Ask a Girl: When Is It Appropriate To Ask Out A Co-Worker?

Our friends over at StyleList want to help you out. So, instead of just assuming you know everything a woman desires, why don’t you listen to the editors at the premiere fashion site on the Web and make sure you are doing the right thing when it comes to the opposite sex. This week: inter-office dating.

We took to the work place to answer this one, and polled the ladies around us for their thoughts on inter-office dating. As expected, responses were mixed, but most of all, answered with a bit of hesitation.

While a few girls instantly answered with a resounding “absolutely, positively, 100% never,” the rest seemed quite open to the idea of fraternization. Don’t get any ideas, though – we still have our rules! If you’re planning on taking the plunge and asking out a fellow employee, follow these guidelines to ensure success, minimize rejection, and alleviate post-drunken-hookup-guilt….is that even a thing for guys?!

1.) Get Real with Yourself – do you just want a hook-up, or do you want to go out on a real, live date with this person outside of your apartment? If you’re just trolling for a convenient booty call, spare everyone the hassle.

2.) Date Outside Your Team – it’s dicey enough to date within your office, but within your own team can be even trickier. It can put you, and the girl, in a bad situation with coworkers and your boss. A surefire way to rejection is compromising a girl’s image with her peers. Set your sights on someone who you don’t have to see in your daily meetings. Every. Single. Morning.

3.) Cast The Lines – Be absolutely positive this chick is into you. Almost every girl we asked who said she would be open to scoping out the office dating scene said they would hate to be caught off guard by someone they were totally disinterested in. If you just go for it without putting the feelers out first, you instantly go from being a potential Jim Halpert to a Michael Scott (and if you are a Jim Halpert, please call us).

4.) Keurig Is The New Water Cooler – Work the coffee machine and break room. Strike up a conversation over morning caffeine cravings. Ask her about her weekend or make a joke about the annoying company memo that just went out. Friendly and light conversation is a great way to take a slow and steady approach to asking someone out. It’s also a great way to find out if she’s seeing anyone special. “So, did you watch the Grammys with your husband last night?” – “Oh, no, I’m not married.”

5.) Secret Admirer – Suitors from afar are pretty much exactly what they sound like – straight up not cool. Anonymous love notes and longing glances from across the copy machine may seem like great ideas at the time, but the execution just never really pans out. It’s creepy and draws way too much attention in the office. Stay traditional and make your moves face-to-face.

Well guys, there you have it. If this guide to office fraternization doesn’t help you, we’re not really sure what else will. If all else fails, rent Fatal Attraction – we guarantee you’ll never think about dating that girl in the cube next to you ever, ever again.