Prince Harry’s exes – Inside his dating life before Meghan Markle

Serious/Exclusive Dating


The Royal family are notoriously private when it comes to dating, doing their upmost best to keep any romances out of the limelight.

While some members have had their relationships become the focus of public scrutiny, others manage to maintain a private love life.

One who didn’t quite master it was Prince Harry, who found himself at the centre of various rumoured romances over years.

Here we take a look back through the Prince’s dating history, from Ellie Goulding to wife Meghan Markle

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Natalie Pinkham

A young Prince Harry was rumoured to be dating TV presenter Natalie Pinkham in 2003.

The pair never confirmed nor denied having a romantic relationship.

However, Harry and Natalie are said to have remained close pals for many years despite being linked romantically.



Prince Harry was rumoured to be dating Natalie Pinkham back in 2003
Prince Harry was rumoured to be dating Natalie Pinkham back in 2003

Natalie, now 44, is a reporter for Sky Sports F1, and is married to Owain Walbyoff who she shares two children with.

Cassie Sumner

Glamour model Cassie Sumner caught the Prince Harry’s eye when they were both out partying at noughties hotspot Chinawhite nightclub in London.

The interaction happened back in 2004, when Harry was just 21 while Cassie was 19.

She revealed in an interview that he had invited her over to his private table and the pair shared a flirty evening together.



Cassie Sumner spent a night with Harry back in 2004
Cassie Sumner spent a night with Harry back in 2004

Prince Harry’s interest in Cassie seemed to be for one night only however, and the pair weren’t linked romantically again.

Chelsy Davy

Chelsy Davy dated Harry from 2004 until 2011, making it the Prince’s longest relationship to date.

Their romance was on and off throughout the years, after they first met during Harry’s gap year in Cape Town.



Chelsy and Harry enjoyed an on-off relationship with spanned many years
Chelsy and Harry enjoyed an on-off relationship with spanned many years

Chelsy was Harry’s date to William and Kate’s royal wedding in 2011, after rekindling their romance once again. Eventually the pair called it quits once and for all, but still remain close pals.

Chelsy was even one of the many guests who were invited to Harry’s wedding to Meghan.

Astrid Harbord

A close pal of his sister-in-law Kate, Astrid Harbord was rumoured to be enjoying Prince Harry’s company in 2009.

The pair were spotted hanging out in London, prompting speculation they were enjoying a secret romance.



Astrid is good friends with Kate Middleton
Astrid is good friends with Kate Middleton

While Harry and Astrid never confirmed nor denied the rumours, they were pictured multiple times over the years at various different events together.

However, it was said that once things got serious between Harry and Meghan, he cut ties with the socialite Astrid.

Caroline Flack

Prince Harry enjoyed a brief romance with TV star Caroline Flack in 2009.

The pair met through a mutual friend, but once it became public knowledge they quickly called it quits.



Caroline and Harry enjoyed a brief romance
Caroline and Harry enjoyed a brief romance

Caroline previously spoke about her time with Harry, saying: “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.”

Camila Romestrand

After splitting with long-term girlfriend Chelsy Davy, Harry enjoyed a brief romance with Camila Romestrand.

Camila, a Norwegian singer, previously told how she stayed over at Clarence House with the Prince, and how he even served her breakfast in bed.



Camila Romestrand claimed she stayed over at Clarence House
Camila Romestrand claimed she stayed over at Clarence House

Her account of their time together has never been confirmed nor denied, with Harry remaining tight-lipped about his romantic encounters.

Florence Brudenell

Florence Brudenell was first linked to Prince Harry in 2008, but it wasn’t until 2011 that their romance was confirmed.

Harry apparently spent time at the model’s home in Notting Hill, London, where they enjoyed secretive dates together.



Florence Brudenell is a model and actress
Florence Brudenell is a model and actress

Florence reportedly ended their relationship after growing concerned about the Prince’s ‘wandering eye’. She is now married to multi-millionaire Harry St George.

Florence recently spoke out about her time with Harry, saying she felt ‘lucky’ it didn’t work out and described how her ‘privacy ended abruptly’ once the relationship became public knowledge.

Cressida Bonas

Having been introduced by mutual pal Princess Eugenie, Cressida and Harry hit it off instantly.

Harry dated the actress from 2012 until 2014, but it wasn’t meant to be.



Cressida struggled with the media attention that came with dating Harry
Cressida struggled with the media attention that came with dating Harry

Cressida allegedly couldn’t cope with the public scrutiny that came with being in a relationship with a royal, and cut all ties with the Prince.

Mollie King



Singer Mollie was reportedly too open about her relationship with the Prince
Singer Mollie was reportedly too open about her relationship with the Prince

The Saturdays star Mollie revealed she’d enjoyed a brief romance with Prince Harry back in 2012.

Rumours first began circulating after the pair were spotted at a London bar together that year.

However, Harry quickly shut things off after Mollie opened up publicly about their romance.

Ellie Goulding

Singer Ellie Goulding was linked to Harry in 2016, after they were spotted looking cosy at the polo in Bershire.

While they were never officially an item, reports claimed that they seen kissing that evening.



Ellie and Harry are close pals
Ellie and Harry are close pals

The romance was never confirmed, but Ellie and Harry are known to be close pals. She performed at Kate and William’s 2011 wedding, and at Harry’s Invictus Games back in 2014.

Meghan Markle

Prince Harry began dating Meghan Markle in 2016, and unlike his previous flings, their romance become seriously very quickly.

It wasn’t long until the media caught wind of the Prince’s new girlfriend, and he eventually had to release a statement urging the public to quit harassing Meghan.



Harry began dating Meghan in 2016
Harry began dating Meghan in 2016

However, they still managed to maintain a mostly private relationship, enjoying trips and dates together out of the public eye.

After Meghan met the Queen, she and Harry announced they were engaged with a series of gorgeous portrait shots.

The pair then tied the knot in 2018 in a lavish ceremony, and have since welcomed two children together, Archie and Lilbet.

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