friend Zone is not the worst thing in the world so don’t let it cloud your judgment and productivity. If you want to cross that line, that’s fine and I always encourage you to follow your heart (just check out Tip #1 to really figure out if it’s worth it). However, in the end, office romances are tougher than normal ones and sometimes being just a “friend” is actually a blessing in disguise.

Granted, settling for friendship is not ideal, but building close friendships with people at work is never a bad consolation prize. Don’t write someone off just because they don’t see you as “The One.” However, if you’re really dead set on leaving the Friend Zone and entering Romance City, then don’t stick around to listen to how the love of your life and their new partner enjoy acting out scenes from the newest edition of the Kama Sutra. If it annoys or upsets you to hear about this person’s love life without you in it, then I recommend you pack your bags and leave the Friend Zone at once.

Tip #3: Dating Your Coworker

As I discussed in Tip #2, if you enjoy—or can handle—the sweet and succulent pain of rejection that comes with being just a “friend,” well, good for you. Don’t get me wrong, having friends is part of what makes life wonderful. However, you are in the minority. Most of us just can’t handle seeing yet another photo of our crush’s new guy/girl on our Facebook feed. So let’s say you’ve decided to cross the line from friendship to romance, you’ve weighed the pros and cons of taking that risk, and you’ve come to a decision. Now, it’s time to act.

First things first: Asking a coworker for a date should not happen at work. For one thing, the office gossip factor will always make the start or progress of a relationship more stressful (see chapter 3). Also, no cubicle or office is so private that others won’t catch on to what’s happening. “Why was Mitch spending so much time by Liz’s cube?… You know, they’ve been awfully close lately…” Trust me, this type of rumor-mongering occurs pretty often, even if you aren’t dating at all!

Secondly, and most important, dating in the office is not something that comes with the paycheck; it’s a perk. Your boss does not have to allow it if they don’t want to. In fact, many companies have strict rules prohibiting workplace dating entirely. So if you want to ask someone out, do so outside the office—either at lunch with just the two of you or at a separate event. Maybe it takes some more finesse to get the person alone, but it’s essential. And when you do ask, be mature enough to keep this between the both of you. No one else has to know until you’re ready to go public.

If all goes well and you start dating, it’s proper to let your boss know. True, your boss doesn’t have the right to tell you how to live your life, but this is their turf. A romantic relationship will inevitably affect the dynamic of the workplace, which means they have a right to know about it. The boss will appreciate your openness and maturity in revealing the situation and doing so will most likely not raise any red flags (unless you work at a stuffy place where any colleague coupling is forbidden). But one key thing to remember when dating someone at work is that productivity trumps romance. If you had a fight the night before and can’t work together the next day because of it, that’s a problem. If by dating someone you spend more time in their office than at your desk, that’s a problem as well. If you use your position with your partner as leverage to improve your status in the company, that is an improper use of your relationship, and it will likely come back to bite you.

Tip #4: PDA in the Office

Whether it’s true love or a short-lived affair, when you’re dating someone you want to show them how you feel at every opportunity. When it’s in the office, you’ll get coffee together, have lunch, and generally spend more time than normal in each other’s space. Makes sense, right? So you head down to the cafeteria, grab a table for two, or flirt around the coffeemaker in the kitchen. However, that’s where it should end. The company cafeteria is not a romantic getaway where you get to cuddle up together in a booth. There is a time and place for public displays of affection (PDAs) and lunchtime on company property is neither the time nor the place.

If you’re in the middle of Central Park having a picnic and love is in the air, there’s no reason you and your special someone can’t “enjoy” your time together (clothes on though, folks). Or if you’re dining at a nice restaurant and want to pull your sweetie close to you like a cheesy jewelry commercial, then go for it. However, when you are at work the level of PDA should be toned down drastically. And when I say “toned down,” I mean just don’t do it. This isn’t high school where people feverishly rush to make out in dark corners during the break between classes as if they’ll never see one another again. When you dine in the office cafeteria, make your professional side shine brighter than your burning passion. The same goes for groping in the kitchen. It’s just tacky. Save it for after hours.

