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Love in the Workplace

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Welcome to Karen’s Kicks a weekly column about the trials and tribulations of Love
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Hi Karen,

There’s this girl at work I really like. We’ve been working side by side for about a year now. She has a very busy social life and she’s always telling me about some bozo who broke her heart. She seems to have different boyfriend every month.

She often texts me at 4am with some sad break-up story and I try to comfort her. I think she likes me because we have so much in common and she tells me really personal stuff.

I’m 37 years old and I don’t want to play games anymore, I think she might be “the one”. She’s a few years younger 29….so…anyways…

we go for lunch a few times a week and once we went out to see a play together.
We’re never kissed or anything. I really like her and I want to tell her how I feel. What should I do? Would this be unprofessional?


Dear Tom,

It sounds like you have already established a great friendship. A year is a long time to know someone without any romance having been initiated by either of you. Have you ever considered that she may just want to be friends?
And then theres the question of – should you date someone at work? Well, my first instinct would be NO! However, if you were both unrelentingly drawn to each other, then you may want to consider another job in order to date, especially if this girl is your subordinate. A workplace romance can bring complications that you may not have planned on.

We often do not think these things through when we meet someone we are attracted to. If you proceed to mix your love life with your work life, you can put yourself under significant stress.
You also face the possible ruination of the friendship if things turn sour. If you date and then break up, how comfortable are you going to feel in the same workplace?

It’s complicated, it’s challenging, and it’s risky. If you are known to make good decisions; and if you cannot deny that “something” is there between you, proceed with caution. But, remember, it has to be mutual. Tell her how you feel. If it’s true love, it will be worth it and you will find a way to work through the challenges.

Good luck!