Dear Anna,
About nine months ago, I ended a two-year relationship. We were deeply in love, but we found outside circumstances too much for our relationship to handle. A few months after the breakup, I met a woman at a bar. I was incredibly drunk and ended up making out with her the night we met. When I met her again in a more sober capacity, we went on a few dates and I found her to be a very sweet, cute girl who never stops talking. I intended to let her know (as nicely as possible) that while I did enjoy her company, I didn't see a future for us romantically. However, it was not so easy to get rid of her. She had an answer for every reason I came up with, and in the end I simply dropped the subject in order to spare her feelings.
With completely platonic intentions, I continued the friendship, knowing that she felt much more strongly about me than I felt about her. The problems began to arise when we would drink together and my inhibitions were lowered. We eventually slept together, which opened the door to us sleeping together several times. To be honest, I was still really hurting from my breakup, and it was nice to feel desired by this woman and it took my mind off of the pain of not having my ex anymore.
Fast forward six months, and I am finally ready to start pursuing a meaningful relationship with someone new. I have been on a couple of dating websites for about a month, and I have gone on dates with two different women. Nothing serious has happened yet, but I am hoping that it will soon. The problem is that this friend of mine is still holding out hope that we will end up together, even though I have told her many times that we will not.
I don't want to break her heart because I really do value her friendship. She is just not the one for me. Should I tell her that I am dating other people? Or should I end our friendship completely? I feel so guilty for leading her on and basically using her as an emotional security blanket. How can I let her down without hurting her too badly? — Selfish Jerk
Dear Selfish,
I think you're being too hard on yourself. You've told your rebound several times that you don't want to be with her. The fact that you slept together six months ago while you were recovering from your breakup is pretty irrelevant at this point.
Let's get one thing straight: You didn't "use" her. Consensual sex isn't transactional, there's no user and usee (?), especially since you were upfront with her about where you were emotionally. Was it the wisest choice to sleep with her after saying you wanted to be platonic? No, but we all make questionable decisions when grieving the loss of a relationship. Add drunkenness to the equation and those mistakes get magnified by 1,000. This probably won't absolve you from your guilt, but really, you're not a bad person. You're not leading her on.
There's no need to endlessly punish yourself. Forgiving yourself first and foremost should help you start the process of starting anew. Drunk sex happened, you've clarified your platonic position and now you've got to move on. You can do so, for starters, by telling your rebound that you're dating people. That's the kind of thing platonic friends share with each other. If she gets jealous or acts weird about it, then it would behoove you to "break up" with her again, using firmer language. Something like:
"Hey Rebound. I value your friendship, but I don't want to date you. If that's going to be a problem, then we shouldn't be friends."
Don't be wishy-washy or vague. Don't give her any kind of hope that someday you could change your mind or even that you'll have sex again. If she remains in denial or tries to argue with you again about your convictions, you should probably put the brakes on the friendship. Even if you do value her friendship, there's no point in trying to cultivate a platonic relationship with someone who wants something from you that you can't give. Plus, it'll continue to make you both feel bad about yourselves, which you don't need.
And don't hang onto the friendship out of guilt or pity — those are not the foundations from which trusting relationships are built. Experimental performance art pieces, yes; enterprising TikTok bakers/dancers/models/actors, yes; but not meaningful friendships.
So cut yourself some slack, be REAL with her (again) and if she's not down with it, then take a friendship break. She'll be better off in the long run, and so will you.