Tip #5: Dating Your Boss

By far, the most complicated interoffice dating situation is when you’re dating someone you work for—or someone who works for you. This is the ultimate recipe for disaster. Even if the boss is the most respected, forward-thinking person in the world, and the employee in the relationship is the smartest and most professional, there will always be an ethical gray area when you mix business with pleasure (sorry, couldn’t help myself). No matter how well you carry yourself in the workplace, all the other employees will automatically assume that there’s favoritism and this assumption will color your every interaction with colleagues.

A Modern Manners Guy fan named Rob e-mailed me about a sticky situation. He was dating his female boss. They hit it off from day one and despite a five-year age gap (which is not a lot), found that they had similar tastes. So, long story short, he approached her tentatively, asked her out for a drink after work, and they began dating. They kept it quiet for four months until they finally came out to the rest of the office. They didn’t announce their love via skywriting or in a mass e-mail, but they simply stopped sneaking around and if anyone asked, they would happily admit to the relationship. She cleared it with the other top executives, which was the proper thing to do. Kudos to both Rob and his boss for having the courage to be up-front!

Although Rob’s colleagues were happy for him, it quickly became clear that they viewed him differently. People got quiet when he walked into the kitchen, or if they passed him in the hallway. When there was word of a promotion in the office, everyone assumed that he was instantly the top candidate. He felt as though everyone was judging his—and the boss’—professionalism based on their relationship.

Now, as sad as his coworkers were, their reaction is unavoidable. It’s the same thing as working with the boss’ family member; no matter what they do—good or bad—everyone knows that the emotional attachment to loved ones has the potential to cloud judgment. I mean, let’s say you worked at Rob’s company and suddenly extreme budget cuts were announced. If you were fired while Rob’s job was safe, you couldn’t help but think there was favoritism afoot.

If you are dating your boss, the proper thing to do is to remove yourself from their immediate report. Wait, wait, wait, I’m not saying you have to quit! But if you are dating—not married, not engaged to—someone who signs your paycheck or is in control of your career, emotions will always get in the way. That’s why it’s essential to act maturely and try to maintain a clear head. So try to alter your position to work for someone else. Chances are, your boss will be able to pull some strings.

Tip #6: The Unofficial Relationship

One of the questions I am asked most often is about relationships that are not quite “official” yet. You know what I’m talking about: the time period following a few dates or hookups when you log onto Facebook every day, wondering if your special someone had changed their status from “Single” to “In a Relationship” yet. Until they publicly announce this monumental shift in their status to their closest 2,000 “friends,” or heaven forbid you both actually talk about it, you’re stuck in that awkward purgatory known as the “unofficial relationship.” And to make matters worse, if this is happening with a colleague, you have to see them every day at work and be reminded of the unspoken question. So you walk on eggshells around them, not wanting to be too clingy, but then again, not wanting to seem uninterested. It’s exhausting.

If you really think about it, the time you’ve spent with someone you’re dating at work by far surpasses any other non-workplace relationship of the same length. I mean, when you’re dating someone you met outside of work, you only see them at night and on the weekends. If it works out, you may meet up for lunch, but that’s rarely the case. So a relationship in the office tends to run at an expedited rate, just because you see the person more frequently. For this reason, it makes jumping from “Where are we?” to “You’re the one!” seem somewhat rushed.

But it shouldn’t.

In any relationship, the issue of “time” is always looming over you:

• How often should we see each other?

• When is the right time to introduce them to my friends?

• When can I post pictures of us together on Facebook?

• How long before we have “The Talk”?

If you date someone outside of the office, it will take longer to feel them out and really learn if you’re compatible. But if you spend the majority of your day with someone, there’s a faster learning curve. You’ll be able to see them in a rainbow of emotions and situations (stressed, happy, mad, nervous, quiet, talkative, etc.). This may actually be a saving grace because it’ll allow you to form a quicker opinion on whether this will work out or not.

Nonetheless, it still doesn’t mean you should rush to go from unofficial to official. But if you do see them in an unflattering light, this is a good time to go from “unofficial” to “next!” Timing is key in relationships and there is nothing wrong with being unofficial until you are both ready to change status.

