The wealthy widow of a pioneering Roblox programmer has accused a New York City escort of manipulating her into paying him $6 million so they could have an ‘exclusive’ relationship.

Marianne Flippo, 49, launched a lawsuit in Manhattan Supreme Court on Monday suing gigolo Greggory Starr, 38, for allegedly ‘taking advantage of a grieving and ailing widow to the tune of $5.95 million.’

The complaint, obtained by the Daily Mail, claims that Starr ‘enacted a ruthless plan to steal millions of dollars’ from Flippo while she was in a vulnerable state. 

Flippo said she was on strong opioids following surgery, and was still grieving the loss of her husband of 28 years, Roblox programmer Chad Flippo, when Starr convinced her to pay his agency millions of dollars to free him from his contract.  

The pair had struck up a relationship after Flippo paid Cowboys 4 Angels (C4A) male companion agency $27,000 for Starr’s translation services during a vacation to Italy in December 2024.

However, as their ‘love’ developed, Starr and his agent, Bridget Collins, told Flippo that she needed to pay $10 million in order for him to ‘escape’ his escort duties at C4A and become her exclusive boyfriend, according to the complaint. 

Flippo claimed in the lawsuit that she was ‘pressured by Starr and Collins’ to sign an ‘exit agreement’ to pay $5.95 million while ‘still emotionally lost due to the loss of her husband’ during a trip to Atlanta, Georgia in February this year. 

She claimed that they convinced her to drink booze before signing Starr’s ‘exit agreement’, and that she was impaired by ‘multiple prescription medications as well as five alcoholic drinks’ at the time. 

Marianne Flippo, 49, launched a lawsuit in Manhattan Supreme Court on Monday suing gigolo Greggory Starr, 38, for allegedly ‘taking advantage of a grieving and ailing widow to the tune of $5.95 million’. Flippo is pictured with Starr at a mansion party in New York City in December

New York City escort Greggory Starr, 38, has been sued by a grieving widow who claims he manipulated her into sending almost $6 million in funds to become her ‘exclusive’ boyfriend

Flippo’s lawyer, Larry Hutcher, also stated in an affirmation obtained by the Mail that she was suffering with ‘Stockholm syndrome’ and that Starr had a ‘Svengali-like control’ over her. 

The Daily Mail has reached out to Starr for his side of the story. He did not return phone calls or messages in time for publication. 

Flippo’s lawsuit outlines how she lost her childhood sweetheart and husband of almost three decades, Chad Flippo, ‘to the horrors of depression’ when he took his life on August 5, 2024.

Chad was ‘an extremely successful computer programmer who made a fortune programming for, as well as creating and patenting inventions related to, the popular online game Roblox’, and his widow inherited a ‘large fortune’ when he died, according to the complaint. 

However, his sudden passing ‘devastated Marianne and shattered her world’ and she ‘understandably struggled to cope with the loss’, according to the lawsuit. 

Her struggles were also ‘exacerbated’ by ‘Ehler-Danlos syndrome’, a disease which impacts the body’s connective tissues and limits life expectancy to around 50 years old. It also increases sensitivity to alcohol and medications.

Four months after her husband passed, Flippo decided to take a trip to Italy but was ‘nervous about traveling internationally’, according to her complaint. 

One of Chad’s former colleagues reached out to C4A on her behalf, and the agency paired her with Starr, an Italian speaker who could ‘assist her on the trip’. 

Flippo said she was not aware that C4A was an escort service at the time, and she hired Starr ‘purely for assistance on her trip’, according to the complaint. 

New York City escort Greggory Starr, 38, has been sued by a grieving widow who claims he manipulated her into sending almost $6 million in funds to become her ‘exclusive’ boyfriend

Flippo and Starr are pictured with a friend at a New York City mansion party in December 2025

‘During the trip, Starr had his own room and while he did make advances to Marianne she turned him down because she was still mourning Chad,’ the lawsuit states. 

Flippo paid C4A $27,000 for Starr’s services on the trip, and did not have any contact with him after returning home until C4A began calling her, according to the complaint. 

The widow claims that C4A employees including Collins started calling her to tell her that ‘Starr missed her and wanted to talk to her’. 

Flippo agreed to meet with Starr, and, sensing her ‘vulnerability and knowing of her wealth’, he ‘began to worm his way into her life’, the complaint claims. 

‘After Starr firmly had Marianne hooked, he convinced her to continue paying C4A to spend more time with him,’ the lawsuit alleges. 

