How should I be acting around my crush?

My friend (who I also have a crush on) and I go out to bars and concerts maybe once a week. We are (unfortunately) strictly platonic. When we go out, I frequently get hit on, but my friend is not so successful with the ladies. The same thing happened last night, with two people hitting on me and my friend getting shot down (the girl he was hitting on ended up hitting on me!). Anyway, he's really down on himself today and keeps talking about how he is so unsuccessful with the ladies. I feel bad and definitely don't TRY to get hit on, but I'm a friendly person and I'll talk to anyone. The problem is I really like my guy friend and would like to be more than friends. Do you think my "success" with the opposite when we go out is actually hurting my chances of his seeing me as more than a friend? How should I be acting in those situations? Should I be trying to boost his ego with women?