@Turned Out Nice Again, you come across as a top bloke, but are over-thinking it I think, which is a confidence thing. I'm only a decade younger than you. I'm no expert, but a few tips from someone who divorced 7 years ago. This is what works for me:
Date 1: Drinks only, 2 hours max. If you see a lot of IOIs (indicators of interest) such as her touching her hair, touching you on arm, fluttering eyelashes, by all means escalate and try to get her into bed, but if you want a relationship rather than just a shag, hold back.
Date 2: Make it interesting, multiple venues, not just dinner. So could be a walk, followed by art gallery/karaoke/whatever, followed by meal, followed by bar. Venues where you can be side by side, not opposite each other, so you can touch (very important!). Be diplomatically tactile touch her on arm, lower back etc ("kino") and if she reciprocates after a while go in for the snog (push and pull - snog but then hold back). You could try to shag her at this point but I usually wait for date 3 as it's the shag date and girls know it.
Date 3: Suggest she comes to yours for dinner, or go away for the weekend. If she says no then drop her, there will be no action at any time. If she says yes, then sex is guaranteed.
- Say as little as possible. Women build their own narrative and will create a picture of you that they find attractive. A quiet man is a confident, mysterious, sexy man. Just confirm it. Let her speak about herself.
- "Shit tests" - read up on this as girls will test if you are worthy. The best response is "agree and amplify". So if she says "I don't like your car" then reply "I don't like it either but there's room in the back for an orgy".
- YOU ARE THE FUCKING PRIZE! Seriously, there are very few good men about at this age (40-60) who are fun and fit and the burds know it, but they try not to show it.
- Keep fit, do weights (it's a cliché but it's bloody true)
- Be a good shag, very few blokes shag well. If you do that, once you've shagged on two occasions, they're yours.
- Confidence: The thing girls are most attracted to. Appear confident even if you don't feel it. Tell her where you're going/meeting, don't ask. Girls hate a bloke who can't make decisions or seeks permission.
-Go 50-50 on the bill or take turns. The ones who never pay either won't put out or are crap shags as they're entitled.
- Don't stick to one or go exclusive. Play the field. There are lots of good burds out there. Once you've had one or two you'll have that aura that women pick up on that you're attractive.
- Do a mixture of dating (local pickups, online, etc), it's a numbers game, improve your chances.
- Personally, I don't see the point in whores when I can get good women who are DTF enthusiastically. I want burds who want to fuck me because I turn them on not because I paid. Last week, on the same night, I got texts from 2 good looking younger women (both in very good jobs, not skanks) who both basically said "I want you to fuck me hard, right now". BTW, I'm no movie star, I'm early 50s and a short arse, and I used to be as beta as they come.
- If your gut says "she wants it", trust your gut, it's true!