My dad knew a guy in the AF who did just that. He wanted to serve his country, so he signed up for a 4 yr rotation. Didn't tell very many that he was a trust fund baby. My dad was one of just a couple that knew. Lived on his military pay, drove an old beater. Met a young lady, started dating. She married him, right before he was scheduled to get out of the AF. She thought they were going to have to start their lives with nothing. They loaded up their belongings in the beater and off they went. He stops the car in front of this huge house and gets out. She thought he'd gotten a job as a gardener or something, working for the people who lived in the house. It took him a while to convince her that it was his parents' house and for reality to sink in.
There’s another tale of a billionaire who (like a surprising number of the super-rich) liked driving his ancient rusting truck and wearing flannel shirts. When he dropped into the town’s upscale car dealer to get a nice BMW or some such for his college-bound daughter, the staff ignored him. When he approached and asked for service, they told him “if you’re driving that old POS truck, you can’t afford our cars - beat it old man.” He left, had a cup of coffee at the diner across the street, and made two phone calls. Minutes later, the sales manager then went to the staff and told them “ya know that old guy you just kicked out? he just bought the dealership and fired you all.”
Don’t knock a guy for paying for a first date using a coupon.
Rich people don’t pay full price - that’s how they got rich.