Any psychological advice would be greatly appreciated?

I am shorter for a guy, I think 5'5, my girlfriend is about 5'8, I always said I would never date a girl more than an inch taller than me, but there is an easy way to make a guy forget about height. The best is when you sit on a couch to watch a movie, lay down in a ball and put your head on his chest, as long as you can do what a smaller girl can do then its not really a big deal. My girlfriend always puts her head on my chest and curls up in a ball next to me and it took me about 3 months to realize how much taller she was. I am not going to say the height difference for you is the same but I think as long as you let him be the "man" in the relationship, he really won't pay much attention to it, and also if he is continuing going on dates with you then I doubt he cares to much about your height or he would not keep going. Do not worry about sqeezing his hand either, you have to do that because if you really do end up becoming serious then it will be more awkward if you do it then and he isn't used to it then, you should not have to hide things you like to do, if he really likes you he will learn to accept it.