Your Call: Should You Make a Move on Your Roommate, Who’s Also Your Best Friend’s Sister?

photo by adactio

Dear Em & Lo,

My issue is that I fantasize about sleeping with my best friend’s sister — I have for several years now. I feel I’m a little obsessed about her. She has a boyfriend. The worst part: we share a flat together. Fortunately, she’s out a lot, and when she is around I do try to avoid her. Do you think my desires toward her are unhealthy? Are they just a result of proximity? I currently don’t have a girlfriend but even when I did, I thought about her. It’s a tough situation and I’m not sure what to do, if anything?

–Single Whipped Male

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  1. Yup. What Rei said.

    Really, there are only two things to consider: Whether the fact that she has a boyfriend means anything to you, and whether continuing to live with her AND your feelings towards her will be okay for you.

    I see that this is difficult and there are lots of things to consider (how long will she keep that boyfriend? If they break up, who will break up? How long to wait after that? What will your best friend say? What if she doesn’t like you back? What if she does? What if it doesn’t work? What if things get really awkward? and so on). But just considering 90% of the possibilities, moving out rather sooner than later should be the easiest for you. Good luck!

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