Tip #7: The Random Office Hookup

Man, oh man, was that holiday party awesome! The venue, the music, the drinks … oh yeah, the drinks. Nah, you didn’t have that much … or did you? And damn it, wouldn’t you know, your roommate apparently snuck into your bed and is now sleeping next to you. Wait … wait a second! Oh, that’s right, it’s your coworker from the marketing department. Remember?

As we talked about earlier in this chapter, being attracted to someone you work with is natural and wanting to ask them out is going to cross your mind. But what happens when you skip the “asking them out” step and jump right into “making out”? This is what I like to call the “Random Office Hookup” and it rarely ends well.

Like the unofficial relationship, there is a level of awkwardness that occurs in both scenarios. However, in the unofficial relationship, you don’t regret going to lunch with someone because you clearly made plans and are both on board. The random office hookup though, well, therein lies the problem. The random office hookup is not as thought out and planned as other dating situations in the office. In fact, it’s not planned at all!

You were both having a little too much fun, one thing led to another, and now you have something totally different to talk about at the water cooler than the weather. But talking about what happened is the proper way to handle things. This conversation does not have to be lengthy either. Don’t feel like you need to go to couples counseling! Simply step away from the spying eyes at the office and discuss what happened. This can go in one of two ways:

1. If you thought it was a mistake, say, “Look, about last night … I’m not quite ready for a relationship. I’m sorry if I led you on. I didn’t intend to and I apologize.”

2. If you want to take things further, say, “Look, about last night … I’m actually glad it happened and I hope to see you again. But let’s start with a coffee after work next Thursday. Does that work for you?”

And of course you’ll both say that this type of thing “never happens to me.”

Right. Sure.

However you handle the random office hookup, whether you view it as a mistake or a miracle, you have to talk about it with your coworker. Dating in the office is serious for your career and you don’t want someone to view you as a “snake” or even a “coward” for running from the situation. Grow a pair, step up, rip off the Band-Aid, and other clichés.

Tip #8: How to Handle Being Stood Up

Modern Manners Guy fans who have e-mailed me about being stood up all voiced similar feelings: “It’s so embarrassing!” … “I felt betrayed” … “We were just finalizing plans that day and then they don’t show up!” And if the person who stood you up is a work colleague, someone you have to face every day, it burns twice as much.

If this has happened to you (and if it hasn’t yet, it likely will in the future), take a page from the Steve McQueen playbook. The film legend was known as the “King of Cool,” which is pretty much the most badass nickname in Hollywood history. Although no one can pull off the calm swagger of the King himself, there’s a lot to be said about being able to keep your ego and temper in check when faced with an embarrassing situation like being stood up.

I know you probably spent all day thinking about your date, from the clothes you’ll wear to the conversation you’ll have. But then you find yourself waiting at the restaurant or bar for ten minutes too long … then fifteen … then twenty … then thirty! You check your phone and get nothing. You check your e-mail—nothing. This is the digital age, when smartphones rule all, so there is no excuse why someone can’t get in touch with you (unless they’re stuck underground).

Then slowly, as much as you wished it wasn’t so, it dawns on you that you’ve been stood up. Do you stay at the bar, get wasted, and rant the no-show’s name to anyone who will listen? No way! In times like this, remember McQueen and play it cool. Do you think Steve ever got all bent of shape when he was stood up? Hell no! Okay, so maybe that didn’t happen to him very often, considering that he was one of Hollywood’s most epic sex symbols. But my point still stands. You don’t have to be a gorgeous celebrity to keep your cool.

First off, realize you’re not the first to be stood up, you’re not the last, and sadly it may happen again in one way or another in your life. Did you waste your time? Yes. Does it suck that the person didn’t have the basic manners to call and cancel? Absolutely!

However, that is where the emotional roller coaster should end. If you allow yourself to dwell on the situation, it will only make you more upset or bitter. I recommend staying at that bar/restaurant, but instead of drowning your sorrows in several rounds of Maker’s Mark, call up one of your friends to meet you. Heck, call two or three. Don’t waste the outfit and make it a night out. Order the nicest dish on the menu and enjoy the good company. And if that deadbeat ever does call back to apologize, tell them it’s okay—you had a great time without them! And no, you don’t want to reschedule, thank you very much.

