How to not Overthink a small situation – Kinda long!

I posted in here a few weeks ago about hitting it off with a guy who was 2 hours away. We finally had our in person date yesterday and spent 6 hours together. It was fun and comfortable. He didn’t ask that many questions about me, definitely me bouncing off him stories and asking him questions. For what it was, I didn’t mind but it did make me feel like we couldn’t really dig deep? If that makes sense. He was very charismatic, smooth and funny though. I overall enjoyed the time with him. We went for a hike, then got food. (we are both 23). We ended up kissing in his car which I didn’t mind and obviously neither did he. But here I am, 24 hours later totally overanalyzing. I do this EVERY TIME with a guy. every. time. I am becoming incredibly more self aware about my attachment style (anxious/preoccupied) and realizing why I cry and beat myself up after a date about what I did say or vs. What I could’ve said type of thing. We ended up making out in his car for longer than I expected, and he kept jokingly telling me to leave so it didn’t escalate lol. So we said goodnight like 7 times, but been overthinking how I left his car. I kind of left abruptly even though we tried to say goodnight like multiple times, I worry he took it as the wrong impression. He told me to text him when I got home and I did, and we were both exhausted but I said how I had fun tho even though we were both sleepy. He told me he had fun too and that he’s down for a second date. So far nothing over text since last night.

I don’t have expectations as we have a distance thing and he told me he did want to have sex at some point, but I said I rather get a hotel to have actual space instead of a car to be more intimate lol. Also even though we had 3-4 phone conversations he JUST told me after I asked him – he is planning to go back to school in the fall, literally by the end of august. He was super vague but he just told me this now???? I had a gut feeling this would be a fling, even though he told me he was looking for a connection and isn’t into hookups, so idk what to think. After a year of rotating shifts (and this was my first date and kiss in over a year) working from home in my toxic house with my alcoholic father with no car, my #1 priority is to find a job in NYC and make the OFFICIAL move. I wanna re-enter society and have my own independence again. So him starting school, and me finding my next job and making the move (cause right now I feel like I am in purgatory) feels like this is screaming super casual. I felt ok with this before going in as I haven’t had fun in a LONG TIME, and now look at me, typing this out feeling silly and partially ashamed?

Each time I think I am ok going into this, I start to nitpick everything I did or done. No matter what the dude. Looking back I only really liked one guy I have been intimate with, and he ended up breaking my heart during that phase after 2 months where the guy decides if this is worth it or not. The other men I didn’t really “like” (some of them I enjoyed their presence sure but felt no romantic connection) yet knowing this I STILL put it all on a pedestal, got extremely anxious when they did not text me, and made the whole situation have arms and legs. so I am really trying to navigate if its a self esteem thing? Me feeling shameful after having sex? Still processing it all.
It’s sad bc I wish I had 4 guys like this in rotation right now just getting to know them & having fun ya know? I have a feeling in a city I will finally be able to start these new experiences and navigate what I like and don’t like and notice more how I react. I feel like I am being too picky but I also know what I am looking for, but no matter what I feel like – I get upset.

Back to this guy, the ball is 100000% in his court to plan the second one. It might very well be a bit more spontaneous that I would hope, but I also think he is definitely speaking to other girls. He told me he needs to prep for school and other housework before he leaves, so another thing to add to the list of “casual”. He also said a few things during the date that he claims that I have said yet I had to correct him that I never said such a thing, and at one point I almost said “wrong girl maybe?” but I did not lol. We were both also incredibly tired so I am giving him some leeway but who knows. The few times I did get open and vulnerable I felt like I was sorta being judged. It was odd. Hence why I think I would *maybe* just like to have sex with him. I feel comfortable and safe with him, BUT it also irks me because if we had more time, I do think this could’ve worked. I feel insanely rushed. My gut intuition about this stuff is usually very correct, hence why I am even typing this out. As I am confused on a lot of things stepping back into this all.

Reality is: I want to stop feeling upset after a date with a man I am (even if its semi) interested in, and to stop beating myself up for what I didn’t or did do. Been doing this since I was 18. And I want to kick it aside and own my self worth.