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in love at work

Published on February 21, 2011 by pinkglitter

For the past 2 years, I've really liked my boss. I'm leaving my job soon, and I'm contemplating saying something before I leave. All my interactions with him are very professional, not leaving much room for potential. I feel like he couldn't say anything due to the fact we're in a professional relationship, so I feel like the only hope is if I say something. We're both single. What should I do?


I think you should invite him out for a drink. The reason would be that you are leaving the job, you had fun here and that you would like to say goodbye to him in person. But maybe it would be more appropriate on you last day or so. And from that pont on, you'll see how it goes...but make sure to make some hints...look into his eyes and be flirty and sweet...good luck! xoxo

Your boss could have a lot to lose by suggesting anything personal while the two of you are working together; so the fact that you don't know that he is interested doesn't necessarily mean that he isn't. To start off on a good foot, you should let him do the asking. But that doesn't mean you can't make a subtle suggestion… something like "I hope we can still stay in touch after I leave" could be enough to let him know that you hope to hear from him, without really specifying the terms. If he has feelings for you, you'll hear from him.

Don't go there! You want a good reference on a professional level. If he is interested, he will contact you after you leave employment there. That is some dangerous ground, even after you leave. I would let it be unless he opens that door.