I've decided that's my main sticking point. Approach anxiety - pretty minimal. My ability to calibrate? Probably extremely high.

Escalation anxiety / kino anxiety? Pretty significant.

I think it's from pretty basic roots - I grew up in an enormously WASP (white anglo saxon protestant) family. No hugging, no kissing, nothing - we express affection to each other via words, that's the way it's always been. Great, but that means that despite my excellent abilities to build comfort and rapport, my great sense of humor, my ability to banter, use eye contact, etc. - I feel completely out of my league when I read stuff like this:

http://whetyourwoman.com/pickup-women/kino/

In college I stumbled into sleeping with about a half-dozen different women, and then met my ex-wife (whom I am thankfully divorcing). In all cases I was the one who was pursued. I barely did the pursuing. I really, really want to stop this dynamic now before I'm an old fogey (at least, any more so than I am now as a 40 year old).

I have a few 1:1 dates set up over the next week or so. Two are from OKCupid, they're highly compatible matches, attractive, my types. I also have an almost-in-the-bag FWB that I'll be meeting up with in a week or so. I understand that kino is almost a prerequisite for showing intent in most cases with just about any woman. So here's what I want to know:

1) Is any kino escalation better than no kino escalation? I know this is a pretty obvious question but I'd like to hear the answer anyways.

2) Tips to make it more natural for a WASP-spawn like myself?

3) Tips that are relevant for 1:1 "date" kinds of situations rather than bars, clubs, looking-for-one-night-stand kinds of situations? An f-close on the first date would be great from any of these women, but really all I care about is moving the ball forward with one or two of these ladies.

Thanks for your advice. Great subreddit, glad I've found it.