From the moment Prince Harry stepped into the public eye as a young royal, his personal life has been a constant source of fascination. Over the past two decades, his relationships — both rumored and confirmed — have made headlines around the world. While not every link has been officially acknowledged, each has played a part in shaping the Duke of Sussex’s path toward the man he is today.
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2001 – Natalie Pinkham (Rumored)
Before Harry turned 18, he was linked to British TV presenter Natalie Pinkham. Although both parties denied a romantic connection, the pair were photographed together on multiple occasions, sparking early tabloid frenzy.
2003–2004 – Chelsy Davy (Early Days)
Harry met Chelsy Davy, a Zimbabwean-born law student, in Cape Town. The two began a long on-and-off relationship that would span much of his twenties.
2004 – Cassie Sumner (Brief Encounter)
British glamour model Cassie Sumner was briefly linked to Harry after they reportedly met at a nightclub in London. The connection didn’t last beyond a night of dancing.
2004–2005 – Natalie Pinkham (Renewed Rumors)
The rumors of Harry’s closeness with Pinkham resurfaced in this period, but again, both insisted they were just friends.
2004–2011 – Chelsy Davy (Main Relationship)
Chelsy was Harry’s most significant relationship before Meghan Markle. They endured years of long-distance dating, his military service, and relentless media attention. Chelsy ultimately decided royal life wasn’t for her, ending things for good in 2011 — though they remained friendly.
2009 – Caroline Flack
Harry briefly dated TV presenter Caroline Flack, whom he met through mutual friends. Flack later revealed that once the press found out, the relationship became impossible to maintain.
2010 – Florence Brudenell-Bruce
The Prince was spotted with lingerie model and actress Florence Brudenell-Bruce, but the romance fizzled quickly as Harry focused on military training.
2011 – Mollie King
The Saturdays singer admitted to going on a couple of dates with Harry, but the royal reportedly found her love of media attention too much to handle.
2011–2012 – Cressida Bonas (Early Meetings)
Introduced by Princess Eugenie, Cressida — an actress and model — was first linked to Harry in 2011. They began seriously dating in 2012.
2012–2014 – Cressida Bonas (Official Relationship)
Their romance lasted two years, but Cressida ultimately decided she didn’t want the scrutiny of royal life.
2014 – Camilla Thurlow
The former Miss Gibraltar was linked to Harry after they were seen together on holiday in St. Tropez, though it never became serious.
2014 – Jenna Coleman (Rumored)
The Doctor Who star was seen chatting intimately with Harry at a polo event, fueling dating rumors — but nothing was confirmed.
2015 – Emma Watson (Rumor Mill)
In one of the more surprising stories, tabloids suggested Harry had pursued Emma Watson. The actress quickly shut down the gossip, calling it untrue.
2015 – Princess Maria-Olympia of Greece (Rumored)
Another short-lived rumor connected Harry to the glamorous Greek royal, though there was no evidence beyond social whispers.
2016 – Meghan Markle (The Beginning)
Harry met American actress Meghan Markle through a mutual friend in July 2016. Their romance was confirmed in November that year after intense media speculation.
2017 – Engagement to Meghan Markle
Harry proposed to Meghan with a custom engagement ring featuring diamonds from Princess Diana’s collection. The couple’s love story captivated the world.
2018 – Marriage to Meghan Markle
On May 19, 2018, they married at St George’s Chapel, Windsor Castle, in a globally televised ceremony.
2019 – Parenthood
Harry and Meghan welcomed their first child, Archie Harrison Mountbatten-Windsor, in May 2019.
2021 – Family of Four
Their daughter, Lilibet Diana, was born in June 2021, solidifying the couple’s new life in California after stepping back from royal duties.
Present Day – Meghan Markle
As of now, Meghan remains Harry’s wife and partner in their shared philanthropic ventures, despite ongoing public and family tensions.
Over 23 years, Harry’s dating life has transformed from fleeting nightclub encounters to a global love story — one that continues to make headlines for all the right and wrong reasons.