This is a long one, TL;DR at the end.
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I'm a guy, been out of college a few years now (late 20s), and... I fumble the flirting / hookup bag seemingly at every turn, but I want to get better.
---BACKSTORY---
For just a bit of backstory, in college I had a long-term relationship that lasted nearly 3 and a half years. That happened quite naturally, and she made... a lot of the bolder, more forward moves. So naturally, I never really flirted during a lot of early college parties that I went to.
That fizzled out, and I went relationship-less and sex-less for over a year. Had one hookup after that time with, again, a quite forward woman who was a waitress at a restaurant I used to frequent every day.
Then I entered a long-distance relationship after meeting up with an online friend in person, and I was a bit more forward after a friend of mine pushed me to say something a little more daring. Then in person I went in for a kiss after a long, pleasant conversation (still not much explicit flirting) which was reciprocated, and that kinda sealed the deal.
---CURRENT DAY---
Fast forward to today, I've been out of that relationship for nearly 2 years, and since the end of it... I haven't had much success (a few online situationships with some explicit exchanges, which are far easier for me it seems), and I find it comes down to... a set of skills I haven't learned.
In talking to some of my friends who are girls, I hear some crazy ass stories. Or at least crazy in my eyes, but I think that is part of the problem. Hookups at student conferences, hookups at weddings, at places where you meet that same day, and I'm just like... where has this experience been in my life?
--THE PROBLEM---
I have a hard time in general flirting and expressing interest. Specifically I think introducing myself for one, and then if I get past that, moving from polite conversation to flirting / moving toward a physical relationship.
And I think this problem becomes magnified in situations like the stories I mentioned because you have far less time to get to know each other. I have a hard time judging which situations are appropriate to flirt in, or try to hookup in, or even how to go about doing either of those. I feel like I would like the ability to flirt well, or have a short-term relationship, or a hookup like that
---THE IMPORTANT QUESTION---
How do people do this? How do people go from meeting someone at a wedding, conference, or bar to hooking up with them? Like, is there any advice other than trial-and-error for navigating this kind of road map:
Strangers → conversation
Conversation → flirtation
Flirtation → romantic interest
Attraction → physical intimacy
Intimacy (touching, kissing) → possible hookup
---OTHER QUESTIONS, PICK ONE YOU LIKE---
How do you approach? How do you eventually make it flirtatious and how long do you / what do you wait for? When do you express interest? When do you make physical moves / which ones are acceptable? How do you naturally transition from a group conversation to spending time one-on-one with someone you're interested in? How do you approach groups / individuals differently? How do you bring up the idea of kissing? How do you bring up the idea of hooking up? How do you make it clear you want to hook up without wanting a relationship? How do you actually move toward said hookup?
---THE FUTURE---
I'm moving to a new city soon, so I'm planning on using it as a testing ground for any advice. The total amount of women I've approached in my life can be counted on one hand, but I want to change that.
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TL;DR How do you respectfully rizz as a guy if you are looking to hook up?