JULY 23--A “sugar baby” arrangement went sour when a young woman who apparently wanted nothing to do with the string attached fled the home of a Florida Man who then gave chase in his truck, rammed into her vehicle, and pulled a gun on her friend, police report.

According to investigators, David O’Brien, 67, met the woman this month on the Tinder dating app. During a subsequent exchange of messages, O’Brien explained that he was “looking for a sugar baby” and would pay “$1000 each visit...dinner and I love to shop for you.”

O’Brien and the “sugar baby” agreed to meet for a meal Tuesday evening. The woman was driven to the July 21 date by three of her friends.

O’Brien, according to an arrest report, gave the woman $200 and “took her to a lingerie store where she purchased 3 items.” After O’Brien provided the woman with another $600 at the restaurant, the pair went back to his residence in The Villages retirement community (which O’Brien purchased in April for $270,000).

The woman told cops that she “began to feel uncomfortable” in O’Brien’s home, and “contacted her friends to come pick her up.”

With his “sugar baby” fixing to depart, O’Brien told her that she “should give the money back because that was not the agreement.” Declining the refund request, the woman left the property and “got into the car with her friends and left the area,” cops say.

O’Brien then jumped into his Ford F-150 pickup and “began to chase the 4 victims.” He subsequently rammed into their vehicle at a traffic circle, causing it to strike a pole. He then allegedly “came around again and hit the victims’ car once more causing it to become disabled.”

While the woman and two of her friends fled, a male occupant of the car was confronted by O’Brien, who allegedly “pointed his .22 semi-automatic Ruger at him and told him to get on the ground or he would kill him.” Eventually, O’Brien became distracted, allowing the victim--who told cops he thought he was going to be shot--to run away.

“The defendant then attempted to locate the other victims briefly until he heard law enforcement arriving,” the report states. When deputies arrived at the scene, O’Brien was “at his F150 with the gun in his possession.” After being read his rights, O’Brien agreed to speak with a responding officer (though the substance of his remarks have been redacted from the document released by police).

The woman and her three friends, cops reported, all “stated that they were in fear for their lives.”

Seen above, O’Brien was arrested on five felony charges: aggravated assault with a deadly weapon and four counts of aggravated battery. He is being held in lieu of $90,000 bond in the Sumter County jail. (2 pages)