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4 Questions to Ask Yourself Before You Date Your Co-Worker

Office romance may be a fact of the workplace, but is it right for you?
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Accidentally running into an ex-boyfriend can be awkward. Routinely running into an ex-boyfriend because he's also your co-worker can be straight-up torture.


Art Credit: Nima Salimi

“You should never date a guy you work with!” might be the conventional advice we hear from our moms and the HR department. Yet, as the veteran of not just one, but two, office romances, let me address a very apparent fact: Office dating happens. When you throw single men and women with similar interests in the same space on a day-to-day basis, you can hardly expect everyone to embrace perpetual platonic camaraderie.

Office couples have a lot of company. In survey conducted by CareerBuilder, nearly 40 percent of respondents confessed at least one office relationship during their career. More interestingly, the survey shows that Jim and Pam from The Office are not an anomaly in their relationship’s success. Compared to the typical dating odds, office romances have a larger chance of working out, with 31 percent of them leading to marriage. Power couples, such as Bill and Melinda Gates and Barack and Michelle Obama, are famous examples of work-sparked wedlock.

But what about that 69 percent of office romances that don’t work out? Clara, a 30-year-old designer, shared a story with me that sounds all too familiar:

“I watched a co-worker date another co-worker. Months later, they moved in together across the street from the office. They were always together. The relationship fizzled, they eventually broke up, and the entire office could feel the tension. Eventually she left the company and moved to a different city.”

Needless to say, while dating a co-worker definitely has its fair share of happy outcomes, take caution. You may not necessarily need to relocate if the relationship ends, but the stakes are still high in an office romance. Depending on the man and your own career ambitions, it might not be worth the potential risk.

It's a tough decision, but a quick gut check will go a long way toward helping you to make the best decision. Here are four questions you should ask yourself before you meet him at the bar for a one-on-one happy hour.

01. Can you trust him?

While trust is obviously an imperative foundation for any relationship, it’s especially crucial when your salaries are coming from the same place. Learning to trust someone is a slow, ongoing process, and isn't expected to happen over night. Still, there’s evidence that points to whether or not he’s the kind of guy who keeps his word—and one of them is your gut. If you don't feel comfortable simply trusting your instincts, here’s some questions you should ask yourself before you share intimate information with the office cutie: When he says something is going to happen, does it usually happen? Has he ever asked or assumed you would help him deceive someone? Does he ever withhold information in order to make things go smoothly or to avoid conflict?

These questions are good starting points when you’re trying to figure out if he’ll be spilling your personal details over donuts and coffee the next morning.

02. Does he confuse you?

I mean, really confuse you? While many of us are intrigued by a mystery man, mixed signals likely mean he doesn’t know what he wants, is immature, or is just playing with your emotions. Ask yourself the following questions: Does he shower you with compliments one moment and blatantly ignore you the next? Does he flirt with you... and maybe with that new intern, too? Are you the “friend” that he’s “hanging out” with all the time? Certainly, a little bit of confusion is to be expected when your romantic interest is sparked—and especially when you share colleagues and maybe a boss. But if you feel like it’s a constant game of hot-and-cold, and his intentions are dubious at best, back away. Who knows, maybe he’ll get his act together later, but it’s not worth getting involved with a guy who is putting you on edge.

03. Ask yourself honestly: Why are you even interested?

Let’s be frank: Crushing on a co-worker provides an emotional thrill. As a friend confessed to me, “It's fun. It gives you a reason to wake up early and primp in the morning, to wear your cutest outfit, style your hair, and put on pretty makeup. Then it's fun to make excuses to stop by his desk, flirt, smile, flutter your eyelashes, and break up the day. It's almost like being in high school again!”

Sure, dating should be fun, especially in the beginning. But ask yourself if you are attracted to the forbidden thrill of an office romance or the man who just so happens to be working 12 desks away? Would you still find him interesting if he wasn’t conveniently seated next to the snack machine? Typical office life isn’t without its dull days. Office flirtations are an easy way to create some distracting fun. Sometimes, they can even be advantageous to your career, giving you access to a greater network or experience level. And while those might be happy by-products of your relationship, make sure they’re not the reason you’re pursuing it—because in the end, it can seriously mar your reputation and ambitions.

04. Do you already know him as a friend?

You may like him for all the right reasons, but embarking on an office romance is one scenario when it might be best to let things simmer for a little longer than usual. Sure, there are ways to navigate around awkward office dynamics post-breakup but the best way is to foster a friendship first. You may want to give the romance a little more time to blossom before dating so you can decide if you like him enough to risk awkwardness at best—an emergency job change at worst.