Lola Rolls
Advice on Life from a Former Sideshow Fat Lady

Dating at Work

Posted By on Thursday, February 27th, 2020

Dear Lola,

To be honest, I’m not sure a former sideshow fat lady is the best person to advise me, but I tried submitting my question to Carolyn Hax, and she didn’t publish it. There’s a guy at the office I’d like to date. We’re both at the same job level, so that’s not a problem. We would just have to report our relationship. Last week at happy hour, I mentioned to a friend that I was going to ask this guy out. She told me that I shouldn’t shit where I eat. That was a really gross way of putting it, and she was pretty drunk. Now, I’m wondering though, is she right?

–It’s No Picnic

Dear No Picnic,

I’m happy to answer your question, even if I am your second choice! (Definitely no hard feelings there, since Carolyn Hax is a very good advice giver.) In any event, I think your concern, like most people’s issues, has more to do with the universal complications of being a thinking and feeling person than it does with any specific circumstances.

Your friend, who may or may not be right, does nonetheless make a good point regardless of how inelegantly she expresses it. In an ideal world, you would find and interact with your romantic partner outside of the work setting. Unfortunately, while compartments are clean and easy, they don’t always align with what we want.

You don’t mention how much you know about this coworker, so, if you have not already done so, your first step should be to discretely verify his orientation and relationship status. Then, if he is an available candidate, think back over your interactions with him.

If you ask this colleague for a date, he may very well say no. How would that make you feel? Would you be embarrassed? Would this man be considerate of your feelings and professional reputation even if he does turn you down? Suppose you do go on to have a romantic relationship with him, what if that relationship ends or he breaks your heart? How would you feel having to see and work with him every single day?

Ask yourself these questions, as they can help you understand, but not eliminate, the inherent risks of putting yourself out there. Love is always a risky proposition. The good news, however, is that no one has ever died from embarrassment or from a broken heart. Consider, as best you can, what’s a stake and then decide if it’s work taking the chance. Also, write back please and let me know what happens.

Good luck!


Barbara Boehm Miller
Fiction Writer and Creator of the Character, Lola Rolls

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