It's a little strange...but it's not that bad. I would just make sure he gets permission from the drunk chick before banging her. Also make sure she's not that drunk that she could pass out and cry rape. Also do her at her place and leave before said drunk chick wakes up.
Also I would not do this. I would simply pace myself and only drink a small amount. Going in stone cold sober takes some stones... I don't think I'd ever be able to pluck up the courage to go and try to chat them up. You need a few drinks to handle the rejections
I have a friend when he was single used to go around every chick in the club and try it on with them. He would go through about 20 no's until finally one said yes. Personally I couldn't handle all that rejection...but it's just a numbers game and it worked for him.