Classy Gentleman 

Generally used to describe some after getting completly obliterated (drunk), and doing some very questionable moves after.

Brian, and Bob at the bar
Bob: Wow i think that chick is totally got me in her sights.
Brian: Most definetly... but i think she is a little out of your weight class, try and keep it under 200 pounds.

After the bar is closed bob is outside making out with said women, while everyone in the bar is outside trying to find a way home.

Brian: bob you totally were showing everyone in the bar what a classy gentleman you really are.

Classy Gentleman by uofa October 11, 2006

Classy Gentleman's Handkerchief

Commonly called just classy gentleman. For when a guy wants to jack off covertly and needs a mop up rag but has nothing to use, So then the guy uses his boxers to clean up and then goes commando with the dirty boxers hanging out of a pants pocket. Usually done if a girl gives the guy major blue balls and he doesn't want to make a mess of her bathroom getting off. Thus the name from being classy enough to not make a cummy mess at a girls house.

Carl- Damn dude, Rebecca was being a prude bitch last night and wouldn't give me even a handjob. So I was stuck with blue balls and a major chubbs, so I went into her little sisters room to wham the ham, but I forgot mop up material so I had to beat it into my boxers. Then I just did the classy gentleman's handkerchief until I was able to get out of there.

Derek- What a bitch. That's a classy thing to do dude,

Classy Gentleman's Handkerchief by The Bro13 August 14, 2009