Succeeding at Dating a Co-Worker

‘He was devastated — way more than I thought he would be, since we’d only been ‘dating’ for a few weeks.’

“I once had a coworker — I’ll call him ‘T’ — who had been flirtatious at the office holiday party and afterward, but I didn’t think anything of it.

One day T asked me out to dinner at a fancy French restaurant, which should have been the moment when I caught on, but I was still completely oblivious as to his intentions. I assumed we were hanging out as friends.

“After dinner, we stood outside the restaurant talking, when T made those intentions clear by swooping in and kissing me.

“For the next two weeks or so, we went out to dinner and the movies a few times, though we acted as usual at work and absolutely no one knew. I felt a little weird about it because, A, it was a super-small company, and, B, I didn’t know how much I really liked him.

“Eventually, I realized those two factors combined did not make for the beginning of a great relationship, so I told T it was over. He was devastated — way more than I thought he would be, since we’d only been ‘dating’ for a few weeks.

“A few weeks later, I left the company for a different job, which had nothing whatsoever to do with us dating. T kept trying to rekindle the relationship, but I told him (as nicely as possible) I wasn’t interested. I haven’t spoken to him in years, but I know he’s still at our old company. I’m dating someone else now, and I assume he is, too!” —anonymous Business Insider reporter

‘That got a few people giggling and us blushing.’

“My girlfriend and I met seven years ago while working at a national consumer magazine in New York City.

“She was a graphic designer and I was a copy editor, and under the pretense that I had queries about kerning in cover lines, I’d knock on her office door in hopes of luring her out for a drink. After a couple of tries it worked, and the rest is history.

“But even after we started dating, we tried to keep it on the down low. While some friends at work knew about us, through gossip and after-work drinks, most of the staff didn’t know or didn’t care.

“One time, though, during a big edit meeting, the managing editor was going through her list of all those with upcoming vacations, and it so happened that my girlfriend and I were taking the exact same days off (for a trip to Mexico). That got a few people giggling and us blushing.

“Neither of us had ever dated a coworker before that — we were both a little wary of it — but I’m happy to say it worked out.” —Daniel McMahon, Business Insider copy chief

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Succeeding at Dating a Co-Worker

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