I read it as "she will become attracted to him because of this signaling".

Seems like such a shitty thing to say to someone.

The insinuation is, as his high-roller life elevates his social status, he becomes very attractive to her.

I think part of the "high-roller life" includes hiding the source (or obstructing) of your wealth. So I doubt that OP's SO will fall for it as she sees the source herself.

It would be like someone trying to impress someone with a fake Rolex that the other person knew was fake.

Money is money, and status is status, especially to women. You think even criminality changes that?

You know how many girls have said "I can't stand him" to my friends and then slept with me instead of them?

Come on guys get real. Women aren't angels - quite the opposite.