What's the best way to help someone find a relationship?

So, a friend of mine is nearing 30, and still single. He has a very good income, and cannot for the life of him get a girlfriend. As a result of which, he is getting a little depressed about it… which in turn is making him harder for him to find one. I think that his problem is that he is trying too hard… and he is a little picky. Since he is so successful, he wants someone who is equally professionally driven as he is… and most people that do online dating are not like that. I, being the good gay friend that I am, will be taking him to a gay bar soon so he can hit on one of the bachelorette parties that comes on through there. I guess what I am asking is, how do I tell him to just calm down and not be depressed about it, when saying calm down and don’t be depressed about it doesn’t work?