About a month ago I [24F] almost hooked up with this guy [29M]. We were both drunk to the point that neither of us remembers who initiated it.

Anyways, he didn’t contact me afterwards, so I let it slide.

We aren’t friends (we only talked a little that evening and maybe exchanged couple of sentences before) but we have some good friends in common. They all say that he’s a great person but that he’s shy and quiet. Like extremely shy.

Can confirm, as I’ve seen this guy after the hook up twice and it was always the same story: he saw me, started acting extremely awkward (in the sense of body language) and very obviously kept staring everywhere else to avoid an eye contact with me. He said a quiet “bye” when he was leaving the restaurant I met him at, but he didn’t look at me.

This could also mean that he doesn’t like me and has regrets or whatever but that turned out not to be the case: we hooked up after we got drunk at the same place again this week.

At first he talked to me very awkwardly, just couple of notes about something here and there and talked to me progressively more through out the evening. He knew when I had my birthday and how old I was, about my family, you know, stuff like that. He had to ask someone or check my SM. He also told me (with a little help from a common friend, who was like his wingman first half of the evening) he likes me and that I’m very beautiful. I asked him why he didn’t contact me, he didn’t exactly answer, just said “why didn’t you”. I said that it would be stupid, he said definitely not and “text me”.

We attempted to sleep together later but he couldn’t fully get it up, I guess due to the nervousness and alcohol? I assured him that it’s not a bad thing. He was obviously a bit annoyed and disappointed about himself, but there was no terrible melodramatic scenery. He told me that he likes me a lot again after. The foreplay and all that before was amazing, though.

He texted me the next morning and we were texting for a bit, though nothing too great. He then stopped. I asked him why he stopped talking and he said that he’s not talkative but that he’s not mad at all or anything, maybe at himself. I kept texting him (and tried not to be annoying, really) and he was answering (sometimes even in long sentences that often didn’t even make sense tbh, like he seemed nervous but not bothered), but never asked me anything.

I grew tired of that and asked him if he wants to grab a coffee on a day when he’s definitely not supposed to work. He said he’s “playing tennis” (obviously, you don’t play tennis the whole day, which I mentioned to him with an easy going tone to it all). He explained it’s indeed a whole day thing (which okay, it made sense it would be the whole day in that scenario, but still), however he didn’t give any alternative. I told him we can go the day after and assured him that it won’t ruin my ego or that I won’t get mad, if he just says “no, I’m not interested”.

He said “We’ll see about [that day] :D” and went to sleep. Didn’t hear from him ever since (it was yesterday).

Do you think this guy is into me but like… very snake bitten? Or does he just not give a fuck?

What should I do? I don’t want to be an annoying chaser, you know. But people who know him told me he’s definitely into me, just shy.

Should I text him the day before the day we should see about (couple days away) or should I just let it be? Assuming he won’t text me himself (likely). If he’d come up with another excuse and no alternative, I’ll definitely let him be then.

Edit: A bit of context. Guy is in late 20’s and had one girlfriend for like two years. She’s the only one who he had sex with. He really is super shy.