Ow To Ask Out A Co-Worker This Valentine's Day

If you're thinking about asking out a co-worker – particularly with Valentine's Day approaching – the most important thing you can know is this: It's essential to proceed with caution because mixing work and romance has the potential to get awkward quickly.

Frankly, if you really want to play it safe, you're better off leaving work out of your dating life altogether. But the reality these days is that plenty of people do date, and even ultimately marry, co-workers. In many ways, that's not surprising. After all, we spend an enormous amount of time at work, and where else are you in such ongoing proximity to the same people over and over? When you work closely with people, it's human nature that you might end up romantically interested in one of them.

But asking out a co-worker can be tricky. Here are seven rules to abide by when you're navigating romantic interest in a colleague.

1. Do not ask out a colleague more than once. If you ask out a co-worker and you're turned down, you must stop there and respect their rejection. You get one shot, and one shot only. Otherwise you're getting into harassment territory – and creep territory, too.


2. If you get turned down, you must deal with it gracefully. That means no sulking or avoiding the person, and definitely no snapping at the person or penalizing him or her in any way for saying no. If you aren't confident in your ability to continue relating professionally and pleasantly to someone who rejected you, then you really shouldn't ask the person out at all. That is a clear sign that you aren't ready for workplace dating!

3. If you're interested in getting to know someone better, consider doing it in a group setting first. Rounding up a group of co-workers for a happy hour or Friday lunch and inviting your crush gives you a low-stakes way to get better acquainted and to get a better read on whether the person seems receptive to more contact.


4. Don't be a stalker. If it's taking you a while to work up the courage to ask someone out (which is fine!), resist any urge to do things like constantly find reasons to pass the person's desk, stare inappropriately, keep tabs on the person through a shared calendar or otherwise do things that are likely to creep out your colleague while he or she is just trying to work.

5. Never, ever ask out someone who's in your chain of command, in either direction. Your employer probably has a policy prohibiting this, but even if they don't, dating in your chain of command is a bad, bad idea. At best, it will give the appearance of bias and special treatment, and at worst it opens the door to abuses of power and even charges of harassment down the road. Even if nothing goes wrong, it will be terrible for your reputation.

6. Be aware of the risks if your crush says yes to a date. If you end up romantically involved with a co-worker, make sure that you're prepared for the downsides. For example, if you start spending a lot of time together outside of work, you may find it difficult to get away from your job and avoid talking about colleagues and work issues. It might also stymie your ambitions at your company, since you won't be able to accept any promotion that would have you managing someone you're romantically involved with. And if things end badly, you'll still have to see the person every day, which can make a breakup particularly hard. (These risks are especially pronounced if you work in a small office, where it can be particularly hard to get away from each other and where your relationship will probably be more visible to co-workers.)


7. Be choosy. You don't want to get a reputation as someone who sees the office as a hunting ground for dates, which means that you probably shouldn't use work for casual hookups. When you get involved with a co-worker, the risk of something going wrong and affecting you professionally is high enough that it's really only worth pursuing if you're interested in something more than a short-term fling. Otherwise, you're better off sparing everyone the potential hassle.


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