1. A bartender. Any bartender, in fact, is a terrible idea. This has been clearly explained by our good friend (and eligible bachelor) Adam Fry. It won’t work out. You will be drunk 85% of the time. You will suffer from raging fits of jealousy and self-doubt. All you’ll really end up with is a lot of cheap bar tabs and possibly a STD.
2. Your friend’s ex. It doesn’t matter if they’ve been broken up for years. It doesn’t matter if they only dated for 32 days. It doesn’t matter if they split amicably. It doesn’t matter if your friend says it’s totally okay. It is NOT okay and it will be weird at every social function.
3. A family friend. You know Billy, the kid that used to eat paste in your living room when you were five years old that your parents have been trying to set you up with for well over a decade? DON’T DO IT. Your families will constantly be meddling and you’ll always sort of feel like you are dating your cousin.
4. A coworker. It is extraordinarily convenient to hook up a coworker. One too many drinks at the monthly work happy hour and you find yourself making out in a cab at the end of the night. You already know each other well enough that there is chemistry while there’s still a legitimate amount of mystery. It’s a trap! STOP IT! You’ll see each other for 40 hours per week at work and if it doesn’t work out, every second of which will be horribly awkward. You’ll have to switch jobs, end up working in a tiny cubicle next to a guy that cannot control his bodily noises.
5. Your boss. Same reasons as above except much worse. You will constantly worry that your coworkers know about your secret relationship with the head honcho. They will not only know but make comments behind your back. And god forbid you get a promotion during this torrid love affair. Keep your professional and personal life separate.
6. Your employee. Really? Do I have to explain why taking “Hey, intern, can you run and grab us coffee?” to “Hey, intern can you lay on top of me for 3-5 minutes?” is a bad idea? Come on.
7. Your personal trainer. You are paying your trainer to get you into shape so that you can feel better about yourself, meet new people, and look better than 60% of the people at Dewey on Labor Day. Yes, spending two-three hours together per week could translate into a friendship and possibly dating. Date your trainer at your own risk, canceling gym memberships can be a pain in the ass and you’ll likely never find another trainer that can take you from a 4 to a 7 in six weeks.
8. Your ex. So, you run into an ex at a party. You both look great. You’re both single. You have a couple drinks and the familiarity comes rushing back to you. Same jokes. Same chemistry. Same HORRIBLE REASONS THAT YOU BROKE UP. If it didn’t work out the first time, it won’t work out the second time.
9. Your roommate. You’re living in close quarters, you have one too many wine nights and hooking up turns into “let’s give this a shot, you know, for real.” No. Horrible. You have both signed a year lease. Do you know what a bitch it is to get out of one of those? You have to place Craigslist ads, interview new roommates, find a new place to live, and you’re so frantic that you settle for a new place in a shitty neighborhood with a small bathroom and a broken deadbolt.
10. Your neighbor. Same reason as above. Sure, you don’t live together, it’s not nearly as bad. However, you will still see this person in the morning when you’re out grabbing coffee, in the afternoon when you are walking your dog, in the evening when they’re bringing home someone better looking than you. And god forbid you have thin walls.
The list goes on and on, from married men (or women!) to your favorite barista (free coffee is not worth switching to a less convenient coffee shop), but what it really boils down to is you can’t choose who you are attracted to. You are going to want to rip your interns clothes off or have dinner and drinks with your personal trainer. It’s human nature. If you date one of these people, just be cautious and accept the fact that you might have to find a new job, switch gyms or possibly move across town.
- Suzie Robb