How to stop overthinking simple stuff?

[etoile]

A little backstory for context: I'm a 25 year old woman. I've been single for the past 3 years (by choice, I've been really enjoying the single life!). Before that I was in a (very shitty) relationship for 3 years. I only recently started thinking about maybe getting into a serious or semi-serious relationship again, and realized I have very little experience with this sort of thing. I've had quite a few one night stands, FWBs and short-term flings, but have done no "serious" dating.

Now, I don't really have a problem with meeting new guys. I'm fairly attractive, have a wide social circle, go to lots of social events, have no trouble talking to strangers at these events, and I can be quite good at flirting, too. The problem is that I can only do it if I'm not really interested in the guy (i.e. the most I see happening with him is a short-term fling or casual sex). Once I meet someone I see as a potential romantic partner, my brain goes crazy, one half imagining stupid "happily ever after" scenarios, the other half thinking about stuff like "is it weird to hug him when we say goodbye? what do I normally do when I say goodbye to people? what do I normally do with my hands? is it okay to add him on Facebook, or would he think that's weird and stalker-ish?" I always try hard to shut this down because on an intellectual level I realize it's bullshit, but it's usually pretty hard, and I'm probably not as good at hiding it from those guys as I think I am.

Case in point: my most recent crush. I talked to this guy twice at different social events, both times in a group of mutual friends. The second time I thought there were some signs that he might be interested, but he had to leave early that night, and by the end of it I still wasn't really sure whether or not something was there. I then added him on Facebook, he sent me a message to ask if I got home okay the other day, I said yes and that was it. I considered asking him out, but was terrified and decided to drop it, and that if I run into him again at another event I'll do it in person (I prefer in-person communication for this sort of thing, because you can pick up hints from body language, tone of voice and such).

Then nothing happened for 3 months. I had a short fling with a younger guy over the summer so I kind of forgot about the whole thing, but recently this guy popped into my head again, and I figured I should try to ask him out. However, I've now spent a week trying to decide how to do it. Take my dislike of online communication together with my tendency to overthink stuff, and you've got me spending hours trying to come up with the perfectly worded message to send to him, wondering if it's weird to message him out of the blue after 3 months of silence? Do guys even like being approached like this? Was he interested then, and even if he was, would he still be interested now? And so on, you get the idea.

I realize this must sound really stupid but I would appreciate some advice, both on this particular situation and on my overthinking in general, since it seems to be a recurrent problem.

[litterature]

Ask him out! Maybe you could have sort of a "pre-date" to reestablish contact in person, but the point is to gain momentum rather than losing it, so the more direct you are the better (I think). As for the message, I think it's best to keep it short and to avoid stuffing it with too many feelings, but don't hide anything either (this is the official DNL party line I guess?)