If you’d still like to give the person a chance (it’s possible that some unforeseen circumstance, like a death in the family or a cat drowning, actually prevented them from getting in touch), you can save face by leaving them the following message: “Hey [name of rude person], I thought we were supposed to meet at the restaurant at 7:30. I’m guessing you got held up. Don’t worry, it’s cool. I hope everything is okay. Just call me another time and we can reschedule. Have a good night.”

What you’re doing here is giving them a chance to explain themselves when they call you back. If they don’t, then you’ve behaved like the bigger person and know that they don’t deserve your time. Win-win!

The business world has a cruel corollary to being stood up. It’s called The Corporate Ditch, and it happens when you’ve tried for a while to get a meeting with someone for business reasons and, after finally nailing down a meeting time, you are stood up. Granted, this is not a romantic event, but being stood up for a business meeting still burns. You’ve done your research, you’ve prepared your pitch, and you’ve waited all week to finally, finally, have this meeting … only to be greeted with a voice mail. So what do you do?

Don’t rant. Don’t send an angry e-mail that you’ll regret. And definitely don’t burn bridges. Instead, leave a casual voice mail message to let them know you understand they may have gotten busy, explain how much you looked forward to the meeting, and set another time to meet. Try something like, “Hi [name of rude jerk] I guess you got held up this afternoon. Not a problem. I’m going to head out because I have another meeting across town, but let’s plan on getting together next Tuesday, same time and place. Does that work? Let me know. Thanks again.”

This tactic forces a response. So whether they call back and accept the new meeting time or refuse, at least you’ll know exactly where you stand and won’t waste any more of your valuable time.

Tip #9: How to Handle a Workplace Breakup

I’ve said it before and I’ll say it again: One of the most important rules in business is “don’t burn bridges.” That means it’s always best to maintain civil, polite relations with people after ending a relationship (of any kind). This is even more true for ending a workplace romance. The last thing you want is to be known as some heartless creature who callously breaks up with their girl/boyfriend via text.

A friend of mine recently told me that he was ending a relationship. When I asked how, he said, matter-of-factly, “It depends. Text. E-mail is always good. Or just stop calling. She’ll get the idea.” As you can imagine, his now ex-girlfriend did not quite “get the idea.” After hearing my friend’s pathetic, cowardly means to an end, I was shocked. What happened to us? Is this the new norm? Have all the John Cusack and Julia Roberts movies led me down a path of naïveté?

Option #1: Text

Before we get to that question, let’s establish something about texting: It’s the lowest and laziest form of communication. Alexander Graham Bell invented the telephone because typing letters wasn’t efficient enough. Now, over one hundred years later—when we have cell phones and Internet in the palms of our hands—people find it necessary to revert back to the 1800s and type a message. Do you see the irony?

The texting breakup has become stuff of pop culture legend, made famous a few years back when Taylor Swift claimed that her Jonas Brother love ended their romance via text. What was this guy thinking? I’m not just talking about the fact that this girl has a face sent from heaven, but Jo-Bro, this girl will make you (even more) famous if you mess with her heart! And not in a good way. This is not news. But I digress.

If you are going to ruin someone’s happiness for the day (or weekend … or month), texting is not the way to do it. A text breakup casts a nasty shadow on the entire relationship, as if to say it was never that important anyway. No matter how eloquent you try to make a text breakup, this is how it reads: “Hey, there, I’m about to walk into the office but wanted to tell you it’s just not working for me. Best of luck. Hope we can still be friends?” Yeah right, friends? Are you kidding me?

If you’ve just been dumped by text, delete it immediately and try to move on—even if moving on means a carton of Ben & Jerry’s. This type of cowardice does not deserve a response.

Option #2: E-mail

A breakup text’s slightly nicer, but still tacky, cousin is the breakup e-mail. You can write pages of reasons why you are ending the relationship, but it won’t help—you’re still a wimp if you don’t have the cojones to look the person in the eye. The only upside to the e-mail breakup is that it’s a step up from the text breakup, which is like saying a kick in the head is a step up from a kick in the crotch.

