A Gentleman Doesn't Kiss And Tell 

A play on the idiom "kiss and tell": "Kiss and Tell" implies a betrayal of confidence, typically (but not necessarily) when referring to an encounter of a sexual nature. While the phrase "A gentleman doesn't kiss and tell" was originally intended to end a conversation by making it clear that details will not be shared, it can also be used to infer that a sexual encounter actually occurred.

1) He honestly 'kissed' the girl, then later implied that he did by saying "a gentleman doesn't kiss and tell"... making him a sleezebag and not a gentleman.

2) He didn't 'kiss' the girl, then later implied the he did... making him both dishonest and insecure.

3) He did/didn't 'kiss' the girl but does not want to appear to be a sleezebag and wants to respect her privacy.

1)
Tom: So, did you fuck her last night?

Max: A gentleman doesn't kiss and tell *wink*

2)
Tom: So, did you fuck her last night?

Virgin Max: A gentleman doesn't kiss and tell...

3)

Tom: So, did you fuck her last night?

Max: Don't ask me about it Tom. A gentleman doesn't kiss and tell.

A Gentleman Doesn't Kiss And Tell by Marauder91 April 29, 2016

A Gentleman Doesn't Kiss And Tell 

An expression used by a self-conscious dude who wants his friends to think he got laid. Generally used right after a date or when asked if said guy has ever rolled in the hay.

Jimmy: "Hey man did you f*ck her last night?"
Carl: "A gentleman doesn't kiss and tell"
Jimmy: "P*ssy"

A Gentleman Doesn't Kiss And Tell by DieZelBag August 13, 2015