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I Think My Boss Has a Crush on Me…

Dear War Virgin,

I think my boss has a huge crush on me.  He often keeps me late after work, well after everyone else has gone home.  Plus I never know when he plans on keeping me around until right before the end of the work day.  I think my work is done, but then he comes up with what seems like a bogus assignment.  I say it seems bogus, because then he ends up chit-chatting with me for a long time, as if the work wasn’t important.  This is starting to make me very uncomfortable, and it’s also interfering with my free time to a point that’s making me very angry.  Is there anything I can do?

-Samantha, 25, Tacoma


Dear Samantha,

The easiest way to take back your free time is to have previously scheduled appointments set up for your evenings.  Since you’re young, and I’m assuming without children, your boss probably feels that he can monopolize your time.  If you’ve never pushed back and told him that you had to leave for an appointment when he made you stay late, then you’ve established a precedent of being too accommodating.  But don’t be upset with yourself for doing this.  You’re young and new to navigating the difficulties and politics of the work place.  Shame on him for taking advantage of you!

If you don’t want to confront your boss head on about him not respecting your free time, which is probably the prudent thing to do, then in a casual, friendly way, tell your boss that you’re taking up a new activity.  Hell, you can even make one up if you don’t feel like doing anything in the evenings except  watch T.V. in your PJs.  I recommend doing this in a planning meeting, when you’re both discussing a project schedule, etc.  You can say something to the extent of, “By the way, I just wanted to let you know that I’ve taken up kick boxing.  It meets 3 times a week at 6 PM.  You’re ok with me leaving work on time to do this, right?”  Hopefully he’s cheerful and agreeable to this.  If not, then you can assure him that you will reserve one evening a week to staying late and being available for last minute work emergencies.

If your boss refuses to accept this, or if he causes some more subtle, passive-aggressive backlashes, then you have a more serious problem on your hands.  Then you need to decide if you want to speak with someone in your HR department, or if your company doesn’t have one, then with his boss.  If this is the route you choose, then instead of coming out and saying that you think your boss has a crush on you, simply state the facts: “My boss won’t allow me to attend evening gym classes, because he says that he needs me to work late.  I would like assistance in finding a reasonable alternative.”

Or you can lie and say you’re starting graduate school classes in the evenings.  I actually started a MBA program in the evenings, and it forced my pain-in-the-ass boss to leave me alone and grant me a lot more free time!

About the author

Laura Westley, aka, the War Virgin, hails from New Port Richey, Florida and graduated from West Point in 2001 with a degree in Chemistry and a minor in Nuclear Engineering. She commissioned as an officer in the US Army Adjutant’s General Corps and was assigned to the Aviation Brigade, 3rd Infantry Division in Savannah, Georgia. On March 21, 2003, Laura and her unit were a part of the initial Iraq invasion.