Caroline Flack Age Gaps: A Timeline Of Her Relationships

By Juliet Smith

19th September 2019

Caroline Flack Age Gaps: A Timeline Of Her Relationships

From heartbreak to Caroline Flack’s age gap flings, we’re taking a look at a timeline of all her relationships…

Although she’s the host of matchmaking TV Show Love Island, Caroline Flack has had a hard time finding her Mr Right, despite her best efforts.

While the 39-year-old spends the majority of her time making us LOL on-screen, she has had some pretty jealous-worthy-but-not-so-successful relationships off-screen too *cough* Prince Harry *cough*.

Here’s the low down of everyone she’s been linked with, from harmless flirting with Harry Styles to serious romances with Jack Street – sadly none worked out for the Flackster.

However, she’s now gone official with her latest boyfriend hunky tennis player Lewis Burton and things are looking good so far.

Let’s take a look back at her entire relationship history…

2009 – Prince Harry

Yep – before our Prince was shacked up with wifey Meghan Markle, he spent some time romancing our very own Flackster. We’re not jealous…

caroline flack age

Image Source/Daily Express

Opening up about their fling, in her autobiography Storm In A C Cup, Caroline revealed:

“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.”

Princess Flack has a nice ring to it, no?

2011 – Olly Murs

There were loads of rumours doing the rounds that Cazza and Olly were a thing. But although they admitted they have the hots for each other, things never blossomed into a proper relationship.

caroline and olly

Image Source/Daily Mirror

The pair admitted that their first year working together on The Xtra Factor was a ‘little bit flirty’…


“We were both single at the time.”


“I did fancy you when we first started.”


“I used to watch you on I’m A Celebrity… Get Me Out of Here Now!, and thought you seemed like a top person. Someone really lovely, who I could go out for a drink and have a laugh with. It’s almost like when you think of girlfriends – you’re the perfect girlfriend.”


Basically, I’m your perfect girl.”


“I think all guys look at you in that way.”

And things STILL didn’t work out *cries*

2011 – Harry Styles

Oh, the absolute outrage when news emerged of the Love Island Host and Harry Styles’ fling?! Cazza, 31, was hosting The Xtra Factor with Olly when her and Harry (then 17) got together.

harry styles and caroline flack

Image Source/Daily Mirror

The pair – who both worked from Simon Cowell at the time – revealed that they attempted to keep their relationship private, but the news broke out after the was papped leaving her home one morning.

In her autobiography, the TV star said:

“I already knew that he had a crush on me, he’s made it pretty obvious as he’s said it in magazines and said it to friends. I’ve never felt I was much older than Harry. I still feel 18 and I probably act that way half the time.”

“It began to go wrong when he was pictured coming out of my house one morning. And that was that. In the street people started shouting ‘paedophile’ at me in the street and ‘pervert’.”

Poor Flacky.

2014 – Jack Street

Caroline began dating musician Sam Smith’s manager Jack and the pair moved in together after eight months of courting.

caroline flack age

However, rumours quickly emerged that Jack had been flirting with Glee Star Dianna Agron and after he encouraged his Twitter followers to vote for Flacky on Strictly, she replied:

 “@jackb_street easing your guilt??? Fill yourself with GLEE Jack.”

Hilarious? Absolutely. Subtle? Not so much…

2018 – Andrew Brady

After just one month of dating (uh oh), presenter Caroline and The Apprentice star, Andrew, had moved in together. In April, Caroline posted on her Instagram confirming her engagement with Andrew, showing off a picture of herself wearing a diamond ring.

Image Source/Evening Standard

Unfortunately, the couple then broke it off after Andrew admitted he’d met up with the Celebs Go Dating bosses. Tut tut.

2019 – Lewis Burton

Last month (August), Flack confirmed her romance with the hunky former tennis player Lewis Burton with an Instagram selfie captioned:

caroline flack age

Image Source/Instagram

“Best weekend ❤️ @lewisburtonofficial,” alongside a picture of her kissing the model.

According to a source:

“Lewis has been a true gent to Caroline and has patiently waited to see her. She has been jetting back and forth between London and Majorca as she juggles her presenting commitments but they have been spending time together when they can.

“They feel comfortable in each other’s company and it seems to be going in the right direction.”

Things are looking good for our Flack…

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