Georgia Toffolo’s long history of red flag men, from cringe CEO to literal criminal

Georgia Toffolo has been in the public eye for over a decade, and as such, she’s got a few skeletons in her closet and a relationship history that resembles a pop culture most wanted list. Ironically, one of them actually went to jail.

Obviously, Georgia is now happily married to former BrewDog CEO James Watt, with the two of them tying the knot in a low-key ceremony in March. Things seem to be going great for them, just recently showing off their shared bank account. Whether they remain together is yet to be seen, but if you’re collectively worth £425 million, are you really in a rush to go anywhere?

Here’s Georgia Toffolo’s relationship history that will leave you with one question: How can someone so smart make so many bad dating choices?

1. Sam Prince

When she entered the limelight as a cast member on Made in Chelsea, Georgia Toffolo’s first public relationship was with Sam Prince in 2017. They were only together a year before Sam slept with another woman in Georgia’s bed, though it did spark this iconic line from one very angry Miss Toffolo: “You f****d somebody in my bed. Oh my God, that is the most disgusting and disrespectful thing.”

Sam has been a major red flag ever since; his last name might be Prince, but he’s basically a Disney villain and one that seemingly started Georgia’s awful taste in men.

2. James Middleton

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James Middleton, the brother of Kate Middleton, was another stamp in Georgia Toffolo’s relationship history in 2016. Besides being a member of the British upper class and landed gentry, which we know is icky anyway, James might have been Toff’s least concerning boyfriend. Unfortunately, she torpedoed that relationship to go on Celebs Go Dating, according to reports.

Though James and Georgia did get back together for a time after the Channel 4 show, she again called it quits to go on I’m A Celeb the following year.

3. Jack Maynard

After I’m A Celeb, Georgia was briefly linked to her campmate Jack Maynard, with them being spotted out together in London. Obviously, this came after he was kicked from the show over racist and homophobic tweets, so it wasn’t the best look.

4. Honourable mention: George Lineker

In 2018, Georgia was pictured with the son of Gary Linkeker, George, as they partied in London before sharing a taxi home. Speculation ramped up from there, but she put rumours to bed soon after.

“I worry now that before going on a date that I’ve already been pre-judged before they’ve even met me. I’m very fortunate with what I’ve got in the diary at the moment, but there are massive drawbacks. When I walk down the street, people shout from their cars and their vans,” she said at the time.

“So at the moment I’m still single and very happy and not looking for anyone at the moment. But a bit of Sunday night company wouldn’t go amiss, but I’ve got my grandparents down the road, so it’s fine.”

5. Charles Goode

Next up on the rollercoaster that is Georgia Toffolo’s relationship history, Charles Goode! Though neither party confirmed nor denied the relationship in 2018, she was pictured planting a kiss on his cheek. Numerous outlets reported that she was dating him at the time.

Nothing really that red flaggy about Charles.

6. George Cottrell

From 2019 to 2023, Georgia was in an on-again, off-again relationship with George Cottrell, a senior advisor to Nigel Farage and former head of fundraising for UKIP. They reportedly split for the final time when George grew close to Miss Montenegro model Andjela Vukadinovic.

A few years before Georgia and George met in 2019, George was arrested during a trip to the US’ Republican National Convention with best bud Nigel Farage. Two years earlier, he had unknowingly met with undercover federal agents in Las Vegas, where he conspired to launder millions of dollars’ worth of drug money using offshore bank accounts. A plea deal was eventually reached, with prosecutors dropping 20 charges in return for a guilty plea to a single count of wire fraud. He served eight months behind bars.

7. James Watt

What to say about James Watt that hasn’t already been screamed by one of his BrewDog employees? Georgia met James through a mutual friend in 2023, and they are now happily married and thriving by all accounts.

Why James Watt is a glaring red flag shouldn’t need pointing out, but here we go: He refused to pay his staff a livable wage, wanted to start the UK version of Elon Musk’s DOGE, launched a pink IPA for International Women’s Day, and so on. There are also tons of accusations about him being an all-around awful person to work for, from him creating a “culture of fear” to making female staff members feel “uncomfortable” and “powerless”.

Following the BBC Disclosure documentary, James denied the claims and told the publication: “Secondly, and more importantly, I hugely regret anyone feeling in any way uncomfortable around me, as the programme set out. This is absolutely the last thing I want and something I will learn from immediately. I truly apologise to anyone who felt that way. This was never my intention.

“However, I would argue that people feeling uncomfortable around me based on false rumours and misinformation does not represent inappropriate behaviour on my behalf.”

She might be Tory, and she might be out of touch, but Georgia deserves better than her messy relationship history.