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.
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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"
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