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Crossing Boundaries with Friends and then Trying to go Back

Dear Shay,
Before I start, wanted to say that I love your column. Its a great source thats entertaining and informative. Now onto the crux of the issue. I have a friend whom I met at college. One night we were hanging out and (after too many shots of whiskey) we start making out on the couch. The next day I felt that because we were too far apart in age (she’s 7 years older) and because I wasn’t ready for an emotional or physical relationship at that time, that I should not continue to see her in a romantic way. I told the next time I saw her and she agreed that we shouldn’t be dating but that we should continue to be friends.
Now, several weeks after that event has occured, she messages me every day now with how her day is going and that she wants to hang (again all the time). Also whenever I do see her she flirts with me more and more, such as touching my shoulders, my neck, and kissing my cheek. I’m fine being her friend and hanging out with her but is there any way to make her see that I don’t want to be anything more? I feel that she wants more than i’m willing to give but I don’t want to hurt her or make her feel embarrassed.
What is a little worse is that now there is a girl in my class that I really do want to ask out but I don’t because it might hurt my friends feelings. I believe she hasn’t had many bf’s before this and me rejecting her after kissing her would hurt her self esteem. What are your thoughts on this and is there any way to continue a new relationship without hurting my friend?

It sucks when things get out of hand and you do something that you know you shouldn’t with a friend.  Crossing boundaries can be wonderful, but it can also be problematic and it affects people in different ways.

Since you’ve already talked to her about staying friends but not going any further romantically, I think you should try ignoring her advances (for now) and continue to treat her like a friend.  I text my friends all the time and I like to hang out with my friends – however, I don’t (usually) rub my friends’ shoulders and necks or try to kiss them on the cheek.  And this is the behaviour that seems to be the main problem because it shows that she feels a little more than friendly towards you.  Since you don’t want to hurt her feelings, you’re going to have to be subtle – you’re also going to have to accept that whatever you do, you probably are going to hurt her feelings,  at least a little.

Talk to her about this girl that you’re interested in, ask her for advice, remind her how glad you are to have her as a friend. These are subtle ways to hint that you care about her, but that your feelings towards her are platonic.  This will also let her know, gently, that you are interested in another woman.

If she doesn’t seem to take the hint, then you’ll have to talk to her about how you’re not interested in her in that way. It may end your friendship, but hopefully not forever.danbooru_unf-p-114688894661280

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