David O'Brien wanted to find what he called a "sugar baby" on Tinder. Instead, the 67-year-old from The Villages is facing criminal charges after police say he chased down his date and her friends in his pickup truck, rammed their car into a pole, and pointed a gun at one of them.
Background
O'Brien matched with a 21-year-old woman on Tinder on June 27. According to a probable cause arrest affidavit from the Sumter County Sheriff's Office, there wasn't much conversation until July 12, when O'Brien informed her he was "looking for a sugar baby." The two exchanged numbers and began texting.
The defendant told the victim he would give her $1,000 each time they met, plus dinner. "I love to shop for you," O'Brien allegedly added in messages.
They agreed to meet at a local restaurant on July 27. The victim had three friends drive her to the dinner. O'Brien took her to a lingerie store, where he bought her three items, according to the affidavit. After dinner, he gave her $600.
Afterward, the two went back to O'Brien's home. That's when things took a turn. The victim told investigators she felt "uncomfortable" and asked that her friends come pick her up.
The Investigation
O'Brien allegedly demanded the money back because "that was not the agreement." The victim drove away with her three friends in their car, but O'Brien wasn't done.
"He began to chase them," according to the affidavit. When the victims reached a roundabout, O'Brien, driving his Ford F-150 pickup truck, "rammed the back" of their vehicle, causing it to slam into a pole.
Three of the victims fled on foot. That's when O'Brien allegedly pointed a gun at a 22-year-old man among the group and "told him to get on the ground or he would kill him."
The victim complied but managed to escape when he noticed O'Brien was distracted. Officers arrived as O'Brien walked back toward his truck.
"I love to shop for you," the defendant allegedly messaged his date before their meeting, according to the affidavit. "He said once his date asked to leave his home, he realized 'things were not going to go as he had planned' so he asked for his money back."
In an interview with investigators after receiving his Miranda rights, O'Brien confirmed he was looking for a "sugar baby" arrangement and would pay $1,000 per visit. He claimed he had a similar arrangement in another state that "worked out perfectly for him."
O'Brien told police he felt like he had been "scammed," which made him upset. He admitted to chasing the victims but said they lost control and crashed. The suspect claimed he believed the car was stolen because the victims got out and ran, so he pulled his gun to "control the situation" — though he denied pointing it at the male victim.
Key Takeaways
- David O'Brien, 67, of The Villages is facing four counts of aggravated battery and one count of aggravated assault with a deadly weapon
- He allegedly arranged a "sugar baby" meeting with a 21-year-old woman he met on Tinder who was more than four decades younger
- After she left his home feeling uncomfortable, O'Brien allegedly chased the victims in his Ford F-150 and rammed their car into a pole
- Police say he pointed a gun at a 22-year-old man among her group of friends and threatened to kill him
- Bond was set at $90,000; O'Brien has since posted bail
What's Next
O'Brien is next scheduled to appear in court on Aug. 14. The case remains under investigation by the Sumter County Sheriff's Office.