Delving Into Prince Harry’s Dating History

Television presenter Natalie Pinkham, then 26, and 19-year-old Prince Harry were rumored to be dating in 2003. Although the romance has not been confirmed by either party, the prospect of a seven-year age gap between Pinkham and the world’s most eligible bachelor was scandalous at the time.

Also in 2003 was a rendezvous between the Prince and Cassie Sumner at London's Chinawhite nightclub. Sumner shared her brief brush with royalty in an interview. Despite revealing intimate details, the encounter was, according to Sumner, a one-time thing. 

On-again-off-again from 2004 to 2011, Harry’s relationship with Chelsy Davy was undoubtedly his longest ever. The two met in Cape Town, South Africa during Harry’s gap year devoted to charity work (and apparently, Davy). Davy allegedly opted to study at Leeds University in an effort to remain closer to her then-lover. Yes, it was serious: notwithstanding their 2009 break up, Davy accompanied Prince Harry to his brother’s wedding to Kate Middleton in 2011. Unfortunately though, with the public attention becoming too much for Davy to endure, the royal welcome failed to seal their relationship for good.

Astrid Harbord, a friend of Kate Middleton, spent a night on the town with Prince Harry in 2009, after which the pair reportedly returned to Clarence House at 3 a.m.

Caroline Flack, another television presenter, met Prince Harry in 2009 following an introduction from a mutual friend (and Harry's former girlfriend), Pinkham. Promptly after their relationship went to the press, Flack’s name was already inextricably linked to the prince. Feeling she was a mere accessory to the Prince within the public eye, Flack called the relationship quits. 

Mollie King, a member of the girl group The Saturdays, met Prince Harry for a drink at a London bar in 2010. Earlier that year, the two met during the Asprey World Class Cup polo match. The short-lived affair culminated to a close with Harry, explaining to the press that the singer "was too open about their relationship."

Norwegian singer Camila Romestran alleges that she was served breakfast in bed by the prince after spending a night with him at Clarence House. Prince Harry has neither confirmed nor denied the claim. 

Florence Brudenell-Bruce was Prince Harry’s first girlfriend after his final split with long-term ex-girlfriend Davy. As the daughter of an Earl, the actress and model certainly had the pedigree to please Harry’s royal family. But alas, the relationship was brief, and as always, kept largely under wraps.

After a two-year-long relationship, Mulberry model and actress Cressida Bonas ranks third among Prince Harry’s most serious romantic partners. The two met thanks to an introduction by Harry’s cousins Princess Eugenie and Princess Beatrice in 2012. A familiar trope among Harry’s ex-girlfriends, the couple split when Bonas could no longer bear the public scrutiny.

Ellie Goulding and Prince Harry were seen together at a polo event in Coworth Park, Berkshire. Although no photos exist to prove it, whispers at the time indicate that the two canoodled under a shared blanket during the game.

We know her from Suits and more recently Harry & Meghan, Markle brought Harry’s dating life to a close. Arranged by a mutual friend, Harry and Meghan met on a blind date in July 2016. Since leaving Buckingham Palace in 2020, the couple has relocated across the pond to Santa Barbara, California, where the couple raises their two children Archie Harrison and Lilibet Diana.