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Elderly Florida man faces charges after alleged ‘sugar baby’ dispute ends in car-ramming, gun threat: police

News RoomBy News RoomJuly 25, 2026No Comments3 Mins Read
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Elderly Florida man faces charges after alleged ‘sugar baby’ dispute ends in car-ramming, gun threat: police
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A 67-year-old man’s search for a “sugar baby” ended with him allegedly pointing a rifle at a 22-year-old after ramming a car into a telephone pole, according to his arrest report.

David Allen O’Brien, who lives in The Villages, a sprawling retirement community in central Florida, was arrested Tuesday on charges of aggravated assault after allegedly chasing down a 21-year-old woman he had paid in a “sugar baby” arrangement and ramming her car with his truck, according to the arrest report.

The arrest report details how O’Brien met the woman on the dating app Tinder and told her he was “looking for a sugar baby,” a romantic arrangement that typically involves an older man spending lavishly on a younger woman.

FLORIDA MAN WHO ALLEGEDLY LURED WOMEN WITH DATING APP COULD HAVE MORE VICTIMS: AUTHORITIES

The pair agreed to meet on July 21 and O’Brien told the woman that he would give her $1,000 “each visit… dinner and I love to shop for you,” according to the affidavit.

The woman showed up to dinner with three friends waiting in the car, according to the affidavit.

When she arrived, O’Brien gave the woman $200 and took her shopping for lingerie. They then went to dinner, where he gave her another $600. Afterward, they went back to his home where she “began to feel uncomfortable and contacted her friends to come pick her up,” the arrest report reads.

FLORIDA MAN WHO ALLEGEDLY LURED WOMEN WITH DATING APP COULD HAVE MORE VICTIMS: AUTHORITIES

“The defendant stated he began to massage [the woman’s] feet and she was on her phone the entire time. The defendant advised [the woman] went to the bathroom and when she came out she stated she was going to call an Uber to pick her up,” the report reads.

O’Brien then told the woman she “should give the money back because that was not the agreement,” the report reads. She got into her friends’ car, at which point O’Brien allegedly began chasing them in his Ford F-150 truck.

Ford F-150

When the four friends reached a traffic circle, O’Brien rammed their car with his truck, forcing it to crash into a telephone pole, according to the affidavit. Three of then fled their vehicles, but when the fourth, a 22-year-old male, attempted to leave, he was met with O’Brien allegedly pointing a gun in his face.

FLORIDA MAN WHO ALLEGEDLY LURED WOMEN WITH DATING APP COULD HAVE MORE VICTIMS: AUTHORITIES

“The defendant pointed his 22 semi-automatic Ruger at him and told him to get on the ground or he would kill him,” the arrest report read.

The man “was on the ground face down and noticed that the defendant was distracted so he was able to move to safety,” the report also read.

When police arrived on the scene, they found O’Brien at his truck with his weapon in possession, according to the arrest report.

O’Brien claimed the car he was chasing had its tail lights blacked out, a sign, to him, that meant he had been “scammed,” according to the arrest report.

Hands of anonymous woman browsing social media app on smartphone and typing heart emoji at night, surrounded by soft bokeh of urban lights. Fingers move on screen as warm city glow contrasts with cool device light. Subtle reflections highlight hands, capturing quiet moment of digital interaction in nighttime setting.

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O’Brien was charged with aggravated assault with a deadly weapon without the intent to kill and aggravated battery. He was transferred to Sumter County Jail “without incident,” per the arrest report.

His arraignment will take place on Aug. 14, according to Sumter County records.

Fox News Digital contacted the Sumter County Sheriff’s Office for additional details.

Read the full article here

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