I have no problem with approaching girls, getting their numbers, talking to them, asking them out, holding eye-contact etc. However, I severely struggle with physical escalation and setting a sexual vibe. Just had a date and couldn't move past incidental class touching. I didn't panic at all, I remained calm and collected, I knew what to do (I probably know the DiCarlo Ladder by heart now), I just wasn't sure when to do it.

I do not have a problem with touch per se (she hugged me in the end and I was completely fine with reciprocating + I'm very physical with my bros), however it always has to be the girl initiating it because I feel unsure about when what is appropriate and when the moment is right (don't wanna ruin my reputation / get a false accusation). I think my aversion to taking the lead and escalating has to do with my childhood (raised by a single mother who was very harsh) and me not having friends in my first few years of school.

Do you guys have some tips on how to overcome this problem? It's really frustrating because the more I look back the more chances I see where I could have succeeded had I just escalated a bit.