Office Romance: Yes or No to Dating a Co-Worker?

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Dating a co-worker

When I started a new job a few months ago, my main concern wasn’t trying to fit in with the corporate culture, impressing my bosses or figuring out how to become as proficient as possible. All I cared about was asking the cute, blue-eyed girl in the center cube out on a date.

Each morning I’d strategize the best way to ask her out, only to wuss out. Since I was the “new guy” and barely knew her, I didn’t have the balls to just walk over to her in front of our co-workers and ask her to hang out. So, I ripped off a scene from Wedding Crashers and left a post-it on the blue-eyed beauty’s desk one night after she and her cube-mates left. The post-it read: Drinks after work tomorrow? Yes, No, Maybe – with a box next to each potential answer.

Post-itUnfortunately, Blue-eyes’ first reaction to my childish attempt at flirting, as overheard by my friend who sits near her: “Is this a prank?”

After considering the best way to play this out, I finally just went over to her desk and told her I left the post-it. She smiled and told me she didn’t take the note seriously, at first. But I did, and I asked her to respond and return it to cube #177, as per the instructions. So just before the five o’clock exodus, she came by and told me she couldn’t hang out that night, but suggested that “we should all do drinks sometime.” Well, after just one drunken night out with her and the rest of the gang, I got the old, “Nice try, Slugger, maybe next time” and decided to give up the chase. Now it’s only minimally awkward when we pass each other in the hall.

Read How to Hit on a Guy

But the awkwardness I feel whenever I see Blue-eyes these days is nothing compared to the bizarre situation my co-worker, Matthew, 26, found himself in. Matthew is currently dating a girl he works with (let’s call her “Ellen”). But before that, he dated a different girl from the office (“Lauren”), who we all still work with, as well. Matthew hooked up with Lauren two years before I started working at the agency and she was his dream girl, except for one minor problem: She had a boyfriend.

“I hung out with her a lot,” says Matthew. “We had lunch together every day and we used to hang out after work a couple nights a week. I finally told her how I felt after we went to a Giants game together.”

Lauren responded by telling Matthew their time together “felt like a dream,” but she already had a boyfriend she wasn’t willing to part with. A few days later, for her birthday, Matthew gave her a CD with a song he dedicated to her. “After that, things got pretty weird,” he says. “She stopped talking to me, even though I told her I wasn’t expecting anything. I gave her the CD for closure more than anything else.”

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26 thoughts on “Office Romance: Yes or No to Dating a Co-Worker?

  1. Hmmm… I dated my co-worker when I worked at a bar, and although we didn’t tell anyone at first, it was so awkward. My other co-workers would say things like “You guys would be so cute together,” or “he’s flirting with you,” blah, blah, blah. It just made things weird, but it happens a lot in bars. I worked at a different one, and EVERYONE there was dating each other… the bar backs were dating the bartenders, bartenders were dating the cocktail waitresses, boss was dating the hostess. It was crazy.

  2. I do know someone who got married to the coworker she started dating in secret, but that’s the exception. Most of the workplace romances I know did NOT work out.

  3. I’d definitely think twice before doing it (and wouldn’t want to hook up with someone I worked directly with), but “Grandma” has a point — you really DO get to know people much better when you spend time with them day-in and day-out…

  4. …well sometimes I guess you just can’t help it & thing just happen. I guess as long as their is no problem between both parties once the relationship is over it should be ok. ..that is unless there are strict policies. then your just screwed!! lol!

  5. Keep your work and personal life separate; if professionalism is kept at work and individuals are treated the same way despite their favoring towards each other, I really don’t see a problem. I work with my boy at times when shifts needs to get covered and it never is a problem. Put your head into the game and act your age- PROFESSIONAL 😉

  6. I don’t think it’s a good idea…it will become “everyone’s business” and make for water cooler discussions. But, the post-it idea was cute!

  7. There are so many really nice guys where I work but most of them are married or too young. One of my mangers told me we should go to happy hour together (total babe) but he’s married with three kids yikers!! What’s a single girl to do 🙂


  9. I have a question in regards to making my move on someone at work. I’ve had a crush on a guy at work for awhile and initially thought he liked me too, but quickly gave up hope. However, I was recently told by another co-worker that he does have feelings for me. His birthday is in about a month and I thought it would be cute if I got him a small inexpensive gift and left it on his desk. Should I leave a little note as well and, if so what should it say?


  10. Hi,On the off chance that you are into an office romance,you may need to keep it secret at first.Some secrecy dependably helps in light of the fact that on the off chance that you see that the co-worker you are dating is not the best match you can have,then it is times better when not everyone around thinks about it.When you have dated for some time and you see that the things will work,you can report your affair yet and still,at the end of the day bear in mind that your office is not a private boudoir and dodge public display of affections.Kissing and hugging before your colleagues is absolutely not what a true professional will do!Thank you.

    @Amie Stark.

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