I mean, it completely depends on the person and stuff ...
I have never been on a single date, so I have absolutely no clue, but here is what I imagine:
In general: First date I would prefer something noncommittal like just going for some coffee or ice cream. If you don't like the person you don't have to spend too much time and chances are she won't like me anyway. Additionally, I would like to have someone who really likes me and not the money, and some girls just want to get dinner, so I would like to exclude that possibility.
I would just talk about normal stuff - what music/games/movies she likes, whether she has some hobbies and what she does in the spare time. The goal would be to find out which activities you could do together, so that you can do that stuff on the next date.
I think I would wear some a business casual shirt and a nice jean, but it completely depends on where the date is. If it would be in a nice restaurant, I would likely have to wear a suit.
I have absolutely no clue how to flirt. Probably I would try to just focus on things we could do together and imagine how nice it would be? I guess I would also try to find something nice about her, tell her compliments and then maybe ask a follow-up question (But this also sounds really stupid in my head ... like for example why would I be interested in make-up? That sounds like I just would need the information for someone else? And it would also make her expect me to buy her this e.g. lipstick, but idk ... ok, maybe no follow-up questions for that)
I would say the initial planned date duration should be 30 min - 1 hour, but with the option to "extend". Maybe I should secretly make a plan to have some nice restaurants and some other spare time activities (like a museum ... but depends on what she likes) near the coffee shop. Then I could just propose her, if I think it worked really well, to "spontaneously" invite her first to the museum and then to the restaurant nearby. But again, never went on a date, so probably this doesn't work.
The best case scenario is that during the date we find out an activity we can do in common, so the hope would be to agree on an activity in general, but leave details open. Then we can research possible venues and discuss details later.
But honestly, I think this forum is the absolute worst place to ask for dating advice?
