Wear one of those nice sweaters that exposes the sides of your upper arms/shoulders so he feels invited to put his arms around you; wear a loose fitting bracelet or bangles on whichever hand you want him to hold. By wearing a bracelet it will give him an excuse to pay attention to your hands, and is also very sensual. Wear your favorite pair of casual jeans & flip flops..make sure your toes are painted (maybe a dark purple) & maybe even a cute toe ring...
There you have it, a casual/sensual/comfortable bohemian look, that's not over the top and makes you look like the sweet heart/girl friend type.
I don't think what you wear will be nearly as important as how you act. Just relax and be friendly. You went to the prom with him and survived with a friendship still in tact. If you have the opportunity to hold hands, hold his hand with both of yours and gently raise his hand to your mouth and give it little kisses. He'll love it, it's innocent enough and should give him the message that it's okay to kiss you too. Once you've passed that awkward barrier things should rock along nicely. Good luck, and by all means have a lot of fun. If you really enjoy this "date" there is a good chance there will be many more.
Wear your thong.
Well, as a man with many years of experience, I would say to wear what you want according to what you want to have happen!
Let me explain. I like putting my arm around my movie date so if her skin is exposed on her shoulders and neck, then I'll rub those areas gently during the movie.
I like to kiss during a movie so if her face is not blocked by her hair from the side that I'll be sitting, then I'll lean over often to kiss her cheeks. If she turns to kiss me too, great!
I like to hold hands during a movie, so if her hands and arms are exposed, then I will hold her hand and gently rub her arm with my free hand.
I like to get frisky during the dark movie passages so if her breasts can be easily accessed then I'll get her hot by rubbing all the right places! If her mini skirt is short, and she has no panties on, then I will reach down there and rub that very special place.
At all times I am totally aware of her reactions to everything I do. If I feel her resist even just a little bit, I will pull back and stop what I'm doing as I apologize for losing control. Most first dates don't let me go far, but girlfriends usually let me do it all. If she doesn't want to be touched somewhere then she'll cover it. Simple as that! :)
if he likes you for you then be yourself.
low cut top to get him going and maybe knee legth skirt or dark holy jeans and colored pumps to match with ur sexy jewilery no arings and most exspense purse so u look fab show off ur **** thats what i doo have fun girl or u can dress how u usally dress up to u good luck
dating always make you feel young and exciting, go accessible.