One Florida resident’s attempt to find a companion on a dating app reportedly turned into a dramatic, dangerous scene involving a high-speed chase and a gunpoint standoff. David Allen O’Brien, 67, was arrested after he allegedly rammed a car carrying his date and her friends before threatening them with a firearm.
According to the New York Post, O’Brien matched with a woman on Tinder on July 12. He messaged her to say he was “looking for a sugar baby.” Per reports, the two eventually set a date for Tuesday evening. The arrangement, as noted by Villages News, included a promise of $1,000 for each visit, along with dinner. Per the NY Post, he also told her, “I love to show for you,” per the arrest report.
According to the outlet, the woman arrived for the date with three friends. They waited for her while she met O’Brien. The evening started with O’Brien giving her $200 and “took her to a lingerie store where she purchased 3 items.” Following the shopping trip, they went to dinner, where he reportedly handed her an additional $600. The pair then traveled to O’Brien’s $270,000 home, located on San Bernardo Road in The Villages retirement community.
Things changed once they reached the residence
According to Village News, the woman told deputies she “began to feel uncomfortable” while at the house. So she contacted her friends to come pick her up. When O’Brien realized she intended to leave, he allegedly demanded that she return the money he had given her. He allegedly told her, “that was not the agreement.”
The woman refused to hand the cash back and left the home to meet her friends, who were waiting nearby. Recently, the Deputy Assistant Secretary for Counterterrorism found herself under investigation after she was found on a Sugar Daddy website to fund her lavish lifestyle.
WFLA reported that O’Brien followed the group in his Ford F-150 pickup truck. The chase continued through The Villages until the vehicles reached a roundabout at the intersection of Buena Vista Boulevard and El Camino Real.
As he caught up to them. O’Brien purportedly rammed the back of the victims’ car, causing the vehicle to hit a pole. The arrest report stated that he then “came around again and hit the victims’ car once more causing it to become disabled.”
According to the NY Post, the woman and two of her friends managed to flee the scene on foot. However, O’Brien allegedly cornered one of the male friends by the car. According to the arrest report from the Sumter County Sheriff’s Office, “The defendant pointed his 22 semi-automatic Ruger at him and told him to get on the ground or he would kill him.”
Fearful for his life, the victim reportedly lay face down on the ground. However, he was able to escape when O’Brien became distracted. Per the outlet and arrest report, O’Brien allegedly attempted to find the other victims. In a different case, an Ohio doctor who posed as a sugar daddy for teens online was recently found dead. Unlike the cash O’Brien promised, the doctor allegedly gave out vape pens and petty cash.
Per the report, law enforcement officers received several 911 calls regarding the crash. When deputies arrived, Village News noted that they found O’Brien near his truck with the handgun still in his possession. Per WFLA, all four victims later spoke with deputies. They stated that they “were in fear for their lives” during the encounter.
NY Post noted that O’Brien was taken into custody and transported to the Sumter County Jail. He now faces one count of aggravated assault with a deadly weapon without the intent to kill and four counts of aggravated battery. O’Brien was eventually released Thursday afternoon on a $90,000 bond.
Published: Jul 25, 2026 12:46 pm