I'm (28 M) recently back to dating after my only long term relationship, which ended very badly last year; I have very little experience dating in general, and in retrospect I think I got in a relationship with my long term ex because we just both were not quite "right" mentally and emotionally.
I managed to actually chat online with a woman after a few months of zero success in finding anyone to show some interest back. I tried my best not to get ahead of myself, and I think I did better than in my younger years, but I still was emotionally invested since I feel I have so little options.
We met for a first date, walked and chatted, had a non alcoholic drink… I thought things were going alright, conversation was flowing for the most part, and I initiated some touches here and there (shoulder or back, mainly to show which direction to take while walking), we both were smiling and chuckling from time to time. Then a few plans went bust since a lot of things are closed down from the pandemic, we hopped to a first place than another one and then went to grab a bite in an awkward spot (not much left on display, very few seats allowed). I sat next to her rather than opposite. I tried to get the conversation more playful, and I scaled up the contact, grabbing her hip a few times, I figured if she wanted to sit down and eat she had not rejected me yet so things were progressing. Conversation went as we ate the food. I displaced her hair to show my intent on kissing soon. We were done eating at that point, so I figured she would say we should leave if she was not feeling it. I went for a kiss, which she rejected with a simple "no" and awkward smile, and I kept smiling and said "that's fine" and got the conversation going again as best as I could in order to not dwell on that awkward moment.
Then she suggested going to a shop for her to buy something, again I thought she was still open at that point otherwise we could have just called it a day here and there. We went there, chatted a bit, and I stopped with the physical contact since I feel I had already clearly overstep her boundaries very recently.
I was a bit lost and trying to think of the next move, but in retrospect I should have called it a day, because she quickly said she was going home. She stood there awkwardly smiling, I was smiling too, I told her it was nice meeting her, she replied the same, I went for a friendly hug which she did not "participate" in, then went off.
I ran some errands and went home which took about an hour and a half. Very confused, I sent her a text telling her I had a good time, mentioned something that made us chuckle during the date, and wished her fun for her plans tonight. She texted back about two hours later, apologizing for the delay, and basically said it was nice meeting me but she did feel the ending of our date was a bit awkward and would not like to pursue another date, and wished me good luck. I kind of saw it coming but at the same time I still had hope. I replied that it's a shame, but thanked her and wished her good luck back. I really really pondered asking for more precise reasons or apologizing for coming on too strong, but in the end I settled on that simple short text.
In your experience, can initiating a kiss too early result in ruining everything?
Am I just terrible at reading signs and she had already decided, or do you think she still was on the fence?
Is it ever worth it asking for more details after a rejection? I mean it's too late now, but for future reference…
Do you think it really comes down to me "messing up" the ending of the date? This thought is hard on me, she seemed to show interest and really reciprocated conversation, which has not happened to me since years ago; here I'm left feeling I completely blew it for stupid reasons.
I had planned an activity date but with everything closed down, I just asked for a simple meet up and walked around town talking, stopping at a few shops here and there, is this a bad first date?
I kind of knew this was coming, surely my first date since the end of my relationship a year ago could not be 'the One', but it still hurts pretty bad, I have a really hard time building my confidence and self worth back up. Any advice? or any other relevant feedback…
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