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!