That's your opinion about yourself that he's more attractive than you, which also shows that you don't place too much value on yourself.
I don't know the guy, but if you l go on a date with someone while having a pretty low self esteem, the chances are that he's going to see through it all & press your buttons in the long run, since he knows your weakness.
If I were you, I would work on the self esteem first and then date someone when you are ready and know what you want. If physical features were all that is required for the relationship that none of the celebrities / good looking people would break up with their partners.
Yes and no. I think it's best to date someone of equal attractiveness levels, since neither of you will feel like they are settling. I'm not saying equal looks, I'm saying of equal attractiveness in general.