Caroline Flack relationship history: Ex-Love Island presenter's former boyfriends

30 January 2020, 17:30 | Updated: 17 February 2020, 21:54

The presenter has some very famous exes
The presenter has some very famous exes. Picture: PA

Caroline's former flames vary from One Direction superstar Harry Styles to Apprentice contestant Andrew Brady.

Caroline Flack's relationship history has been anything but smooth sailing, with the former Love Island presenter frequently making headlines.

The star, 40, has been linked to a number of other men in the public eye and is currently dating 27-year-old Lewis Burton, despite her being charged with assaulting him on December 13th, 2019.

Here is Caroline's relationship history and what exactly went down with her exes.

Prince Harry pictured in 2009, around the time he was linked to Caroline Flack
Prince Harry pictured in 2009, around the time he was linked to Caroline Flack. Picture: PA

Prince Harry

Prince Harry and Caroline's apparent flightier dates back to 2009, after she was introduced to the royal through their mutual friend, Natalie Pinkham.

Speaking about their encounters in her 2015 book, Storm In A C Cup, Caroline revealed: "I knew [Natalie] was friends with Prince Harry, and I’d never met him, so I thought, “Oh that’s quite exciting”, and for a moment I perked up.

"So I was just sitting there and he arrived with a few others in tow and we all spent the evening chatting and laughing.

"To meet a prince is so unlikely it would be weird not to acknowledge it.

"However, once the story got out, that was it. We had to stop seeing each other. I was no longer Caroline Flack, TV presenter, I was Caroline Flack, Prince Harry’s bit of rough."

Harry Styles

Two years later, back when Harry Styles was just 17, Caroline was introduced to the then-member of One Direction as she was the presenter of the Xtra Factor.

Caroline was 31 at the time, and their fling was heavily criticised.

In her book, Caroline wrote: "‘I already knew that he had a crush on me, he’d made it pretty obvious.

"He’d said it in magazines and he’d said it to friends. It was flattering and I found it amusing.

"He was a kind of cheeky man/boy with a captivating smile who got what he wanted."

Harry in 2011, around the time he and Caroline dated
Harry in 2011, around the time he and Caroline dated. Picture: PA

She added: "I’ve never felt I was much older than Harry anyway.

"I still feel 18 and probably act that way half the time — all those years in kids’ telly probably didn’t help.

"Although it was just a bit of fun we decided it was best to keep it to ourselves, as we were both working for Simon (Cowell).

"We were both single, we got on well and we had a laugh."

Harry and Caroline split in early 2012 after, as Caroline wrote: "It began to go wrong when he was pictured coming out of my house one morning.

"And once that was out, it was open season. After that anyone could say anything.

"In the street people started shouting at me “paedophile” and “pervert”."

Jack Street

Between 2013 and 2014, Caroline dated singer Sam Smith's manager, Jack Street.

They were together for around 18 months but split after rumours emerged he'd cheated on Flack with Glee actress, Diana Agron, who appeared in a music video of Sam Smith's in 2014.

However, they reconciled in 2015 after Jack (who is eight years younger than Caroline), was spotted with her at Glastonbury festival.

However, later in the year she slammed Jack for ruining the "best day of her life" as he was pictured with another woman on the day she started her job on The X Factor.

Olly Murs

Back during those Xtra Factor days, Olly and Caroline's chemistry as a presenting duo was undeniable, but they were never in a relationship, despite endless flirting.

Olly was linked to Caroline in 2015
Olly was linked to Caroline in 2015. Picture: PA

They've spoken out about fancying each other in the past, with Caroline saying to Heat World - "I did fancy you when we first started".

Olly then replied: "It's almost when you think of girlfriends - you're the perfect girlfriend".

Andrew Brady

Andrew, 29 dated Caroline from the start of 2018 until close to the end of that year.

The pair shared a turbulent relationship which saw them get engaged and split several times before finally calling it quits in November 2018.

Following his ex-fiance’s arrest, Andrew tweeted: "Sad that I’m not more surprised by the news." Which raised a lot of eyebrows.

Caroline and Andrew were engaged
Caroline and Andrew were engaged. Picture: Instagram

He has also since posted photos of an NDA preventing him from talking about a particular relationship.

While personal details in the document have been redacted, Andrew captioned the post with the hashtag #abusehasnogender.

In an Instagram story post, the former CBB star wrote: ‘It’s exactly a year tomorrow (29/11/18) since I left a very toxic relationship and got away.

"Leaving probably saved my life."

Danny Cipriani

A few months after ending her engagement to Andrew, rumours began circulating that Caroline was seeing sportsman Danny, 32.

The presenter had a short fling with the rugby player, starting around March 2019 and ending by May of the same year.

Just before Love Island 2019 kicked off it was revealed they'd called it quits.

Rugby ace Danny dated the star for a few weeks
Rugby ace Danny dated the star for a few weeks. Picture: Instagram

A source told The Sun: “Caroline and Danny had a lot of fun together and she’s very fond of him – but long-term it wasn’t going to work.

“They’ve decided to end it and stay friends.

“Caroline has a busy summer ahead of her and is already moving on by dating other people."

Bradley Simmonds

Bradley, who is a well-known personal trainer was enlisted by Caroline to help whip her into amazing shape for Love Island 2019 - and that he did.

The pair spent a lot of time together both in and out of the gym, and she even took the 24-year-old to a load of events with her.

She denied any dating, despite them looking cosy, saying: "I wouldn’t want to ruin it because he’s the best thing. He’s the only constant in my life right now."

Ripped PT Bradley was linked to Caroline romantically
Ripped PT Bradley was linked to Caroline romantically. Picture: Instagram

Lewis Burton

Caroline and Lewis went official with their romance in August 2019, posting loved-up selfies together on Instagram.

Since then, the couple have shared a number of romantic snaps from their relationship on social media, most recently from a visit to Winter Wonderland together.

There was some speculation Caroline and Lewis were engaged earlier this year after the Love Island host was spotted with a ring on her engagement finger, but the TV star soon denied the rumours.

was arrested and charged on Friday 13th December for assault by beating.

The bust-up with her boyfriend, Lewis, happened on Thursday 12th December in the early hours of the morning.

In a statement, the Met Police said: “Caroline Flack, 40, of Islington was charged on Friday, 13 December with assault by beating. She will appear on bail at Highbury Corner Magistrates’ Court on Monday, 23 December.

"This follows an incident at approximately 05:25hrs on Thursday, 12 December after reports of a man being assaulted. He was not seriously injured."

After appearing in court before Christmas, Caroline is set to return on March 3rd, and hasn't been allowed to see Lewis in that time.