Playing For Real

Dear J & J: A female coworker and I started telling people at work that we are an item. We flirt with each other when people are around, and sometimes when they aren’t. The problem is that lately I have found out that I actually do like her. Should I tell her the way I feel? If so, how do I go about doing so? The thing is, I do not want to lose her friendship.

J.M.C.
Tucson, AZ

JACK: Rather than announcing your love on the company paging system, try taking your "camaraderie" outside and after work. If you are already friends, simply suggest a meal or a similarly non-threatening activity outside of work. If your instinct is correct, your relationship will develop naturally.

JILL: Your question is less about dating a coworker (a can of worms in itself; for more info on this, please see More on the Fine Lines of Whom You Can Date at Work and than it is about changing the nature of a friendship. Clearly, if your friend was amenable to "play dating" she has some level of attraction for you. Whether that attraction is the platonic or romantic kind is yet unknown. I would follow Jack’s advice but take the whole thing really slowly. In fact, I would hold off on any admissions of love altogether. Instead, hang out outside of the workplace and see what develops. If there’s romance there, it will happen. If nothing ever does, consider setting your sights on someone off of your bread-and-butter plate.

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