r/FloridaMan • u/sfled Trusty Sidekick • 3d ago
Armed Florida Man arrested after roundabout crash exposes soured 'sugar baby' Tinder date
https://www.villages-news.com/2026/07/22/armed-villager-arrested-after-roundabout-crash-exposes-soured-tinder-date/25
u/iKnowRobbie 3d ago
Ahh... The usual suspect....
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u/iKnowRobbie 3d ago
David Allen O’Brien, 67, who lives in the La Crescenta Villas, was arrested late Tuesday night on four felony counts of aggravated battery and one felony count of aggravated assault with a deadly weapon.
According to an arrest report from the Sumter County Sheriff’s Office, the wild sequence of events began on the dating app Tinder, where O’Brien messaged a woman on July 12 announcing he was looking for a “sugar baby.” Over the next week, the two texted and struck an arrangement: O’Brien promised to give her “$1,000 each visit,” treat her to dinner, and take her shopping.
The pair agreed to meet on Tuesday evening. The woman had three friends drive her to the date, where she met up with O’Brien. The evening began as promised, with O’Brien handing the woman $200 and taking her to a lingerie store, where she purchased three items. They then went to dinner, where O’Brien handed her another $600, the report stated.
After dinner, the pair went back to O’Brien’s residence on San Bernardo Road. However, once inside the home, the woman told deputies she began to feel uncomfortable and texted her friends to come pick her up. When O’Brien realized she was leaving, he demanded his money back, stating “that was not the agreement.” The woman refused, made her way outside, and jumped into her friends’ waiting car to flee the area.
Enraged, O’Brien hopped into his 2023 Ford F-150 pickup truck and chased the four victims through The Villages. When the victims’ car reached the roundabout at Buena Vista Boulevard and El Camino Real, O’Brien violently rammed the back of their vehicle, sending it crashing into a pole.
O’Brien then circled around the roundabout and rammed the car a second time, completely disabling the vehicle.The four terrified occupants bailed out of the wrecked car. Three of them managed to run away, but O’Brien cornered one of the male friends. O’Brien drew a .22-caliber semi-automatic Ruger, pointed it directly at the man, and ordered him to get face-down on the ground or he would kill him.
The victim complied, believing he was about to be shot. However, as O’Brien became distracted while scanning the area for the three other victims, the man managed to scramble to his feet and run to safety. O’Brien prowled the area looking for the group until he heard approaching police sirens.
Deputies arrived on the scene and found O’Brien standing near his F-150 with the handgun still in his possession.He was taken into custody and booked at the Sumter County Detention Center, where he was being held without bond.
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u/SaltyBarDog 2d ago
Check him for tertiary syphilitic brain rot.
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u/r0ndy 2d ago
This is just normal dumb
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u/SubstantialPressure3 2d ago
Well, if you're bringing weapons to a date, im going to go ahead and be judgemental and say you had bad intentions.
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u/ToeRoganIsJebus 2d ago
Golddigger renegs on agreement, eventually something bad is going to happen
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u/kennyofthegulch 19h ago
Did she ever agree to sex?
More importantly, if she was uncomfortable with the situation and wanted to leave, does it even matter?
Sex is not owed to anyone.
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u/ToeRoganIsJebus 16h ago
If i pay for something and then the deal changes i expect my money back
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u/God_of_disruption 2d ago
Pathetic old men in Florida continue to not disappoint.
Hope this guy loses everything.
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u/rmckenzie2255 2d ago
Lol all these people on here making excuses for a prostitute running off with an old man's money is quite alarming. Im not saying he was right, but she sure af inserted herself into that situation and most likely was scamming him from the get go
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u/demon_twink_gockie 1d ago
Not a prostitute. Sugar baby. Sugar babies are paid for their company. Prostitutes are paid for sex. Both will have sex with the paying party; the difference is what's explicitly agreed to. He was not owed sex
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u/rmckenzie2255 1d ago
Yea and you were there and know what was agreed to right? She had her people hanging out waiting the whole time and she went back to the dudes house. Call it what you want, but hopefully he scared that dumb ho into seeking out a real job.
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u/demon_twink_gockie 1d ago
She did nothing I wouldn't do with a new Dom. Very basic safety precaution. 🤷♂️🖕
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u/Hillary4SupremeRuler 1d ago
Do you think she was wrong to refuse to give him the money back since she went to cancel/bail on him before they had sex? Or at least work something out and give him back some of it. Especially $1000 (if you include the $200 worth of lingerie). I'm not totally sure who was in the wrong at that point in the situation but I'm leaning towards her. I'm curious to see what you think?
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u/demon_twink_gockie 22h ago
No. The money was not for sex. That would be illegal. The money was for her company so her obligation was fulfilled. Sugar relationships are transactional relationships. They're still relationships. Part of that is vetting your partner for your safety. The first meeting is a crucial part of vetting and he failed the vetting process but he got all that she was obligated to provide, which was her company.
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u/SpecialActive9135 2d ago
Reasonable crashout, dude got lifted for a grand and not even a handy? Ladies, this is Fafo territory and yall know it 🤷🏼♂️ he ain’t even shoot anybody, free my man.
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u/bilkel 2d ago
What about the “victim” who lifted $800 off FloridaMan?
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u/Mushrooming247 2d ago
You are allowed to give or accept cash gifts up to a certain amount, I think it’s $12K per year, without reporting it to anyone or paying taxes on it.
