Q:

Gist of the issue is this: I went on a first date with a girl (I’ll call her Carly) I met a month earlier at pride and had a great time and great connection. We set up a second date, texted briefly about a couple things we talked about on the date and suddenly the next day she said she doesn’t wanna pursue anything anymore because she thinks I’m not over my past situationship that was with a best friend and that I am still friends with. As with all lesbian drama, it’s complicated.

Last year a very close friend of mine (I’ll call her Jane) realized she liked women and we had a 5/6 month whirlwind situationship (while she was still with her boyfriend of six years – I know I know stupid move). I just got out of an engagement a few months prior and the connection I felt with her and the way she made me feel wanted and not like a burden was intoxicating. While it was great in that sense, it was toxic as hell. We realized we’re just not good for each other and it’s best we stay friends.

This was a year ago. I had a very difficult time accepting that Jane wanted to end things and even harder time when she decided to get back with her boyfriend. She also never communicated, strung me along even after “ending” it and gaslit me about the fact that I was upset over us. I took the year to hurt and process it and also to try to re-establish my friendship with Jane. I started dating again a few months ago (May 2024). I’ve actually been meeting people out in the wild and not on the apps and have been enjoying dating again. Small aside, I never knew who I was or had any sense of self or confidence.

This past year I finally started dressing in a way that is comfortable and completely me, I’ve gained new found confidence, I like myself and know my worth. June 2024 I meet Carly out at Pride. My group kept running into her group and we finally all started talking and we eventually made out like crazy in the club. We exchanged numbers and went our separate ways. I ended up sleeping with Jane that night. It truly meant nothing. It was my birthday and pride, we were drunk and it had been a LONG time since I hooked up with anyone. Carly texted me and we had a little back and forth about pride and that was it. I genuinely didn’t think anything would come from it cuz we didn’t talk much or connect it was more a really good drunken make out.

A couple weeks later I decided to text Carly and ask her out because I just kept getting this physical feeling in my chest when I thought about her and was really drawn to her. We set up a date. Low key at a restaurant. The date ended up being 5 hours. After we ate we hung out in my car and just talked, and got touchy feely and then ended up making out like teenagers in my car for a good 20 mins. I’m talking windows fogged up everything. We had to stop ourselves from going any further. We also just talked and connected and I really really like her and who she is.

Now on the date, Jane was brought up because the day we met at pride Carly asked me and my friends if anyone was dating and Jane said no and I said not by my choice as a joke we all laughed. So that comment was brought up on the date when we’re talking about how we met. That naturally led to me explaining my situation with Jane a bit. We eventually came back to talking about Jane again when she asked about my most recent relationships. Idk if it was the smartest thing but I did say that I hooked up with Jane the night of pride. She later during the date was like I feel like you still have feelings for Jane. So I took the time to explain that I didn’t and that I’m truly past her and the toxic pattern I always fell into. I thought she believed it given that we made out after, had our hands all over each other as we talked and kissed good night. And then next day set up a date.

Carly then hit me with a text saying from what she gathered there’s unfinished business between me and Jane and she’s not comfortable with that and canceled the date and said have a nice summer. I told her that I don’t have feelings, I understand her concern but I’ve moved on, I thought we had an amazing connection and was excited to see where it was gonna go and to give me a chance to show her. She said because I slept with Jane she doesn’t really buy that I’m not over her. But she said she would like to take time and think about it. I was really sad to get that text and am honestly very frustrated and don’t know what to really do.

I feel like I’m now trying to convince her to wanna date me and that doesn’t feel great. I don’t know how to feel about her reaction. Just seems unfair to distrust my words and believe something based on assumptions about someone you just met. Is it worth it to bother with her?

I’m really genuinely upset and was very excited to get to know her. I also feel like this would be a recurring problem since I am good friends with Jane now and talk to her and my other best friend daily. There isn’t anything between us and there never will be given how she’s treated me (I told Carly that too). My gut says just wait and see and if she wants to give it a go then I will and see what happens and if she doesn’t, then obviously the decision is made for me. Would love to hear someone else’s perspective on this.

A:

Hey OP,

You’re right that like most lesbian drama, things get complicated fast. Histories intertwined, flowing emotions, good vibes that don’t make it to the runway for takeoff. Even a bit of Titanic car scene reenactment there. There’s much to untangle, but I think it eventually falls back to Carly’s perceptions and your feelings to it.

