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Money can buy almost anything — except love. But enormous wealth does not always come with common sense, and people looking to get their hands on someone else’s fortune know how to spot a wealthy target from a mile away, the New York Post reports.

Another alleged case has ended up in court. Widow Marianne Flippo has filed a lawsuit against 38-year-old Gregg Starr, accusing him of allegedly extracting $6 million from her.

Starr, who worked for the escort agency Cowboys4Angels, met Flippo after the death of her husband, Chad, a software developer who worked on the creation of Roblox. He died by suicide in 2024.

According to Flippo, Starr, who has undergone numerous plastic surgeries and became known for his piercing stare and sculpted physique, professed his love for her and then told her that, in order for them to be together, she would have to buy out his $10 million contract.

The lawsuit alleges that 49-year-old Flippo was staying at a Four Seasons hotel under the influence of alcohol and “several prescription medications” when she signed documents transferring millions of dollars to Starr.

He denies the allegations of coercion.

What actually happened will now be determined by the court. Psychiatrist David Puder, however, says that stories like these often revolve around vulnerable people.

“People who are after money look for someone with psychological needs and vulnerabilities. If you have enough money, you have a target on your back. The more money you have, the bigger the target,” he explains.

The very qualities that make someone a good partner can also make them an easy target: empathy, loyalty and the ability to form strong attachments. According to Puder, these traits can be exploited by people with what is known as the “dark tetrad” — a combination of narcissism, psychopathy, Machiavellianism and sadism.

A source for The Post who observed one such man in the western U.S. said he deliberately targets wealthy, single women, many of whom work in the technology industry.

“He’s relatively attractive, and his personality is so charming that women genuinely feel special. They walk into a bar, and he makes the woman the center of attention for the entire group.”

According to the source, the man decided long ago that he would never work and would live off women instead. They drive him around the country, pay for expensive hotels and cover other expenses.

One of his tactics is to suggest getting a dog, creating the impression of a family life and making it harder for the relationship to end. Another is to persuade his partner to open an investment account that he effectively controls himself.

“It’s all very deliberate. He’s incredibly calculating, very intelligent and understands psychological games extremely well,” the source said.

Such relationships can last anywhere from several months to several years. Another tactic, according to Puder, is so-called “love bombing,” in which a person is showered with attention and promises from the very beginning.

“When idealization becomes extremely intense from the start, the relationship can be perceived as the chance of a lifetime.” Against this backdrop, the psychiatrist explains, dopamine and oxytocin can intensify emotional attachment, while critical thinking may become weaker.

Even billionaires accustomed to tough negotiations and careful calculations in business are not immune to such situations.

Media mogul David Geffen, 83, whose fortune is estimated at $9 billion, became embroiled in a high-profile divorce from Donovan Michaels, whose real name is David Armstrong. After their split in 2025, Armstrong filed a lawsuit alleging that their first encounter was an intimate meeting for which Geffen paid him $10,000.

In court documents, Armstrong also claimed that Geffen demanded extreme sexual encounters and sought “complete domination” over a partner who was 50 years younger than him. Geffen’s lawyers accused the former porn actor of taking advantage of his husband’s generosity by spending money on luxury shopping, travel and OnlyFans subscriptions.

The two sides settled their disputes, and the terms of the agreements were not disclosed. Despite the disparity in their fortunes, the couple did not have a prenuptial agreement.

Another case involves California billionaire Stephen Cloobeck, 64, and 29-year-old Adva Lavi, a former Penthouse model and OnlyFans star who had previously been accused of defrauding wealthy men even before she met Cloobeck.

Lavi, also known as Mia Ventura, has pleaded not guilty to charges including grand theft, burglary and misuse of personal identifying information. Cloobeck repeatedly insisted that he knew her better than anyone and was helping her defend herself. The couple even planned to marry in Israel, but a judge did not allow Lavi to leave the United States.

Law enforcement officials have also said there may be additional cases involving Lavi in the U.S. and Europe and are investigating whether she may have given Cloobeck ketamine.

Despite this, a source close to the couple told The Post that Cloobeck “still cares about Adva.”

According to Puder, such behavior is not uncommon: people can return to relationships even after they believe their partner has taken advantage of them.

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