Who looks good in hats?

This date was set up as though we were going to be hanging out in a big group, but ended up just being the two of us. He was cute and saw this as a wonderful opportunity. We went to the new James Bond movie at the time and later went to play pool. I was never good at playing pool and he wanted to play that the loser bought dessert. I didn’t have any money in my purse and so I knew that I needed to win. I got a few good shots and was doing better than expected; he was doing just as well though. He had gotten down to one ball and the eight ball left; I had a few more than that on the table. This was a time for desperate measures. I had heard once that the most tender spot on the body was right behind the ear; I figured I would test this out. As he was getting his shot all set up I slowly walked behind him and blew ever so gently on the back of his neck and up to his ear. I have never seen anyone drop to their knees that fast; I guess it really is the most tender spot on the body. I ended up winning because he knocked in the eight ball, and I cleaned up.

I must have left a lasting impression, because he invited me to come and play football with him and his friends (or it was pay back?). Now note that it was WINTER time and we were playing football; I showed up all buddle up, and he looked surprised. After playing for awhile, and no one could feel their fingers and toes, we finally called it a day. On the way out he walked me to my car and mentioned how I looked different then the night before. I asked “how so?”
“Well I remember you looking nicer.”
“Because I did, today I came prepared to get dirty.”
Touching my beanie on my head he looked at me and said, “In all honesty, you look like a hobo today.” I’m pretty sure one of my ‘are you kidding me glances’ came out at that point, because he continued,
“I just was telling all my buddies how pretty you were and I was excited to show you off and then you came like this.”
To which I just said, “I’m sorry that I embarrassed you, but what were you hoping I would come dressed like when we’re playing football in the snow?”
He tried really hard after that to get his foot out of his mouth and I wasn’t helping him at all. Finally he just ripped the hat off my head and said,
“I’m sorry Linz but you just do not look good in hats, they make you look like a homeless person.”