My last boyfriend, I think on our first date, we agreed to go halves, fine. Over the next few months it was always halves, apart from on my birthday when we got a burrito meal from a sort of kiosk/pop up van and drinks separately at a similar kiosk/drinks van - and I insisted he pay for all of this then. I was going to do the same for him on his birthday when it came around.
But from then on (he does work, does have money, but works on contracts in TV), it was either freebie dates - so film previews with canapes/free drinks, parties, or things where he didn't have to get his wallet out. It was when his housemate's wife (he rents out a room in his house to friends of his who stay over a few times a month when they need a room, also in the same industry) said something about "moths coming out of your wallet" and asked him when he was going to take me anywhere nice - it was always me suggesting places to go - that I thought, after a year of dating him, that he wouldn't get any better.
He had actually just offered that same month to buy me a Christmas present and named a price (I was quite surprised but impressed by that) he could afford but I think he was just tight generally, which is a real turnoff for me, especially when you don't have dependants and it's just you to think about.
I personally find it really icky when men or women depending on which sex you date don't offer to pay occasionally for you, whilst you're dating, not on every date, but at least sometimes. Generally I find, most men earn double or triple what women earn (gender pay gap?!) and have less outgoings when it comes to a date and preparing for them. What do men have to do, shave, shower and iron a shirt/t-shirt? Women spend far more, in general, on hair, makeup, outfit (am generalising here as not all women do this) for a date. I've never begrudged the extra expense though.
The absolute worst is men who expect sex or you to 'put out' after you've had a meal which they've said they'll pay for on a first date and have invited you on first (general dating etiquette is if a man asks for a first date, he pays for it all). I've known women who've used men for dates and got them to pay (can't say I've done this or if I have, it's been totally unintentional).
I've also had the card declined after you've tapped it a few times during the same day. This man should definitely have allowed you to have paid rather than assumed he was paying (but then wanting to claw back half of it). I'd be really turned off.
I've known men who've been 'poor', who've insisted on paying for a first date in full as it was manners, and didn't expect anything in return. Also, I tend to find (maybe true or not?!) stingy with money, stingy in the bed?!
I've also found out, it can be really tricky when properly dating men/women to work out the 'payment schedule' - e.g. if you go Dutch all the time, some of the time, do you let them get cinema tickets and you e.g. get drinks and popcorn [popcorn] etc?! Such a minefield...
Throw this one back and concentrate on the other guy!