On our first date I'll most likely poke fun at you in some way with a wry smile and a wink. I'm not good at winking though, so you'll probably make fun of me back. Then we'll laugh and sip our drinks. It will be great and not at all awkward or contrived.
Also, I have a dry sense of humor.
Also also, looking at Leonard Maltin makes me giggle. It's always better when people are funny by accident. He might be the best at it.