Yes, people tend to be more open and honest through e-mail than in person, but that doesn’t make ending things through e-mail any better. My friend Erica told me she prefers to do it this way because it “Hurts her less.” Hurts her less? What about the poor sap whose heart you just destroyed? The dumpee always gets hurt more, no matter how guilty the dumper may feel. If you’re the e-mail dumpee, don’t reply right away. First of all, you are pissed—which you should be—and second, it will drive them crazy waiting to hear what you have to say. Bonus!

Option #3: Phone

As I said earlier, the telephone was invented to make communication easier and faster, but that does not mean it should be in your breakup arsenal. This is the pound-for-pound world champion of rude relationship behavior. I mean, how old are we?

You should never end a relationship by not calling. It’s a colossal step back in our evolution. Instead of falling off the planet, try instead to—drum roll—just be honest! Oh yes, honesty and consideration, the little things that separate us from beasts in the wild. By being honest you’ll save yourself tons of frustration. Chances are you’ll run into this person again (especially if you work together) and the last thing you need is for them to remember you as the one who never called, e-mailed, or—and I can’t believe I’m saying this—texted back.

Option #4: In Person

It may be hard, but the only truly proper way to break up with someone you’re dating at work is in person. You have to make things clear, concise, and final. Simply tell them that you just don’t feel the way you did before. Tell them it’s best to end things now before it goes on and they end up hating you. Never say, “We can still be friends.” It’s lame and weak and if you are meant to be friends, it will turn out that way—but it’ll be the dumpee’s job to decide if they’re interested in your friendship.

If you’re dating someone at work and you don’t want to be involved anymore, tell them you are not ready for a full-on commitment. Yes, you thought you were when you started the relationship, but realized you need to figure things out for yourself and don’t want to make things weird between you two because you work together. Whether it lasted a week, a month, or even a year, let them know you tried but just weren’t ready. They won’t like that answer and may feel like you were leading them on, but it certainly beats simply disappearing. Because nothing says revenge like a spurned lover going to HR and saying the two magic words that can derail your career forever: sexual harassment. (What did you think I was going to say?)

“Really, Kenny, really?!? An e-mail breakup? I’m sitting right here!”

Being up-front is not always the easiest way, but in the end it’s the honorable thing to do. I guarantee you, if you cared for them at all, they will appreciate it (eventually). Just note, they may throw a drink in your face, so duck and cover.

Tip #10: The Serial Office Dater

As we’ve seen, dating in the workplace has its pros and cons, which you must take into consideration whenever you decide to jump into a relationship. You must also take into consideration how many times you jump. Sadly, if you are known as the serial office dater, it may hinder your chances of finally meeting the person you are truly meant to date because they’ll think you’ll burn right through them like you did with the rest. Yes, people talk. No, nothing is sacred. Don’t expect anything to stay hidden for long in the workplace.

The serial dater takes two forms:

1. Someone who doesn’t intend to become a serial dater, but when you spend forty to sixty hours a week in one setting, you are bound to run into people you are interested in. It’s only natural and perfectly understandable.

2. Someone who treats their dating life as a game, with the end goal of adding as many notches to their record as possible.

For one, there is no harm in dating multiple people in your office—not at the same time, of course! But given how much time you spend with your colleagues versus with strangers in bars, it’s bound to happen. For example, my coworker Andrew told me that he was worried about his reputation because he’s dated six colleagues in five years. He is a clean-cut, well-respected, attractive, fun guy, so dating has always been fairly easy for him. But finding the right one was not. And that’s what he was looking for.

Is that his fault? Should he be labeled a serial dater simply because he wants to fall in love? No, he should not. And the only way to safely date at work and keep your reputation from going south is by following the tips I mentioned earlier in this chapter:

1. Weigh the pros and cons of dating a particular person.

2. Minimize the office gossip that comes about as the result of your relationship (aka, provide them as little information as possible to stir rumors).

3. Don’t break up badly. This could be the ultimate reputation (and career) ruiner.

4. Never intentionally lead someone on.

Bottom line is that an office relationship must be handled more delicately than any other one, so treating everyone with respect and kindness is the only way to pull off dating multiple people in the office.

