Vince Vaughn's Trent in Swingers...

He's so money.

He was a complete mess, and just hid it behind a false sense of confidence which is why he chose to hang around people that looked up to him so much making him feel superior.

The final scene is the most real glimpse of his psyche we see in the whole film.

He would be fun in small doses but would get his arse kicked if anyone was around him for more than a night or two every few weeks. We've all had a friend like that at some point

I watched it again last night. Read the IMDb info. Theres some pretty interesting facts about the making of Swingers.