Whenever I see someone I'm interested in I always make sure I go and talk to them. That's as far as I've ever gotten.
The way I see this working is as follows:
somebody catches my eye
I go over and talk to them
we get along well, stuff develops in pretty much the same way as if I had just met a new platonic friend
???
We start holding hands. I've watched enough films to see that it pretty much escalates by itself from there.
The problem is that whenever I've done this, they were either cool but didn't show much of an interest in me, or their personality didn't resonate too deeply with mine which was a shame because I still thought they were gorgeous.
Now I'm not looking for somebody to spend the rest of my life with. Because that will take a lot of meeting people. But I am in the mood to experiment with intimate relationships, and now. Part of me wonders whether it's even worth it if they don't share my sense of humour. But another part of me thinks the steps above might be constraining me to only one type of relationship, those of the lifelong sort, which is why it's taking so long.
As you can see at step 4 there is clearly a gap between talking with them and holding hands that I don't know how to cross, which I'd currently do by explicitly asking can we hold hands. I wonder if the thing I'm missing is also the thing that would progress things to the physical without the person being your soulmate. When you go to parties you see drunk people breaking the touch barrier together without talking. What's the cue for that to happen? Should touch ever be the thing that advances a relationship with someone? How does that work? How do you make sure it's mutual? Or is the way to go really to wait until I meet someone I get along with so well that something clicks?
Your step 4 is to ask them on a date. Not to hang out as friends but on a real date.
You could say something like "I've really enjoyed spending time with you and am wondering if there might be more than friendship here, would you like to go on a date Friday? There's a show I think you'd like and I'd love to take you to dinner before?"
This step ensures that you're clear there is mutual interest. Then when you're at the show you know it's likely appropriate to hold hands and see if the spark continues, grows, or shrinks. If it continues you can take it as fast or slow as you and they feel comfortable with while checking in regularly by saying things like "I'm really enjoying this, would it be ok if I kissed you?"
You are the only one who knows your comfort reading social cues (and honestly, I still check in like this with my wife who I've been with for 16 years from time to time to ensure I'm not misreading cues).
Be up front and clear about what you're hoping for at each step and open to the possibility that they might be hoping for something different!
You're right. I was thinking there's a step 3b where you casually touch their shoulder or something to see if they hate it (which is probably how the drunk people in op's picture have done it), but much better to use your words and see if they're on the same page, then proceed confidently.
When you're sitting close to each other, literally say, "do you want to make out for a little while?" Only do this if you know what the answer will be. I like this because it's not some super corny line, but it's still kind of funny. Not everyone wants you to grab them and kiss them like in the movies. It's important to get consent. This silly line has worked for me every time, because you should already know the answer. They're usually just waiting for you to ask.
I'm 36. It worked with 5ish women before I met my wife (worked with her too) while dating in my 30s. The sillyness is in some ways the point. Don't take it too seriously, and only ask if you know the answer. Humans give lots of social cues when they want to be intimate: eye contact, smiling, touch, scooting closer, flushed cheeks, incidental contact of the knees or hands. Read those cues correctly and it won't really matter what words you use because you will already know they want to. And humor is attractive.
For whatever reason, probably societal conditioning, women tend to expect the man to initiate intimacy. It's scary and nerve-wracking and a lot of pressure. But just throw this line out there. The worst thing that can happen is they say no thanks and you move on.
I've found that women, even and perhaps especially adult women, enjoy playfulness, fun, and jokes. The world is serious and difficult. Dating can be a huge pain in the ass. Finding a partner that makes you laugh is often one of the top things women are looking for in a partner.
I doubt you're going to love the answer but it's basically "you just know."
It super depends on the person, the moment and the vibe. If it's been a date or two, maybe we'll be talking, turn face to face, the conversation fades, we're looking at each other and we both know we're gonna kiss, so we do. If we're all dancing, maybe you lock eyes and kind of slide into each other. Maybe you're at a party and jokes lead to childish bumping with your shoulder on the couch or whatever and you see how they respond.
If I had to boil it down for non drunk dancy events (those are just raw physical chemistry) as simple as I can it'd be something like (also, I'm just assuming genders etc, adjust as necessary):
Is she laughing at your jokes? Is she actively engaging in the conversation or just being polite while you talk at her?
Sounds dumb but is she playing with her hair? Looking into your eyes? Leaning in?
If this is all fairly new to you, then I'd play it safe and at some point in the conversation find something you both enjoy and could do together (maybe you like the same terrible dive bar, maybe there's a nice walk nearby, maybe somewhere fun for tapas) and then later on, when you think things have clicked, say something like "it's been amazing meeting you, but I really shouldn't abandon my friend Bill, even if you are way funnier and probably better looking. But maybe next week, can I buy you a drink at that dive bar/walk/tapas?"
Be prepared for rejection. It happens. It's not the end of the world, though you might feel it is at the time.