Florida Man David O'Brien Charged After Tinder Date Leads to Gunpoint Chase

David O'Brien, a 67‑year‑old resident of The Villages, Florida, was arrested and released on bond after a violent confrontation stemming from a paid Tinder arrangement. According to authorities, O'Brien gave the woman $800, took her shopping, and later demanded the money back when she tried to leave, prompting a pursuit in which he rammed a Ford F‑150 belonging to the woman's friends into a pole twice.

During the incident O'Brien allegedly pointed a .22 Ruger at one victim, threatening lethal force before the victim escaped. Police found O'Brien still holding the firearm when they arrived. He faces one count of aggravated assault with a deadly weapon and four counts of aggravated battery, with a $90,000 bond set.

The case was reported by Sumter County officials, who said all four victims feared for their lives and described the incident as a “sugar‑baby” dispute that escalated into a near‑deadly road chase.