First of all, I just discovered this sub and I'm enjoying it a lot. The people here seem more inclined to give advice than most other RP-related boards.

Here it goes. I recently ran into a girl I had not seen in ages. We chatted it up and I took her number. Texted very briefly. I told her she was going for drinks with me a couple of days from now. I set that up at a bar near her place and she was into it, replying quickly and talking more than I was. She even mentioned how she lived alone in a big apartment. Seems good, doesn't it? The thing is that I'll probably have to change her perception of me completely in the span of that date, because she's seen me in fucking diapers. That's right, I'm trying to seal it with my old sitter. I'm now 22 and she's 28. Hadn't seen each other in a little over ten years, and she's grown to be a solid 7-8.

I'm not completely new to game. I'm relatively successful and it's not the biggest age gap I've ever dealt with, but the context is something new to me and would be quite a feat to accomplish. Any thoughts on how to overcome this?