Tinder date gone wrong: The Villages man held woman's friend at gunpoint in money dispute, deputies say

SUMTER COUNTY, Fla. - A woman's Tinder date turned near-deadly when her date allegedly chased her and her friends on the road, rammed their vehicle into a pole and held a man at gunpoint, authorities said. 

Now, The Villages resident, David O'Brien, 67, is released on bond after being charged with aggravated assault with a deadly weapon without the intent to kill and four counts of aggravated battery. 

‘Looking for a sugar baby’ 

What we know:

"Looking for a sugar baby." That's how a Tinder conversation between the woman and O'Brien allegedly began on July 12 – one week before the incident. The woman showed detectives the message chain and said she continued to text O'Brien before agreeing to meet up on the evening of July 21. 

O'Brien reportedly told her he would give her "$1,000 each visit … dinner and I love to shop for you," a Sumter County arrest report said. 

The woman's three friends – who are also listed as victims in this incident – drove her to a restaurant on July 21 to meet O'Brien. Details in the arrest report reveal that O'Brien gave the woman $200 and took her to a lingerie store where she bought three items and gave her $600 for dinner. 

Uncomfortable date escalates to pursuit

When the woman went with O'Brien to his home in The Villages, she began to feel uncomfortable and asked her friend to pick her up, the report said. 

O'Brien demanded his money back, saying that wasn't the agreement between them, deputies said. 

When the woman got into a car with the three friends, O'Brien got into his vehicle and chased after them, the sheriff's office said. 

Suspect threatened to kill victim: Deputies

As the vehicles reached a roundabout in the area of Buena Vista Blvd and El Camino Real, O'Brien rammed the back of the friend's car – causing them to crash into a pole, the sheriff's office said. O'Brien crashed into their vehicle a second time, disabling it, the report said. 

All four victims scrambled out of the wreck. Three of them ran away, while O'Brien pointed a gun at the fourth victim, ordering him to get face down on the ground or be killed, the affidavit said.

While pinned on the ground, the victim noticed O'Brien was temporarily distracted and managed to crawl away to safety, the sheriff's office said. 

When deputies responded to the scene early July 22 after 91 calls, all four victims told authorities they feared for their lives, the report said. The man held at gunpoint told deputies he thought O'Brien was going to shoot him, the sheriff's office said. 

O'Brien was transported to the Sumter County Jail without incident.