[Hotwheels]

Not much you can do differently. He has to want to fix himself.

I don't help those that make no attempt to help themselves, and your friend did nothing in the described scenario to help himself. It is a waste of time and ends up causing rifts.

If your friend doesn't want to get laid he won't. If he wants to he will take steps to move in that direction.

Your only option that I see in that situation was to shame him.

Which often leads to the aforementioned rifts...