A recent encounter I had at a neighborhood bar:
I walk in with a few friends, and sit down at a table. A cute blonde waitress soon comes to take our order. Hoping to get a smile out of her, I look up and tell her, "We'll start with a round of Strong Island Iced Teas."
Expressionless, she nods and says, "OK."
Not a great start, but like a jackass, I continue. "That's...like a Long Island, but stro-"
"Yeah, I got it," she interjects, and walks away.
Sometimes, trying to be a smartass leaves you feeling like a real dumbass.