“We should work on fixing the single part of that section 😏”

Yeah definitely decaf for night dates. You don’t even have to specify unless they ask or bring it up

I think you could definitely give it another shot since she’s receptive to it, but when the time comes to “close” try and get a solid answer on where she stands with the two of you.
If she’s into the other guy, cut your losses and move on. If she’s into you, escalate from there.
More specifically, I think you gotta go for a kiss when you think the time is right. I think it would be better to know where you’re at then getting led along

I think you could also benefit from taking face pics at a slight angle, you have a pretty square jaw so straight on pics aren’t as flattering