Inexplicably, sometimes gold diggers resort to blackmail.
The story goes something like this: rich guy (Dupont heir Stephen Dent) uses sugar daddy website for philandering, rich guy puts himself in compromising position (vis-à-vis his philandering), nefarious party extorts rich guy, long arm of the law eventually catches nefarious party: repeat until family, friends and coworkers are thoroughly embarrassed.
The New York Post (who really seems to love this puerile stuff, with the muckraking of the mighty and whatnot) goes on to say that Stephen Dent ended up being blackmailed a total of three times yet continued to use the popular rich dude – gold digger website to tickle some scratch he absolutely couldn't reach. Obviously, he's from the school of belief that lightning rarely strikes twice and never three times (rather than the school of fool me once, shame on you, fool me twice, shame on me, fool me three times, shame on my parents for feeding me lead paint chips as a kid). C'mon brah, the old honey trap has got to be the oldest trick in the book.
Obviously, anyone who would keep fishing from the same pond must have had his mind on something else when he kept on making the exact same mistake (or maybe he had so many good experiences that three bumps in the road were really just casualties of war). Either way, duder probably has a sex addiction (if there's such thing) or one of them there obsessive personalities. While rich doesn't equate to good decision-maker (or, clearly, happy), it does generally provide options and you'd think that someone with anything approaching Dent's fortune (like $100 million) would use a little more discretion when pulling undercover capers. Maybe the danger is what makes the whole thing worth trying. And maybe gold diggers wouldn't bat an eye at something that a more discreet individual would consider over the line (or charge extra for). Read: Why Powerful Men Cheat