How to Date Your Boss, and 10 Other People You Probably Shouldn't

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Listen, we all know there are people who we absolutely, 100% should not, must not date. Ever. Except... spoiler alert: we do it anyway.

We’re not here to tell you who not to date. You already know, and you clearly don’t care, so it’s a giant waste of our time. Instead we’re here with some sound advice on how you can try to pluck these forbidden fruits without ruining your life. You’re sort of welcome.

Disclaimer: none of this is a guarantee. These are all still horrible ideas.

1. Your co-worker

You spend more time on a weekly basis with these people than any other human you interact with, so sexual tension is bound to ensue. Especially if you’re that rare breed of relatively attractive cubicle dweller under the age of 40 -- aka “office hot.” You’re smart, so you already know this is a beyond horrible idea, but after the fourth or fifth round at happy hour, you literally give zero fucks, and what’s the big deal if you hook up, it’s just sex, amirite??

No, no you are not right. And now you are dating your co-worker. But that’s cool. Keeping it a secret as long as possible is one way to successfully navigate this disaster of a minefield. Not only are you spending eight hours a day with this person, but then you are expected to spend your free time with them. The less you interact at the office, the more you’re going to want to do all sorts of dirty things to each other later. It’s essentially eight hours of foreplay. It’s also totally hot to steal a kiss in the break room when no one else is watching. But try not to be too cavalier in case, you know, you get fired. Plus, the less people know or suspect at work, then the less awkward it will be when you inevitably break up. Which WILL happen. But hey, it’s not like you’re dating your boss.
 

2. Your boss

Aaand you went there. On a scale of 1 to worst possible decision you could make, this hovers somewhere around the worst possible decision you could make. But don’t fret! There are ways to make this work so that neither of you end up on the wrong end of a lawsuit and/or at the unemployment office.

First, obviously, keep your damn mouths shut. At least until you are entirely sure that this is going to be a lasting relationship and not just some sort of taboo “sex-on-desk” fantasy that you both need to get out of your systems. If you do decide this is legit, there are ways to maneuver, but you’re both going to have to learn to be flexible and tolerate a lot of bullshit. People ARE going to talk. They will claim you get the special treatment, even if that is entirely untrue. The gossip mill goes berserk. A lunch here and there is fine, but limit the amount of times you are in his or her office alone with the door shut, even if it is strictly business. Bottom line: this is still your place of work, and should things toe the line between professional and unprofessional, you will have HR and fellow employees on. Your. Ass. Quitting with dignity so you can screw in sweet private bliss is also a valid option.

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3. Your friend’s sister

Congrats, sir, on your impressive set of balls. Hopefully your friend isn’t all murderous about that whole wanting to bang (er, “date”) his sister thing, but all other examples set forth by our nation’s forebrothers show that charting these choppy waters isn’t easy. You’ll have more luck if your feelings actually do extend beyond wanting to do it in the guest room at the family BBQ.

The best course of action is to talk to your homie about all the warm, fuzzy, entirely non-sexual feelings that his sister gives you. The minute homeboy sees you look at his sister the same way you look at the hot bartender or a big pile of wings, your cover is completely blown. If you and his sister have already professed your love to each other, you could approach your buddy together so that he knows everyone is on the same page and you’re not being a creepy perv. Hopefully, your friend just wants you two kids to be happy.
 

4. Your favorite stripper

Just because she grinds up half naked against men all night long for money doesn’t mean she doesn’t have feelings. And she DEFINITELY has feelings for YOU! For this one, you’re going to have to play it entirely cool. Refrain from attending that particular strip club, as you’re definitely going to see things you do not like. Remember that this is her job and you have to respect that. Don’t ask her how many lap dances she gave that night or if anyone at the club touched her, or when she’s going back to school to become a kindergarten teacher. You will not like the answer. Your new GF is PAID to make men believe she likes them. We’re not saying she doesn’t like you. Just make sure the tab at the end of your dates isn’t running you $3K.

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5. Your ex’s friend

The answer to this riddle is pretty simple. How long did you and your ex date? You can totally pull this off if it was just a few months with a conversation peppered with the right amount of “I’m sorrys” and “I just can’t help its.” If the relationship involved years and years and shared apartments and the exchanging of stuff and the coming together of kin, you really need to just let this one alone. If you believe that you and the friend were really meant to be together all along, just know and accept that a friendship will probably die in the process. Avoid showboating, at least for a while. Leave the PDA at home, and hold off on becoming a “we” too quickly.
 

6. Your best friend

So your best friend is a member of the opposite sex, and one day she takes her glasses off and lets her hair down, or maybe you saw her get out of a swimming pool in slow mo, and you realize she’s actually hot. Great. Now you have to tactfully get yourself out of the friend zone, which is a near-impossible feat previously mastered only by Freddie Prinze Jr. Fortunately, in the real world, much already works in your favor. You know pretty much everything about her. She has probably even complained to you about how “men are the worst” (except for you because you’re just so sweet), and you know what it is that makes her tick.

Try starting slow with an unexpected compliment. Catch her off guard by noticing something you don’t usually notice, and get her thinking that you see her in a different light. If she warms to your advances, tell her you’ve been thinking about her and would like to get a drink with her. If she does reciprocate, this relationship is going to go from 0 to Seriously Committed faster than you can say She’s All That, so be prepared to start on date 15. You could also both have a few drinks and then just go for it. Perhaps she has some long-harbored lusty feelings for you, as well.

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7. The guy/girl you hooked up with on vacation

You met on a Caribbean beach at sunset and proceeded to hook up in a hot tub over glasses of Champagne while opening up about your feelings. It was “the best night of your entire life,” you’ll tell your friends with a melancholy sigh while they roll their eyes. You’re confusing a romantic, idyllic situation with actual legitimate feelings. However, if you’re going to see this one through to the fast-approaching end while navigating a long-distance relationship with someone you met one time, the important thing to do is to keep regular communication. Text frequently, make use of Skype so you can talk about actual real life, and send the occasional nudie pic/vid to make sure you don’t get long-distance friend-zoned. Oh, and get your ass on a freaking plane to visit. This will go absolutely nowhere if neither of you is willing to go the very real and legitimate distance.
 

8. The person who blew you off all summer and is sniffing around again now that it’s winter

Dude, no. Have some self-respect!

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9. Your bartender

You can do this, but you’re going to have to find a new bar. Or at least memorize their shift schedule so you can still go. But this may have you drinking at noon on a Wednesday. Upside!

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10. Your roommate

We get the appeal of this. It’s seriously like having your favorite takeout every night. You don’t have to do any work because your date/booty call/soul mate is like... right there. And that, my friend, is exactly the attitude you can’t have, as this will quickly spiral into a sex-less relationship based on a mutual love for takeout. You will go right back to being roommates, except with deep-seeded passive aggression and resentment.

11. Your ex

Fool me once, shame on you. Fool me twice, seriously shame on me. You already know exactly what you’re getting into here, so we really don’t know how best to help you. The chances that this person has actually changed from the person you broke up with and swore you’d never speak to again are pretty slim. But if you insist that this time really is different, then just be smart about it. Be patient and treat this as if it is a new relationship and not the sequel to the old one. You’ll have to give breathing room for new mistakes. Don’t assume your ex is going to fail you again (even though they probably will). Don’t start freaking out about hypotheticals. You might be genuinely and pleasantly surprised when your ex comes through for you in ways they didn’t before. Just be cautiously optimistic and watch out for those giant, tablecloth-sized, frantically waving red flags.

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