I have been to comic con going on my 4th year running this weekend and I haven't payed a single dollar for any of it. I have a female friend that has always given me a free pass and never asked for anything in return. This year she tells me that she has extra passes to go and that she is deciding on who to give them to.

Two weeks later, I am climbing with a buddy that has known this girl for as long as I have and he told me this week that he has always wanted to go to comic-con. Now this guy is seriously submissive to the point where he will absolutely refuse to tell you whats wrong if something is bothering him, completely avoids altercation at any cost, and assertion from him looks like "I think we could do X since Y is something that might not work out?".

Well this girl apparently knows that he has wanted to go to comic-con and guess what, he didn't even know about these passes that she has. She actually owes him $100 right now to boot. So I tell him "You better fucking get a ticket."

This is a close representation to the text he was about to send her. "Sooo... I was thinking.... You know that $100 that you owe me? I was thinking maybe you could just repay me with a trip to a certain convention?" And then he shows me the text before he sends it, why I have no idea.

Now I know exactly how well this message is going to be received. Ultimately I laugh and say you are not sending that text. She owes you 100 dollars. You better re-write that, and don't ask her to go, tell her you're going.

He re-writes the text with a little help from me to say "Hey X, I heard you have extra comic-con tickets this year so I'm coming with you and just_a_handsome_guy."

She responds almost immediately with a simple "Okay :)"

Being assertive with women is something I feel like guys have a very hard time with, and it's not something to shy away from. He didn't give her the opening for an excuse and now he gets to come to comic con whereas he wouldn't have even known about the tickets.