Ask her out, then fark her. Dump her to the curb afterwards

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Money or no money, just don't put her under too much pressure. Don't put her in a position where she feels like she OWES you a favor or something. Sometimes you get lucky and the girls that feel obligated to repay you for kindness do so with sex or affection (I've had my share), but I do prefer it when the girl is diggin' it too, ya know
When brainstorming, if it FEELS like a bad idea, don't do it. You gotta play these things by feel.