This was a good while ago, but friends still won't let me live it down.

I went on a date with a girl and it was going nice and smoothly. Near the end of the night I thought it was time to lay it on thick and broke out my favorite and greatest pick-up line. I leaned in nice and close and said,

"So, we should reduce our kerning, and possibly turn it into leading."
When she didn't get it, I was had the next one ready, "We should head out and possibly make a ligiture."

Safe to say, the rest of the night was awkward