How it usually starts
The money leak almost always starts with “impressing.” You don’t want to lose her to the guy who looks bigger, smoother, more established, so you go a little harder than you normally would. One upgraded dinner becomes the baseline. Then gifts show up early to “stand out.” Then trips start getting floated because they feel like a shortcut to closeness and a way to lock in the connection.
None of that automatically means you’re being used. The problem is what happens inside your head as it goes on: spending begins to feel like proof, and you start attaching unspoken expectations to it. You start thinking, “After all this, she knows I’m serious,” or “This should move things forward,” while she’s treating it like a lifestyle option she can accept without offering anything real back.
That’s how the fantasy starts charging interest.
The line you should actually watch
The clean divider isn’t the dollar amount. It’s whether your spending still feels like a choice.
If you spend and you genuinely feel good about it, you’re fine. If you spend and you feel that tight, irritated internal pressure afterward—the one that sounds like “I hope she appreciates this,” or “I hope this keeps her interested”—you’re drifting into a bad deal, even if you won’t admit it yet.
It gets obvious when money starts functioning like a loyalty test. She doesn’t always say it in a dramatic way; it can come out as “standards,” jokes, or little comments that carry a threat underneath. The message is that access to her depends on upgrades, and that the relationship is conditional on you paying past your comfort level. The moment you comply under pressure, you teach her that pushing your line works.