A 49-year-old widow who lost her husband to suicide is now suing the male escort she hired for companionship, claiming he manipulated her into handing over $6 million, and her case is far from the only one exposing how predatory romancers target the wealthy.
Marianne Flippo filed suit this week against Gregg Starr, a 38-year-old escort employed by a service called Cowboys4Angels, alleging he declared his love for her and then told her the only way they could be together was for her to buy out his $10 million contract. Flippo's husband, Chad Flippo, a software developer who helped create Roblox, died by suicide in 2024. She hired Starr for companionship in the aftermath, the New York Post reported.
The complaint alleges Flippo signed over millions while inside a Four Seasons Hotel room, where she was allegedly plied with alcohol while already under the influence of multiple prescription medications. The total she claims to have transferred to Starr: approximately $6 million.
Starr denies the allegations. His attorneys, Todd Spodek and Jeremy Feigenbaum, issued a joint statement to the Post:
"The allegations may be salacious, but two consenting adults are free to conduct a private relationship on terms they both agreed to."
They added that they possess "extensive written, audio and video evidence that supports the legitimacy of the relationship and tells a very different story." Starr himself called the coercion claims "not true at all."
Flippo's case fits a pattern that psychiatrist Dr. David Puder described in blunt terms. Predatory romancers, he told the Post, zero in on emotional vulnerability, not financial carelessness.
"If you have enough money, you have a target on your back. And the more money, the bigger the target. Then, if you're naïve and you have a lot of money, you are very susceptible. And by naïve, I mean that you've just never been burned before."
Puder said the same traits that make someone a good romantic partner, empathy, loyalty, the capacity to attach, are exactly what a skilled manipulator exploits. He described the manipulator's psychological profile as the "dark tetrad: Narcissism, psychopathy, Machiavellianism, and sadism."
The early stages of these relationships, Puder explained, produce a neurochemical fog. Intense idealization early on can feel like a once-in-a-lifetime opportunity. Oxytocin and dopamine flood the brain while the frontal lobe, the skeptical, reasoning part, slows down. The mark doesn't feel like a mark. They feel like they're in love.
Romance fraud is not limited to escorts targeting widows. Six Nigerian nationals were recently extradited to the U.S. for allegedly swindling American women out of $6 million through online schemes, the same dollar figure Flippo claims she lost, though the tactics differed.
The Post also profiled an unnamed man operating across the western United States who has turned romantic manipulation into what amounts to a full-time occupation. A source familiar with his methods described a deliberate, patient approach.
"Early on in his life, this man decided that he never wanted to work for a living. He devoted himself to living off women and recognized the kinds of women who would be susceptible to him. They fly him around the country, put him up in expensive hotels. They tend to be bright, lonely and well off."
The source said the man specifically targets women in the technology industry who are "nearing their breaking points of frustration with relationships." He is described as relatively good-looking but primarily effective because of his personality, at a bar, he will engage a table full of strangers and put the woman at the center of it all, making her feel special.
The payoffs are concrete. One woman gave him half of a lake house. He collects cash. When possible, he convinces women to open stock trading accounts, all in his name. The source called his approach "very targeted" and "incredibly intentional."
His relationships typically last months to years before he moves on to the next target. Tools now exist that could help potential victims, a new background-check service for online daters lets users vet matches for criminal records and hidden red flags, but people in the grip of early infatuation rarely think to use them.
Even a net worth of $9 billion did not protect entertainment mogul David Geffen, 83, from a costly and embarrassing entanglement. Geffen married Donavan Michaels, whose real name is David Armstrong, a former go-go dancer and adult film performer 50 years his junior, without a prenuptial agreement. The marriage lasted less than two years before the couple split in 2025.
Armstrong then filed a breach of contract lawsuit against Geffen. In legal filings, Armstrong alleged their first meeting was a tryst for which Geffen paid him $10,000. He further alleged that Geffen demanded an extreme sex life, one in which he "gained satisfaction from causing pain" and sought "total dominion" over Armstrong.
Geffen's attorneys fired back, accusing Armstrong of exploiting his husband's generosity with "wild shopping sprees, lavish trips and OnlyFans subscriptions." Both the divorce and the breach of contract lawsuit were eventually settled. The terms remain private.
In an unusual twist, Armstrong told the Post that the two have since reconciled, at least as friends. Geffen reunited with Armstrong on his yacht after the divorce.
"David and I are still good friends to this day. He's done a lot of great things in my life. There is real love in this world."
Whether that statement reflects genuine affection or a carefully maintained financial relationship is a question the settlement's sealed terms will never answer.
The most legally serious case involves Adva Lavie, a 29-year-old Israeli native also known as Mia Ventura, a former Penthouse Pet and prominent OnlyFans personality. Lavie was criminally charged with allegedly romance-scamming wealthy men before she met California billionaire Stephen Cloobeck, 64.
She pleaded not guilty to felony counts of grand theft, burglary, and unauthorized use of personal identifying information, charges that, in plain terms, allege she stole from her romantic targets and used their personal data without permission. Despite the pending charges, Cloobeck maintained he knew Lavie better than anyone and planned to marry her in Israel.
A judge blocked the wedding by denying Lavie permission to leave the United States. She then ditched her ankle monitor. Her bail was revoked. She is currently in custody awaiting trial.
Authorities have said they are investigating further potential cases involving Lavie in Hermosa Beach, California, as well as in Nevada, Florida, Italy, and France. Police are also investigating whether Lavie had been drugging Cloobeck with ketamine. A person close to Cloobeck told the Post he remained friendly with his former fiancée and "still cares about Adva."
That a billionaire businessman could watch his fiancée face felony fraud charges, flee her ankle monitor, and sit in a jail cell, and still profess concern for her, illustrates exactly the dynamic Dr. Puder described. The attachment system overrides the reasoning brain. Loyalty becomes a liability.
One woman who encountered a different kind of romance fraud, a man posing as an NFL player to swindle women, said she spotted the deception early because it felt "too good to be true." Not everyone has that instinct, and the cases piling up in courtrooms suggest that wealth, grief, and loneliness can override it entirely.
The common thread across these cases is not greed on the part of the victims. It is need. Marianne Flippo had just lost her husband. The women targeted by the unnamed predator in the West were lonely and frustrated. Cloobeck, by all accounts, genuinely wanted a partner. Even Geffen, worth $9 billion, married a man decades his junior without basic legal protections.
Dr. Puder's clinical framing cuts through the tabloid surface of these stories. The qualities society encourages, openness, trust, the willingness to love again after loss, are precisely the vulnerabilities that predatory individuals weaponize. And the legal system, designed to adjudicate disputes between parties who dealt at arm's length, struggles with relationships where the manipulation was the relationship.
Starr's attorneys insist their client's relationship with Flippo was consensual and legitimate. Lavie has pleaded not guilty. The unnamed predator in the western U.S. has apparently never been charged with anything. These cases will play out in courtrooms and, in some instances, may never produce a clear legal verdict.
But the pattern is unmistakable. And the people left holding the bill are the ones who made the mistake of trusting someone who had already decided, long before the first date, exactly how much that trust was worth.
