<human>: Summarize the given text in a few sentences.

Back story is as follows:

I am a married man, but my best friend is the most single man I know. I want to help him find a woman or at least boost his self esteem by helping him get a number at the least.

He has only had one meaningful relationship in his life, and he has trouble meeting women. He isn't the most social type and he's kind of nerdy looking haha (tall, lanky, glasses, etc). 

I have been out of the dating game for the last 5-6 years and I want to help him, but I've never been a good wingman. I'm looking for suggestions to help him get a conversation going with ladies at the bar or other social events, more than the "Have you met Nick?" game.
<bot>: What are your best wingman tips for guys who are just trying to help a friend without having to sleep with the chicks friend?