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I feel like a fool even asking here...
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I'm sorry in advance that this is long - it's part vent part solicitation for advice...I have tried to be succinct, I promise.

Been seeing a woman since early September. Things got physical early (consenting adults and all) and her response to that in the moment freaked me out (crying as I climaxed as she felt she was cheating on her ex she hates). It was triggering as hell for me, and I freaked out. We ended things romantically, but stayed FWBs with the understanding we would date other people and if things got physical we would notify the other person.

We hooked up once more, but as two single parents with limited childcare that was mostly it. We texted one another for over a month after. She went on a few dates with other people that didn't click. During this time, I had developed some feelings. I thought I'd been rash in ending things, and I was genuinely enjoying talking to this woman every day. She told me about a guy she was dating one day when things were failing - guess the guy has a rap sheet, after a few weeks was talking about kids and even adopting her son. Crazy shit. Figuring that was coming to an end, I apologized for having ended things before and that I was into her, and explained what had happened. She said she was into me as well, and she was going to dump this guy (or had already). We keep texting, and she goes on another date with him and they end up fucking. I was disappointed, as I thought she was ending things/had ended things with him, but also it was on me for making things complicated figuring my own shit out. I told her I wasn't going to compete, didn't want to get in between her and someone she was dating, and left it at that. I went no contact for a while.

She calls me one night two weeks later. She ended things with him, said she missed me. Going through a lot right now at home, and was unsure she wanted to do anything serious. I suggested we just casually date exclusively - no worries about multiple partners, no formal bf/gf titles - just get to know one another better and hang out where possible. Things were going pretty well I thought - I took her out to dinner one night (matching nights off are challenging so I called in a babysitting favor), and we would sync Netflix together and talk on the phone watching a show she loved and was getting me into. She told me she was still talking to the other person - even though he wasn't right for her, she was going to cut things off, it was just hard. I wasn't going to force her to do that - I told her I didn't care who she spoke with, but going out with him would be my line in the sand.

It happened last Saturday - she went to a Christmas party, then out to a bar and he called - so she invited him out. We were supposed to see each other the next day, but she left her phone in his car and I couldn't get a hold of her that morning to confirm. She told me about inviting him out, apologized, a bunch of stuff about her being broken, etc. I was hurt, mostly because I felt so...worthless. Like, this dude who you've stopped talking to multiple times was worth sacrificing something good we had going? I guess it was the twentieth anniversary of his mother's passing hence the call / invite...but ironically enough, that was also the anniversary of my losing my sister to cancer so it just hit harder. I was hurt, and I was done.

Today, another apology text. Wants to talk but understands if I don't. Tells me she unequivocally told the other guy she's done. Wants something normal and healthy but isn't sure she is capable of that. I feel bad - because I know how that feels. I genuinely want to be her friend, but now there's also feelings. I don't want to dive into anything serious but I liked the trajectory before - slow, casual, but it felt like I was building something with her. I suggested going back to that - that I wanted to still explore a relationship with her, still be a friend, be supportive - that maybe it might be easier to sort through things if you have the support of someone who cares about you, rather than to seek validation from strangers. We chatted a bit more, and towards the end of the night I wanted some clarity so I asked what specifically she wanted - "I want to take things slow and casual right now, at least until (early next year). I need a friend more than a partner right now, totally get if you aren't feeling that".

To this, I said I could be a friend but I'd need time. She asked why, and I said because there's feelings there and I didn't want to keep bouncing back and forth. She went to bed after that.

I feel like such a fool. After all that, and then today after being hurt considering let's put this in the past and just figure out stuff say by day and thinking we were on the same page and then just...i need a friend. It gives me vivid memories of being friends with girls in high school, being a sounding board, and then being dropped as soon as they feel better or have someone's attention. I'm almost 40 and I spent 17 years in a toxic, abusive, loveless marriage and sometimes it's hard to reconcile if that was worse or if dating is - especially since I have so little experience. It's a nightmare even getting a match on a dating app, and then from there actually having a conversation - let alone jumping to a first date.

This is the first person I've felt anything for in years - and I know the above is probably the equivalent of skiing into every red flag on the slalom course. I'm trying to be a supportive person and forgive people for their flaws, but I don't want to be taken advantage of again. I want to be there for this person I've developed feelings for and don't want to go back on what I've said about being a friend to her - but I'm also trying to grow as an individual and set boundaries, so I don't end up in a situation like I did before.

Whats your take on this, reddit? Am I being really stupid here? Any advice in general?

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9 months ago