So I definitely understand the situationship you got into with Jane. Queer relationships often don’t take the shape or trajectory of cis-heterosexual ones. Most of us have — or know someone who has — gone through something that ill-befits the heteronormative relationship: two people, getting to know each other casually, then more seriously, then further.

It’s good that you see the emotional highs and lows that Jane brought into your life and were able to come out of it while keeping the friendship. Emotionally charged relationships often end explosively when the energy isn’t released carefully, but it seems you’ve found your way back to a satisfactory default. One where Jane is a presence in your life, but in a way that’s not detrimental to your desire to keep exploring.

And explore you have! I adore the energy you found with Carly. The first thing I saw in your story about Carly was the emotional intensity you felt in those encounters. Even without the info about your efforts to keep connecting, it’s clear that this meant more to you than ‘just’ making out and petting. I’ve been in that position quite a few times — making out, rubbing, touching, dates going very well. My emotions and hopes are buoyed, and I develop a daily grin that is hard to dispel.

And then the other person disengages.

That plunge from hopes to reality is always worse the more intensely we feel about the other person. I want to say you’re ‘lucky’ that Carly gave you a rationale before her departure, rather than just vanishing. But getting a rationale can just invite a new wave of what-ifs and maybes that eat us alive. In the end, the situation you were dealt is now the one you have to manage and recover from.

My first Big Thought to come out of this situation was that perhaps Carly just has a different boundary line for a person’s ‘closeness’ to their exes. I recently answered an AF+ Advice question where the asker was trying to explain to their partner that they’re still sharing a bed with their ex for financial and logistical reasons. I think you’re facing a similar rift in opinions: Carly sees something between you and Jane, and she believes her version, whether or not you think it’s true.

I think your ‘not by choice’ remark about not dating Jane factored into Carly’s conclusion. I don’t hold it against you for cracking a joke like that, especially at a Pride event where things are… loosey-goosey and celebratory. I don’t think it was wrong to say, but it may have affected Carly’s opinion of the situation. An opinion that was probably reinforced in your car conversation about Jane.

I could elaborate and elucidate and whatever all day about Carly’s thought processes, but what I’m going to say is this: She has an opinion, and that’s going to suck for your goal of being with her. The people we pursue are allowed to be wrong, even utterly wrong in our eyes, but they’re still allowed to use that as a rationale to make decisions. If they follow that line of thinking to its conclusion, it’s really their loss for losing out on us. This would be hard for me to hear, but I think it applies: Carly’s current opinion is contrary to your desires and it’s probably not even your fault, but it’s already happening.

So, to actually answer your question of is it worth it to bother with her and the attending issues about feeling like you were not trusted…

I think that at most, you can give her the requisite time to think and maybe arrange another meetup to talk over the issue. But positioning this situation as a key discussion point so that if there are any other distractions, it doesn’t detract from actually resolving this conflict. If she asserts her desire to exit (in text or otherwise), then we’ll have to respect that. As it stands, I’m willing to trust in Carly that she needs time to consider this, and if I were you, I’d also use the time to think about your interactions with her, Jane, and how you fit into them. Just to see if there are any blind spots you’ve missed.

I don’t think it was fair on you to not trust your version of events. If you erred in how you presented that story, maybe it would have been fairer to give you a chance to clarify the situation. For now, I’d give Carly the space she’s asked for and after an appropriate amount of time, ask for another opportunity to talk about it. Her answer then will tell you what you need to know.

No matter what, this is rough footing for starting a relationship. It may turn into the uphill endeavor of, as you say, trying to convince her to wanna date me. That’s frustrating, even when it’s caused by an honest misunderstanding. Despite these pains that I also feel keenly, I’m actually rather… proud of both of you. Carly has communicated her interests, opinions, and desire for space clearly to you. You’ve been upfront with us (and Carly) about your past with Jane and how you experience relationships. And you’ve clearly done a lot of thinking about it. That all deserves credit, even if things aren’t panning out as you’d like.

For now, I think it’s best to give Carly and yourself some time to settle before taking the next step. It’s enjoyable to be taken in by a new and exciting person, but that intoxication is often joined with an unpleasant hangover or morning realization. You’re in that place now, and it might be helpful to take each step as it comes. Be assured that tomorrow will still happen, whether Carly is present in your tomorrow or not.

You can chime in with your advice in the comments and submit your own questions any time.

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