However, if your only goal is to be able to say, “Yeah, I did that,” well, guess what—you’re a pig. Oh, and I hope you get fired, too. Man or woman, anyone who thinks that dating is only for bragging rights has clearly never evolved past age sixteen. Even at that age it’s foul, but as an adult? Come on, grow up. If you want to go on a rampage of sexual escapades, go right ahead. But if you think you can pull this off in the office, you are wrong. Not only will you look bad in your peers’ eyes, you could also easily be fired for creating an unprofessional working environment. Plus, when you really do fall for someone, they’ll want nothing to do with you, given your “player” reputation.

MODERN MANNERS GUY QUIZ

After two months of dating someone in your office, you realize it’s just not working out. So one night after work you e-mail them and end it as politely as you can. The next day, they are still e-mailing you at work asking “Why? Why? Whyyyyyyy?” You can’t get anything done and are afraid to even see them. How do you deal with this situation?

A Take the person back after e-mail #52. After all, they did just score front-row tickets to the concert you’ve been dying to go to. What’s another couple of weeks?

B After realizing this person is a Level 1 whack-job, tell your boss and HR about what happened. Present the e-mail thread as proof and let them know that this situation is now affecting your job performance.

C Walk over to their desk and “rip them a new one” in front of everyone to make sure they firmly understand where you stand on not wanting to pursue the relationship.

D Ignore them completely, hoping they’ll just get the hint.

Answer

B … with a hint of D. Allow me to explain.

Let’s face it, we’re all much quicker to jump into bed with someone than we are to do a background check to see how (in)sane they are. And as many of us know all too well, sometimes the craziest ones are the best looking, which tends to dim the freak-o-meter until we realize they’ve caught us in their web of weirdness. Happens all the time. So don’t feel bad that you didn’t see this coming. However, just because they can’t handle the breakup doesn’t mean you should accept angry e-mails, rants, or any other borderline crazy antics. Immediately tell your boss and HR that this is becoming an issue. If they e-mail you asking why you don’t love them anymore, that’s understandable. But if it’s name-calling or threats, don’t wait to take it to your manager. Even if you don’t want HR to “take action” yet, at least let them know it’s starting to affect your work. That’s something they will definitely care about.

In terms of sprinkling a little D into your approach, what I mean is that you don’t freeze them out completely, but you don’t want to bait them into a bigger argument by constantly feeding their e-mail thread. Don’t get sucked into a discussion, over e-mail or in person. Let them e-mail you until their fingers hurt, but don’t retaliate and turn this little fire into a barn burner. Chances are, this can lead you down a road with no end and also make you say something out of anger that you may regret.

MODERN MANNERS GUY’S WORKPLACE RELATIONSHIPS TOOL KIT

1 THE OFFICE PRENUP. No, I don’t mean an actual written document but an informal agreement. Like Lisa Loeb said, it’s always good to know where you stand before the relationship so if it does end, everyone leaves with what they brought to the table. This means if you are working closely with someone you’re dating, make sure that you both understand your contributions so there’s no finger-pointing later on. Being partners at work and partners in love is not the same thing.

2 BREAKUP DOCUMENTS. Breakups always become a case of “he said, she said.” That’s why you should always save the e-mails from your office romance, especially ones where the “true self” of your (in)significant other comes out. This way, when they say, “I never said that!” you can show them that “Well, yeah, you kinda did.”

3 KEEP YOUR OWN SPACE. I once had a colleague who let his girlfriend use his big corner office as a “hideout” to unwind or have lunch in during the day. Since they were dating, he didn’t mind her popping in while he was on a call or working. However, she made herself more comfortable by inviting friends, as if it was her office, too. When the relationship ended, she still felt entitled to use his office as she did before. Sadly, this is not how it works. Here’s a perfect example of why the Office Prenup from Tip #1 is a good idea.

4 IXNAY THE PDA. When you’re in love, you want to shout it from the rooftops. However, there is a time and a place for that and work is not it. So save the PDA for after hours and weekends. You might actually find it exciting to “abstain” during the day—and rip each other’s clothes off at night. You know what they say: absence makes the heart grow fonder.