Well, I know after 20 years I definitely have bad taste in men. But right now I'm not settling for just sex because we haven't had it. I told him I wanted to know him better first. I do suck at playing hard to get and probably look too available.
I'm confused about some mixed signals from him. On our date a few days ago he did a few romantic things. We were at a bar and he serenaded me with a song. Then while we were waiting for the bus we were embracing and he was looked at me and gently brushed hair out of my eyes. We talked about our jobs / careers and the challenges we're facing. He told me not to worry because he knows I'll get through these challenges. He sounded so supportive. The next day I emailed him that I had a good time and can't wait to hear him sing more. He usually replies to my email the same day, but it's been 2 days and I haven't heard back.
Guess I am being too clingy by emailing the next day.