I very rarely wear wigs. I wear them once a week maybe once every few weeks. I wear hats or scarves almost daily. Usually I wear a wig for special occasions or for meetings. I went on a great date with this guy last night and I had a meeting earlier that day so I wore a wig to meet him. We both had a great time and he was very adamant about us setting up a second date before thanksgiving when we both go out of town (so I know he likes me thus far). We met online and in my photos I have two bald pictures and one fairly obvious long red hair wig photo. I realized by meeting him with the wig he could either think 

1. My hair grew out from those bald photos

2. I am bald but I wear wigs regularly.

I don't want to give him the illusion I like to wear wigs (at all) by wearing one on the second date just to fool him into being attracted to me but I also really like him and don't want to be foolish and do something drastic that may detract him from me prematurely. Should I opt for the hat or wig on the second date? I want to wear a hat of course, but when is a good time to present to him my daily head wear? 2nd or 3rd date or do you think it does not matter if he already likes me?

p.s. this is my first time actually liking someone after being bald these past 8 months. :/