DEAR HARRIETTE: There’s this guy I’ve been interested in for a while now. We have great chemistry, and every time we hang out, I find myself liking him more. The problem is, he’s already gone after three of my friends. Each time, he’s flirted with one of them or dated them briefly, and even though none of those relationships turned serious, it’s left me feeling conflicted. It makes me feel embarrassed and kind of foolish for still being interested in him, knowing he’s been involved with my friends.
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I can’t shake the feeling that there’s something between us, but at the same time, I’m worried about what it says about him -- and about me! -- if I pursue something. Part of me feels like I should just move on and let it go, but then I wonder if I’m overthinking it. I don’t know if I’m putting too much weight on the fact that he’s dated my friends, or if it’s a red flag I should take seriously. How do I get past the embarrassment I’m feeling? Should I be concerned about his past with my friends, or should I just focus on my own feelings and see where things go? -- Too Close for Comfort
DEAR TOO CLOSE FOR COMFORT: How close are you to the friends he has dated? Seems to me you might ask one of them what happened when they dated. If you feel comfortable, reveal that you have liked him for a while and you want to see if there’s any chance for the two of you, but you are apprehensive given that you have noticed that he has dated people in your friend group. Yes, you risk not keeping your feelings a secret, but it could be worth it to find out any details about how this guy behaves when dating others.
Pay attention to the feedback you get. If you do decide to pursue him, you can also ask him -- when the time is right -- what didn’t work when he dated other women you know. But that’s for later.