Widow Sues Escort for $6 Million, Alleging Romance Scam

A New York widow has filed a $6 million lawsuit against a male escort, alleging he scammed her out of money by exploiting her grief after the death of her husband. Marianne Flippo claims Gregg Starr, who worked for the escort service Cowboys4Angels, hired for companionship following the 2024 death of her husband, Chad Flippo, a software developer credited with co-creating Roblox. The lawsuit asserts Starr manipulated Flippo, then 49, into believing they could be together only if she bought out his $10 million contract. According to the complaint, this occurred in a hotel room while Flippo was allegedly under the influence of alcohol and prescription medication.

Starr, 38, who reportedly underwent extensive plastic surgery to achieve a specific aesthetic, has denied the allegations through his attorneys. Todd Spodek and Jeremy Feigenbaum stated, "The allegations may be salacious, but two consenting adults are free to conduct a private relationship on terms they both agreed to. We have extensive written, audio and video evidence that supports the legitimacy of the relationship and tells a very different story."

Psychiatrists suggest that individuals with wealth, particularly those experiencing emotional vulnerability, can become targets for such scams. Dr. David Puder explained that scammers often seek out those with psychological needs and vulnerabilities. "If you have enough money, you have a target on your back," Puder told The Post. "And the more money, the bigger the target. Then, if you’re naïve and you have a lot of money, you are very susceptible."

These situations often arise during periods of fragility. Puder noted that qualities like empathy and loyalty, which make someone a good partner, can also make them susceptible to scams when "weaponized by the wrong person, who has the dark tetrad: Narcissism, psychopathy, Machiavellianism and sadism."

Another individual, Alexis Henderson, described a romantic predator operating in the western United States who preys on women, often those in high-stress tech careers. "He’ll prey on weak women, usually who work in tech and are nearing their breaking points of frustration with relationships," Henderson said. This individual is described as good-looking with an engaging personality designed to make women feel special. Henderson added that such individuals often decide early in life to live off women and identify susceptible targets, who then fund their lavish lifestyles.

Tactics employed can include "love bombing," where idealization of a partner becomes intensely early in a relationship, creating a sense of a unique opportunity. This can accelerate the release of bonding hormones like oxytocin and dopamine, potentially slowing down critical thinking.

The article also points to other high-profile cases involving wealthy individuals and their romantic partners. Entertainment mogul David Geffen, estimated to be worth $9 billion, was involved in a contentious divorce with Donavan Michaels (David Armstrong), who alleged extreme demands and control. Their cases were settled out of court. In another instance, billionaire businessman Stephen Cloobeck was involved with Adva Lavie, who has faced felony charges for allegedly scamming wealthy men. Lavie has pleaded not guilty to charges including grand theft and unauthorized use of personal information, and authorities are investigating further potential cases involving her across multiple jurisdictions. Despite these legal entanglements, a source close to Cloobeck indicated he still cared for Lavie.

These narratives illustrate a recurring pattern where individuals, despite their financial success and professional acumen, can become vulnerable to exploitation in their personal relationships, often when they are at an emotional low point.