I know I'm damn smooth! That's why the call me J-Smooth my man. Okay, enough of the DHV bullshit and time to get down to business. So you didn't hang out because of your damn ex. Okay so in this scenario, here is what I would say.
"I was thinking about High School the other day for some reason, and I remember you were such a geek back then, good thing you grew up!

Anyways, how have you been doing? Is your mom still dressing you, lol

!"
Just have fun with it, use smilies and stuff to show you are being playful. Keep some negs in there. If she doesn't mention a boyfriend don't worry about it, trust me on this.
Have fun,
