@AmbiguityGreat post! It's okay it's short, you've given me enough to work with anyway ;) hehe.
It does remind a little of our own roleplay I agree hehe, so that's just awesome ;)
It would be fun to continue doing them, not too much though as I think it could drag out fast, but like once in a while we get into a game :)
Hmm, I'm not sure, it shouldn't take too long, but that's why I said that we could time skip instead of playing out all the games they play together before they meet up.
For example we could time skip now, up until the day where either of our character invites the other out. Or maybe it's not really a date-date as such, but more like, they both wanted to meet up and have talked about it for some time, and then they finally decide to meet somewhere :p