DEAR SOMEONE ELSE’S MOM: My friend “Austin” and I keep finding ourselves attracted to the same person. Austin is not at all shy and will start talking with whoever he is attracted to, and I always back off, even if I like the other person for more than hooking up, which is usually all Austin’s looking for anyway.
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There was this one girl, “Lily,” who I really liked, and she seemed to like me too. I was getting to the point of asking her out, and before I had my confidence in the right place, Austin got to her, dumped her, and I have barely seen her since.
That becomes another problem, even after Austin is no longer interested, he always leaves the girls he dumps hurt and not wanting anything to do with him, which means they don’t want anything to do with me because I am his friend.
A few days ago I ran into Lily with some friends. She was polite and all that, but I think because she was with friends she didn’t want to spend too much time talking to me. But for the first time since she and Austin broke up, I had a feeling she might not hate my guts too.
I want to reach out to her again to see if there’s something there, but I am worried Austin will become an issue. Do I tell him I’m going to try to see if Lily is interested in me, do I just go ahead and not say anything to Austin for now, or do I just let it all go? --- IS IT MY TURN TO WIN?
DEAR IS IT MY TURN TO WIN?: For the sake of being above-board with your friend, it’s not a bad idea to let Austin know your plans. However, you don’t need and should not seek his approval.
Lily is her own person, and hopefully able to make her own decisions about who she spends time with. You ought to feel the same way about yourself, regardless of your friendship with Austin. You’re not looking to compete with him for a woman he ditched. You’re hoping for a chance to pick up where you left off with Lily before she and Austin were together.