This has been my problem my whole dating life. I get a good conversation going, build up attraction, flirt to a certain level, but when it comes to the 'physical' flirting, I freeze, or keep it very innocent like put my arm around her shoulder or maybe slightly around her waist.

All my female friends tell me I'm very good looking but in that cute or handsome way, I look LOOOT younger than I actually am, I'm 28 and can pass for 16 if I wanted to. This used to bother me, but I realized that it works to my advantage because girls are not intimidated when I approach them, and I usually get a positive reaction when I talk to them.

I have a nice exciting life, and I'm usually around lots of girls, and I do alright with them, but I only make a move if I'm positive she's 100% into me so I wouldn't get turned away. I've been noticing that more girls like me than I actually thought, and that I missed out on a lot of chances because I escalate just enough then I stop and tense up.

My question is, how do I physically escalate without coming off as creepy or 'friendly'?