Well the guy doesn't need to prove anything. Majority of people are judgy. But why limit your romantic chances. Why not something meaningless, e.g. Entrepreneur, I deal in classic cars.
Because both suggest a level of financial independence?
I've been on dates that have turned into wealth interviews after the initial breaking the ice chit chat. It's more common than you might think, especially when you get past middle-age.
When we first started dating (in our 30s), my now-wife thought I was broke as I was driving a 20 year-old, 100K+ mile Alfa Romeo. I loved the car; she just saw it as old and a little ratty.
That just filters out the blatent obvious gold diggers. The smarter, less obvious ones, who have googled your net worth are going to go undetected for way too long, and by then you're emotionally invested, and potentially married, possibly with kids. So pretending to be poor when you're happy with what you have, is not the worst strategy.
I would argue those games all very much involve competition. They all still involve winning/losing and skill testing, even if it just against yourself.
I think I'm a cynic. I always read things like this as, "Here's the problems you'd have if you won a bunch of money and this is how I would deal with them."