A 67-year-old Florida man is facing multiple felony charges after deputies say he chased down his 21-year-old Tinder date, rammed her car into a utility pole, and held her friend at gunpoint when she tried to end their evening early.
David O’Brien of The Villages was arrested by Sumter County Sheriff’s deputies on July 22 and charged with four counts of aggravated battery and one count of aggravated assault with a deadly weapon. He was released after posting a $90,000 bond and is scheduled to appear in court on Aug. 14.
According to a probable cause arrest affidavit, O’Brien first matched with the 21-year-old woman on Tinder on June 27. Conversation picked up weeks later on July 12, when O’Brien told her he was “looking for a sugar baby” and offered $1,000 for each visit, along with dinner.
“I love to shop for you,” O’Brien allegedly texted her during their conversations.
The pair agreed to meet for dinner, and the woman had three friends drive her to the restaurant. Before eating, O’Brien took her to a lingerie store and purchased three items for her. During dinner, he handed her $600 cash.
The woman went back to O’Brien’s home after dinner, but according to the affidavit, she quickly began feeling “uncomfortable” and called her friends to come pick her up.
When her friends arrived, O’Brien grew angry and demanded his money back, telling her to “give the money back because that was not the agreement,” deputies wrote. The woman got into her friends’ car and drove off anyway.
Deputies say O’Brien then got into his Ford F-150 pickup truck and pursued the vehicle. When the cars reached a roundabout, O’Brien allegedly rammed the back of the victims’ car, sending it crashing into a pole.
Four victims were in the vehicle during the crash. Three of them immediately ran from the wrecked car. O’Brien allegedly pulled out a gun, approached a 22-year-old male passenger, and “told him to get on the ground, or he would kill him,” according to the affidavit.
The young man complied, but managed to run to safety when O’Brien became distracted. O’Brien returned to his truck as deputies arrived on the scene.
During an interview with investigators after receiving his Miranda rights, O’Brien confirmed he had been looking for a “sugar baby” arrangement, noting he had a similar arrangement in another state that “worked out perfectly for him.”
O’Brien told police that once his date asked to leave, he realized “things were not going to go as he had planned” and asked for his cash back. He claimed the woman promised to return the money outside, but instead jumped into her friends’ car and left.
Feeling “scammed,” O’Brien admitted to following the group, but told police the victims lost control of their own vehicle and crashed. He said he pulled his handgun to “control the situation” because he believed the car might have been stolen after the occupants ran, though he denied directly pointing the weapon at anyone.
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