All but one date I initiated, one girl messaged me spontaneously to go out that same evening.

I've generally paid for everything, and have taken the initiative to do so so there was no awkwardness around that. I'm personally more comfortable / feels more natural if I'm paying for most of the early dates. Most first dates were just coffee/boba so nothing too expensive either. A few dates were "two things" (dinner + drinks, activity + drinks etc) and all but one girl offered to pay for the second thing after I paid for the first.

Four special cases here:

• The girl who invited me out, we just got boba, I paid.

• One girl on a second date we cooked together, I got the ingredients but she brought a small dessert.

• One girl on the second date offered to split the bill on brunch but I declined (warmly, "oh no don't worry I got it :)" type rather than "no I will pay!" haha) and she got the boba after.

• One girl we got dinner and then went for ice cream for the first date (my plan), I paid for dinner then was kinda expecting her to jump in / offer to get the ice cream but she didn't. The second date we did an activity, got a drink at the bar attached to the activity, and then got dinner (my plan again, dinner was kinda spontaneous). After the activity + drink, I'd spent a total of ~ $120 over the two dates so far, so I expected her to offer to pay for or split dinner but we ended up splitting dinner without explicitly discussing it because the restaurant had one of those "order and pay all on your phone even though you are eating in" ordering systems. It's strange also because she definitely makes the most money, by a significant margin, out of all the girls I've gone out with (experienced software engineer in fintech). If we go on future dates I'll probably suggest free activities. But of the three second dates she's also the person I'm least interested in so might not even bother.