a way to describe a person claiming they are gonna do something however, the complete opposite happens instead.
Kenny: Hey watch this I’m gonna spit my game
Friend: Okay.
Kenny: Hey wsp cutie how old are you?
girl: “no”
Friend: bro that’s such a kenny moment.
Friend: Okay.
Kenny: Hey wsp cutie how old are you?
girl: “no”
Friend: bro that’s such a kenny moment.
by pizzafan April 16, 2021
A point in time when a situation is "can't win," as evidenced by all facts and reason...and you need to "know when to fold 'em."
I was going to show the pictures of my soon-to-be-ex-wife with that chain gang, but then I had a "Kenny Rogers Moment" when she brought out the pictures she had of me with the (male) principal of our daughter's school.
by ManiacMike August 13, 2009