As a 50 something gent, I’m old fashioned. I’d be expecting to pay, but would tend to gauge the level of angst in the lady if she offered to pay or go halves. You can usually tell if you’re out with someone with similar values.
Similarly, I’d not expect anything in return, never really understood that mentality - buy a girl a drink and expect something, wtf?seriously, if life that was that easy lol.
My old fashioned values probably don’t sit right with some feminists today, but as I’m off the market, having found my soul mate in the most alpha female going who respects and appreciates me, im not going to change.
Follow your instincts and gauge the guy, derive your opinion of his actions towards you, and how he treats others, and judge him based on his character. Forget what ‘society’ expects, that’s a spectrum ranging from nonsense to not valuing yourself, to being stuck up your own bum.
Good luck in your dating and I hope you find your soul mate.