I have dated multiple times in one week. Years ago as a 30 year old on a scholarship, looking for the right person for serious dating leading to marriage. I put it alll out there in an advert in a free local newspaper. Received 88 responses, talked to 15, dated 12, married one.
First dates were a mixture of breakfast, lunch, dinner, coffee because if a guy is interested he will make the second date before the first is over.
I started out with coffee and paid for myself because I didn’t want to feel obliged to continue or create a debt/credit relationship. Once I was seriously dating I turned down all others and my bf, now husband, took it in turns to pay or cook.
Its not awkward, to me, to pay for myself. However it is awkward to be with someone stingy who doesn’t offer to pay, or choose interesting things to do, or who is incapable of imagining hosting or treating. Because I didn’t want to be with someone charmless, dull, unimaginative, too focused on money, unable to host.
One of my dates with my lovely now husband of umpteen years was going to see Plan 9 From Outer Space the camp sci fi movie which was a cheap afternoon at a low rent bar with a small tv set up on the bar playing a cheap video of the film while we had s beer.
By the way my dh was the breadwinner for years until now when i started a new career and he retired. That worked for us because we love each other and the family we created so who did one kind of work and who did ghe other was not important.