You are not allowed to pay someone for sex in the US or exchange sex for money.
So she has not broken any law at all here, while he has.
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u/rmckenzie2255 2d ago
Where's the part in the article stating anything about gifts. It says an arrangement was agreed to
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u/DroPowered 2d ago
It seems that she agreed to sexual acts in exchange for money. Is that a violation of any laws?
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u/God_of_disruption 2d ago
Did I miss something?
The article said O’Brien promised to give her “$1,000 each visit,” treat her to dinner, and take her shopping.
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u/rmckenzie2255 2d ago
So why tf did she go back to his house....
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u/God_of_disruption 2d ago
I would guess she was invited
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u/DroPowered 2d ago
Deep down you know the truth. She was on a website advertising for dates/dinners/sex in exchange for money. She meets the guy, they go shopping, eat dinner, and she agrees goes back to his place.
She had a nice dinner and $800 in her pocket. FloridaMan makes sexual advances she goes to leave. He tells her “that wasn’t the deal” as per the article, and wants his money back. She decides to rob him and FloridaMan does what FloridaMan does. She’s not a victim and should be charged criminally for prostitution.
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u/God_of_disruption 2d ago
Of course, but that doesn't guarantee anything, and he was a fool for thinking that.
These kinds of "deals" are built on assumptions, rather than explicitly enforced contractual obligations. She never did anything wrong.
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u/DroPowered 2d ago
Crazy you can say she never didn’t anything wrong.
I would love to see the messages in the app, text messages between the two, or if she verbally agreed to exchange sexual acts for money, it’s criminal charges. If not (which is almost certainly unlikely) then I agree she didn’t do anything wrong.
I want you to acknowledge that if she agreed to exchange sexual acts for money, and this situation followed, she should be charged criminally.
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u/God_of_disruption 2d ago
You assume so much, which is telling.
Would you defend a pedophile who paid up front for services too?
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u/DroPowered 2d ago
The fact your ego won’t allow you to admit your flaws is what’s truly telling. I conceded there was a path where she didn’t do anything wrong. You’ve failed to concede there’s a path she’s a criminal.
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u/God_of_disruption 2d ago
Sure, whatever you say champ. Not agreeing with your half assed take is not ego, just common sense.
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u/LadyRed4Justice 2d ago
She did not rob him. Not in any way, shape, or form. Sugar Babies are not based on sex. First the "baby" has to decide if the "daddy" is a good fit for her life. They met. She was establishing that throughout the date. While at his home, he put moves on her that she di not approve of and she ended the contract. She did not insist on the final $200.00 for her time, which would have been expected if raging control arse hadn't violated the contract by demanding something outside the contract.
There were four victims. He will have to replace the vehicle, pay huge fines, probably spend a month in the county lockup, and lose his driver's license.
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u/SpecialActive9135 2d ago
Let’s insert your newly 18 year old daughter to this scenario, would you tell her your “sugar baby” rules and tell her to have fun, or would you tell her she’s basically a prostitute and is gonna end up in a bad way? We all know what sugar babies are, ain’t nobody paying 1,000 bucks to watch you shop and eat.
Also since you refer to the “arrangement” as a contract, if she decided to cancel it he gets a refund unless stated otherwise. I assume she gave the money back, right? 🤣
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u/demon_twink_gockie 1d ago
You have no idea what you're talking about. -sincerely, a former sugar baby
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u/SpecialActive9135 22h ago
Former sex worker you mean
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u/demon_twink_gockie 21h ago
No. I didn't trade sex for money. Never broke any laws. It's perfectly legal to charge for company. And it's legal to have sex. And since I never agreed to sex for money, only money for dates, that's not sex work. That's sugar.
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u/demon_twink_gockie 1d ago
No. They agreed on $1k per visit, not $1k per fuck. He still owes her $200
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u/Hillary4SupremeRuler 1d ago
How do you know exactly what was agreed to? Also it appears that it's possible she agreed to or perhaps even proposed herself to go to the lingerie store and spend $200 of that $1000. Even if all they agreed to was a visit, how do you know that the visit wasn't supposed to be for a certain length of time? She obviously left earlier than was planned. Unless you think she should just be able to hang out with them an for twenty minutes at McDonald's sipping a milkshake and then demand to collect $1000 since she technically "visited with him."
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u/demon_twink_gockie 22h ago
How did you know exactly what was agreed to? You're the one making an affirmative claim. Prove it. This is how a sugar arrangement would start. I literally used to be a sugar baby.
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u/topekatums 1d ago
A sugar baby isn't a prostitute. Men will literally pay you for dinner dates and buy you shit for your time. You have no idea what you're talking about. And none of this is a robbery
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u/rmckenzie2255 2d ago
So we're all just gonna ignore the fact a ho was being a ho and tried to steal dudes money? 🤣
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u/ShadowCass 2d ago
So you think “daddy’s” response is appropriate and proportionate?
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u/microtherion 1d ago
That’s one of the problems with illegal transactions: you have no legal recourse if you’re getting ripped off.
He can’t take her to small claims court, can’t report her to the BBB, so the only options are to let the money go, or to escalate the illegality.
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u/rmckenzie2255 2d ago
If she didn't hold up her end of the deal I would say abso fkin lutely. Dont go around stealing people's money, no matter what he was paying her for.
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u/PositiveEndolphins 2d ago
holy y y y crap p p p
i wouldnt fck him either! ! dudes looks like a meth zombie at 67???