He then ‘insisted’ that she wire C4A $150,000 so that he could date her ‘exclusively’. Flippo said she was ‘swept up by Starr’s whirlwind of affection’ and ‘agreed to this contract’. 

As their relationship developed, Starr ‘further ingratiated himself into Marianne’s life and psyche, and ultimately made her dependent on him’, the complaint alleges. 

Meanwhile, Collins also ‘wormed her way into Marianne’s life and convinced her that they were friends’ in order to ‘manipulate’ her, according to the complaint. 

Flippo claimed that Starr ‘began acting oddly’ in the summer of 2025, and admitted that he had been seeing an ex-girlfriend, prompting her to break up with him on October 1.

‘This should have been the end of the situation, but C4A and Starr would not let Marianne and her money go,’ her complaint alleges. 

Collins and her assistant ‘repeatedly’ contacted Flippo and tried to convince her to meet with Starr, the lawsuit claims. They told her that ‘Starr loved her, was sorry, and wanted to get back together with her’, per the complaint. 

The Daily Mail has reached out to Starr for his side of the story. He did not return phone calls or messages in time for publication. He is shown in a photograph from his Instagram account

New York City escort Greggory Starr, 38, has been sued by a grieving widow who claims he manipulated her into sending almost $6 million in funds to become her ‘exclusive’ boyfriend

The widow claims that Starr ‘wove a web of emotional manipulation’ which ‘ensnared’ her, ‘with the goal of taking her money’. 

Flippo’s lawsuit adds that while ‘still in a vulnerable state’, she ‘eventually gave in and agreed to meet with Starr’ in November 2025, when the escort allegedly ‘forced her to get back together with him’ through manipulation. 

Starr moved into her apartment on December 1, 2025, and asked her to sign another contract with C4A so that they could be together ‘full time’, per the complaint. 

Flippo said she wired $368,000 to be with Starr exclusively from this date through May 2026. 

In early 2026, she traveled to Los Angeles for surgery, and in the aftermath, she had to take strong drugs, including gabapentin and codeine, a narcotic. 

Combined with her Ehler-Danlos syndrome, this put her in a ‘compromised mental state’, according to the complaint. 

She also suffered ‘from a severe infection in her arms’ which required even more medication, the lawsuit states. 

It was during this ‘time of vulnerability’ that Collins told Flippo that it would take $10 million to free Starr from his contract, and that she was his ‘only way of escaping C4A’.

Flippo and Starr traveled to Atlanta to visit Starr’s mother in February, and ‘Collins and her assistant suddenly appeared’ on the trip saying they had come to support the escort, according to the complaint. 

The apparent couple went for lunch with Collins and her assistant, and they ‘insisted that Marianne drink alcoholic beverages’, the complaint alleges. 

The Daily Mail has reached out to Starr for his side of the story. He did not return phone calls or messages in time for publication. He is shown in a photograph from his Instagram account

Flippo has sued Starr for allegedly ‘taking advantage of a grieving and ailing widow to the tune of $5.95 million’. Flippo is pictured with Starr at a mansion party in New York City in December

‘Starr and Collins were aware of the medication that Marianne was on and that she should not be drinking, but continued to pressure Marriane to drink and even ordered shots for the table,’ the lawsuit claims. 

‘Only after Marianne had had several drinks did Starr and Collins reveal the $10 million Exit Agreement.’

Flippo said the drinks interacted with her condition to ‘render her mentally incapacitated’, and Starr and Collins were able to ’emotionally manipulate’ her into signing the agreement, according to the complaint. 

‘Marianne only signed the agreement because she was not in her right mind, due to the influence of her medication, alcohol and the tremendous coercive pressure she was put under,’ the filing states. 

However, Flippo’s bank, JP Morgan Chase, recalled the $10 million transfer believing it was part of a scam. The same thing happened when she tried to use her Westpac card. 

Starr ‘insisted’ that she open a Charles Schwab bank account which would allow her to transfer the funds, and she ‘made a series of transfers in May and June of 2026 totaling $5.95 million’, the complaint states. 

Flippo hired New York attorney Larry Hutcher, and ‘realized that Starr is a fraudster who shamelessly exploited her during the lowest period of her life’, according to her court filing. 

Her lawsuit claims that the $10 million was never needed to free Starr from his contract, and it was all part of an elaborate scam. 

The filing requests the voiding of her ‘Exit Agreement’ and for Starr and C4A to return the $5.95 million to Flippo. 

The Daily Mail has reached out to Starr, Collins, and Flippo’s lawyers for comment.