Thoughts on dating (or at least hooking up) with a coworker? I spend most of my waking hours at the office, and there is one other gay guy I work with. We spend at least 40 hours a week together. We flirt when no one else is around. Should I pull the trigger and ask him out for a drink or something?

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If you don’t have any line of reporting into each other or any responsibility over one another’s work, try it. If he says no, you need to likely cool it on the flirting so there’s no misconstrued lines of sexual or implied harassment.

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Don’t do it. It will likely go bad in the end (most relationships or other situations do) and ultimately make working together awkward or worse.

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Just don’t. What if it doesn’t work out? It will be impossible to work together after that.

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I have a hard and fast rule that I do not shit where I eat.

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Why not. Maybe ask him for lunch first just to see if there’s any interest. Or just ask him if he’d like to grab a drink. There’s no harm in that. I’ve always been very leery of workplace dating though.

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Do it and let us know how it goes. Good luck!

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Both of you can get buzzed, not drunk, at a work happy hour to see how you both feel when your inhibitions are down. I 95% agree with everybody else about avoiding relationships with coworkers, especially when the honeymoon phase ends and you realize how much you are around eachother. The other 5% is missing out if/when a feeling is insanely strong. My definition of insanely strong includes dreaming about this person, this person being the last person you think about before falling asleep and/or being the first person you think about when your eyes open in the morning. Do you find yourself acting any different around this person? If so, I say tread lightly as long as you are treading!!!

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You spend 40 hours a week working together??? That is too close for comfort. Any relationship problems would surely spill over into work, and one of you would need to get a new job.

Don't move forward with any attempt at a relationship or even friendship outside of work until there is much more professional distance.

You should do it! However, make sure you somehow document that “whatever happens” is consensual and mutual

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