I can see it already. You're thinking to yourself "this isn't about money!!! I don't want to seem like a gold digger!"

And you're right. BUT DON'T hold that against yourself ONE bit. This was never about money for you. Don't even let him try to spin it that way. And trust me, he will spin it that way if it ever comes down to a shit fight.

And he 100% did use you.

So... I've been in similar situations. I started and sold a arbitrage company in college and came into a bunch of money and haven't needed to work since (I do though).

I still live someone normally/frugally after that. Studio apt, etc.

Dating wise, I don't ever talk about my financial situation with someone new. But after a year or two? 100% I would tell them. I'd also be clear early on that I want to keep finances separate/have a pre-nup if it ever came to it.

After a year or two is SUPER conservative.

But you've been with him for FOUR years and he's never brought it up????

And not only that, he doesn't PAY HIS SHARE?????????????? WTF?????????

So you've demonstrated that you'd be willing to provide for him... but he is not even CONSIDERING reciprocating.

Forget reciprocation, you had a financial emergency and he just SAT there quietly? Not even offering to help?

That's some serious red flags.

It's not even about the money. It's not even about trust at that point -- we're past htat. It's about being a selfish dickhead.

If he'd watch you selling your belongings to save your dog and remained completely disinterested... what would he do if YOU fell ill? If YOU ran into some hardships? And you're... thinking about marrying this person?