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Gentleman's Choice 

A Gentleman's Choice is when you pick up both a mother and a daughter, at different times, and must then make a choice between the two at a later date.
Raul met this chick at the tailgate party and hooked up with her that night. The next weekend, he picked up a cougar and woke up in the same house as the weekend before. Over the course of the next week, he had to make a Gentleman's Choice about who he was going to see next weekend.
Gentleman's Choice by Texifornia January 28, 2012
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Gentleman's Club 

Defined as having sex with three different women in a 24 hour period. Girlfriend's and foursomes don't count.
Tony brought a girl home from the bar on Friday night and banged her. Then had a tinder date with another girl last night and railed her in the bathroom at the restuarant, then later that night he brought home yet another girl from the club and laid pipe. He's now an official member of the gentleman's club.
Gentleman's Club by Kike Hunter April 24, 2017

Gentleman and a scholar 

Ray looks at sheep all day long, but still has time to help me with fractions, which is why All-Day-Ray is a gentleman and a scholar. In fact, he is 60% gentleman and 40% scholar.

Gentleman's Handshake

When two gentlemen jerk off another gentleman using a handshake. All gentlemen must be wearing suits.
Hey, I'll give you two guys $30 to give me a Gentleman's Handshake.

Gentleman Ghost 

A dude who does it with dead dudes, amongst other activities on the circuit
He's called the gentleman ghost because he likes to get it on with dead dudes
Gentleman Ghost by MarcLopez September 26, 2005

gentleman's handshake

When a male performs a tugjob on another male with the top of his hand.
The other night Tommy and Jeff were so drunk they stood across from each other and gave each other gentleman's handshakes.

gentleman scholar

Someone who is in school for a perpetually long time, for a scholarly degree that has no practical use in the real world. Usually describes someone who comes from a wealthy or aristocratic family since pursuing such a degree costs a lot of money and won't help the individual obtain a job. In polite societies, may be used derisely to describe someone as a "professional student".
Catherine: Ah Mr. Darcy, the last time I saw you ten years ago, you were pursuing a Philosophy Degree at Oxford. What have you been up to now?

Mr Darcy: I am attending Harvard and working on my Ph.D. in Western Mediveal Literature.

Catherine: Oh that's nice. (Mockingly) You're quite the gentleman scholar.