I went out with this gem: he asked me if I liked guac. I said I liked guacamole a lot! He said watch this, he knows this waitress who thinks he's cute and always gives him extra guac when he orders it.
The first thing to enter my mind when I heard him say it was is she going to think he's cute when he's out with another woman.
We were served, and he had what I thought was the correct amount of guacamole for fajitas, and he leaned over to her and said "Hey, Darlin' you feel like getting me some extra guac?"
She said "Sure! But it's extra."
I couldn't tell if he was angry or frustrated, but I piped up and said "Ooo, I was so hoping for some extra."
He told her "Well, let's bring it on!"
And she brought an extra dollop that probably cost him a couple of bucks. The kicker was that I didn't even touch it!
And he noticed!
I get passive aggressive like that sometimes. Don't know if the lesson is learned, but it never hurts to try.