So what do I do? Did I walk away too early? What do I text him? Try to get to know him over text? How would I even start that? Or just ask to meet up at a coffee shop or something? How do I not sound desperate? Do I need to wait 3 days or whatever social rule bullshit exists? Did he just exchange numbers to humor me to get me to go away?

Over-thinking, the assassin of progress.

Message him “hey, nice top, hope you got home OK”. Then forget about it.

Do the same thing with someone else the next time you are out, and again. With a number of hooks in the water you won’t spend the time worrying that the first guy hasn’t got back to you (because it’s rarely about you - life happens).

I wouldn’t worry too much about social rules about waiting 3 days.

You want to temper your personality if you have a tendency to be excessive but if you do things that are really counter to your nature then you’re going to give false impressions and sooner or later you’ll be faced with a choice between continuing to keep up the act, which is not good for you or the potential relationship/friendship, or to drop the act, which generally leads to rejection because you will appear to have changed in the eyes of the other person.

Think about this like clothes. You don’t want to be wearing something that absolutely isn’t your style. You want to wear something flattering that represents the best parts of yourself while minimising the flaws. You don’t want to wear your awkward, unflattering house clothes.

In a similar way, you want to present a good version of yourself that minimises the flaws but which is still authentic to who you are when interacting with them.

Next, strike up a conversation with them via message. Tell them that it was nice to meet them and maybe say something like “I would’ve spent more time chatting to you but I’m kinda shy”, except in your own words. Ask them something general in the same message - did they have a good night, were they out for an occasion or were they just having a night out, do they go there often, that sort of thing. But only ask them one question.

Let them respond before your next reply. Hopefully they’ll respond with a question for you. Acknowledge what they said, e.g. “Yeah there was a good vibe there the other night. I had fun too.” if they said they had a good time, then answer their question and reply with a follow up question that is still pretty general and not too personal.

Keep the back and forth going like that but get more personal on questions gradually or as per their signalling. E.g. if they tell you they were out with friends then it signals that you’re allowed to ask them if they are friends from college or something to that effect. If they tell you they were out for a friend’s birthday then it signals that you’re (most likely) welcome to ask how old their friend was turning. That sort of thing.

If they show an active interest in responding to your questions and (especially) if they reply with questions for you that’s a good sign and, eventually, you’re either going to have two options:

1. Tell them that you have a tendency to miss cues and that you appreciate directness

2. Try to wait for a cue when they bring up the next time they’re going out or that they don’t have any plans for the weekend and interpret that correctly and do the social manoeuvring to ascertain whether they are inviting you to meet up or they are signalling to you that they want you to offer a suggestion to catch up for coffee or something similar

Option one is easier on you but it’s asking them to take a fair degree of risk of rejection which often doesn’t go over so well with shy people and those lacking confidence.

Option two is harder and it often takes a degree of familiarity with the steps in the social dance of neurotypicals, which always varies depending on the other person and their cultural context so there’s really no hard and fast rules. Sucks, but it is what it is.

If you’re leaning towards option one then you can soften the blow by saying that you’re pretty direct and honest but that doesn’t mean that they have to put themselves on the line because they are welcome to ask direct questions to feel out how where you’re at and it’ll take the guesswork out of the situation because you don’t really play games. I wouldn’t word it in those terms though. I’d say something like “I’m a pretty straightforward person and tbh I don’t really play games because I’m not good at them so if I ever leave you wondering then feel free to ask me what I’m thinking and I’ll give you an honest answer.” But put this sort of message in your own words, if you feel comfortable with using it. Or adapt it to your preference.

Eventually the next step will be to nail down a time and place to meet up again that you both agree to.

I hope this is helpful to you.