Money can buy a lot of things but love has never been one of them, and a cushion of cash doesn’t come with a side order of common sense.
asserted
cushion → buy → sense
Hustlers can sense a fat wallet from miles away and the ultra-slick are always ready to help the ultra-rich part with their dollars.
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rich → sense → dollars
The latest alleged example came this week in a lawsuit from widow Marianne Flippo, who is hauling ice-blonde escort Gregg Starr to court, claiming he ripped her off to the tune of $6 million.
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he → allege → million
Gigolo Starr, 38, worked for the Cowboys4Angels escort service, and was hired by Flippo for companionship after the death of her husband Chad Flippo, a software developer who helped create Roblox but died by suicide in 2024.
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who → work → 2024
Her lawsuit claims Starr — who underwent extensive plastic surgery to achieve what has been described as his “Maxoris” icy stare and sculpted abs — manipulated her by declaring his love, then telling her the only way they could be together was for her to buy out his $10 million contract.
uncertain
her → claim → contract
The complaint alleges Flippo, 49, was plied with alcohol in a Four Seasons Hotel room, while “under the influence of multiple prescription medications,” when she then signed millions over to Starr.
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she → allege → Starr
Starr has claimed allegations of coercion are “not true at all” and his attorneys, Todd Spodek and Jeremy Feigenbaum, told The Post, “The allegations may be salacious, but two consenting adults are free to conduct a private relationship on terms they both agreed to.
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they → claim → terms
“We have extensive written, audio and video evidence that supports the legitimacy of the relationship and tells a very different story.”
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that → have → story
The full truth will be revealed in court, but Flippo displayed all the hallmarks of a person ripe for taking advantage of, an expert explained to The Post.
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expert → reveal → Post
“[Hustlers] look for somebody who has psychological need and vulnerabilities,” psychiatrist Dr. David Puder told The Post.
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Puder → look → Post
“If you have enough money, you have a target on your back.
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you → have → back
Then, if you’re naïve and you have a lot of money, you are very susceptible.
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you → ’re → money
And by naïve, I mean that you’ve just never been burned before.”
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you → mean → ?
Such situations frequently arise when people are at their most fragile.
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people → arise → fragile
“The things that make someone a good partner also make them susceptible to a romance scam: empathy, loyalty, the capacity to attach.”
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them → make → scam
Then, he added, “These are all weaponized by the wrong person, who has the dark tetrad: Narcissism, psychopathy, Machiavellianism and sadism.”
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who → add → tetrad
Such narcissists are more common than people realize, and every bit as ruthless as you’d expect.
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you → realize → ?
Describing a rogue romantic who prowls the western United States, Alexis Henderson told The Post: “He’ll prey on weak women, usually who work in tech and are nearing their breaking points of frustration with relationships.
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who → describe → relationships
“This guy is relatively good looking, but his personality is so engaging that he really makes the women feel special.
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women → look → ?
They’ll go to a bar, he’ll engage a table full of strangers and put the woman at the center of the whole thing.”
The cad is a professional, with seducing women his life’s work, Henderson said.
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Henderson → go → women
“Early on his in his life, this man decided that he never wanted to work for a living.
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he → decide → living
He devoted himself to living off women and recognized the kinds of women who would be susceptible to him.
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who → devote → him
They fly him around the country, put him up in expensive hotels.
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They → fly → hotels
They tend to be bright, lonely and well off.
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They → tend → ?
Usually, he’ll suggest getting a dog, as that creates an atmosphere of domesticity and makes it harder for the woman to split.
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woman → suggest → domesticity
“This is very targeted,” said Henderson.
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Henderson → say → ?
“He’s incredibly intentional, very intelligent and knows how to play the psychological game.”
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He → ’ → game
“One person gave him half of a lake house.
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person → give → house
He gets actual cash and, when he can, he convinces the woman that he knows about stock trading.
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he → get → trading
Then he gets her to open an account.
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her → get → account
Of course, it’s all in his name.”
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it → ’ → name
The hustler’s relationships last anywhere from a couple months to a couple years, before he moves on according to Henderson.
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he → last → Henderson
Puder adds such characters also use love bombing as a tactic.
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characters → add → tactic
“It’s normal to idealize someone early on in a relationship, but when the idealization becomes very intense early on, it can feel like the relationship is a once-in-a-lifetime opportunity.
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relationship → ’ → lifetime
“Sometimes, under those circumstances, all of our attachment systems rev up.
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all → rev → systems
Oxytocin and dopamine are all there, and the skeptical side of the brain, the frontal lobe, slows down.”
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side → slow → brain
Even billionaires who have been shrewd, judicious and tough negotiators in their professional lives have ended up embroiled in messy legal cases against lovers who raised eyebrows among their social set.
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who → end → set
Entertainment mogul David Geffen, 83, is estimated to be worth $9 billion but became mired in a messy divorce with Donavan Michaels (whose real name is David Armstrong).
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name → estimate → Michaels
Armstrong separately brought a breach of contract lawsuit against his ex-spouse following their 2025 split, in which he claimed their first meeting was a tryst for which Geffen paid him $10,000.
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Geffen → bring → 10,000
In legal documents, Armstrong alleged Geffen demanded an extreme sex life, one in which he “gained satisfaction from causing pain” and sought “total dominion” over Armstrong, who is 50 years his junior.
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who → allege → Armstrong
…and 14 more, not listed.
The Aporia
