Funny enough, it was actually a rather boring experience.
The girl was painfully shy and almost impossible to get conversation out of. I was practically talking to myself and just throwing out some ideas and skydiving randomly came up. Somehow that clicked and so I made a call and off we went.
I'd never jumped before, though I had tried several times but the skies clouded over each time I drove out (about an hour and half out the city). The first few times I was really psyched to go, but by this time (my fourth attempt) I think my excitement had worn low. The girl was just... really quiet. I thought maybe the drive out there would be a bit more exciting and give us something more to talk about, but nope.
So we get there, the skies are beautiful, we go through the prejump lesson etc, and up we go. It's a few minutes to fly up and it's againly weirdly silent. Even the jump instructors are looking awkward. We're doing tandem jumps, and I'm strapped to a guy dressed like a cow. His name is Mu. Seriously.
The jump itself was cool, though not what I was expecting. I was expecting a more stomach churning experience and some rollercoaster-ness, but freefall is eerily calm. Almost peaceful, except for the rush of wind in your ears. To be honest I didn't find it really exciting. I got more of a rush from ziplining. Anyhow, still a cool experience.
So that was the jump and kinda the end of the date. Nothing really more happened after that. We're still on friendly terms though. She wound up dating a friend of mine for a while, a super talkative head-in-the-clouds kind of guy, which I guess worked out since he did enough talking for the both of them.
To this day she doesn't remember anything about the jump.