How To Romance In Office : Dating With Co-Worker?

You all loved this article on whether or not you should date a co-worker.

 It's getting chilly and you may want to just look across 

the conference table for someone to snuggle with.

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. 

Yes, No, Maybe – with a box next to each potential answer.

Unfortunately, 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.

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.”

Unfortunately, there wasn’t much “closure” for Matthew, 

as Lauren’s seat got moved to the one next to him.

 “For awhile, work was terrible,” he says. “It was difficult

 to function. It’s really hard to move on from something when

 it’s thrown in your face eight hours a day.” Matthew eventually

 got past the drama with Lauren and began seeing his current

 girlfriend, Ellen – who, at least, sits on the other side of the office.

“It’s easier to meet people at work because expectations are lower,

 at least in terms of dating,” says Matthew. “You just have to be

 careful who you talk to, I’ve learned. It’s definitely important 

to keep your private life private.”

This theory makes sense when you consider the number of hours

 worked per week versus the actual time one spends going out.

 I normally don’t leave my apartment until after midnight on

 Saturday, which means my total time to mingle and meet

 women is less than four hours, when you factor in New York 

City’s last call. (Thank God I’m no longer in Boston, 

where everything closes at 2 a.m.!)

At least in the office there’s time for the relationship to 

grow organically, rather than having to rely on a 15-second

 drunken introduction at 3 a.m. (Besides, my grandma always

 said that the best way to know someone is to live with them

 or work with them, because their true colors are

 bound to come out eventually.)

On the flip side, if a girl at a bar flat-out rejects me, my bosses and 

co-workers aren’t going to know all about it. (Unless, of course,

 I write about and share my failures with the world.) 

But if a girl I work with turns me down, it’s going to become

 all the rage around the old water cooler because, honestly,

 work is boring and gossip is exciting.

After experiencing two relationships in the same office,

 Matthew knows all about these highs and lows. “Work can be

 a great place for a relationship or an awful place,” he says. 

“If it’s going well, it’s great because you see them all the time.

 If it’s going poorly, it’s awful because you see them all the time.”

OK, he may have a point, but if I’ve learned anything from

 Matthew’s experiences dating co-workers, it would be

 “if at first you don’t succeed, try again until you do,”

 especially if there’s a really cute brown-eyed girl on the

 other side of the office who catches your eye....

Wish me luck.

Tell us: Have you ever dated a co-worker? What happened?