Royal Romances

Prince Harry’s Break-Up With Florence Brudenell-Bruce: Photos of His Other Girlfriends

See photos of the young royal's women, including alleged new squeeze Jessica Donaldson.

The younger royal brother has quite a way with the ladies. The latest news that he's taken his conquests to California, and to a Kate Middleton dead ringer! Rumors are swirling that Harry was allegedly caught canoodling with Jessica Donaldson, a tattooed cocktail waitress in San Diego. (Donaldson denies the rumors.) From "Flee" to Chelsy Davy, see the women who've been linked to Harry's heart.

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Jessica Donaldson (on left)

Harry broke up with his last girlfriend claiming he wanted more time to focus on his military training. Little did we know how focused he was. The prince, who's posted outside of San Diego while he learns to fly Apache helicopters for a second tour of duty in Afghanistan, was seen enjoying a night out at Andaz Hotel's Ivy nightclub about two weeks ago. That's when cocktail waitress Jessica Donaldson caught his eye, according to The Sun. The paper reports he shared a passionate kiss with the 26-year-old Kate Middleton lookalike. A source even told The Sun that the two have been exchanging flirty texts and phone calls, and that Harry is "bowled over" by the brunette. Donaldson admits to spending time with the prince but denies the kiss and any rumors that the two are dating.

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Florence Brudenell-Bruce

Known as “Flee” to her close friends, Brudenell-Bruce is the daughter of a wine merchant and a French artist, and many reports have noted her impressive pedigree, naming her as a descendant of the seventh Earl of Cardigan, who led the Charge of the Light Brigade. But since that Earl was childless, she’s really the descendant of a cousin of his. That would make her an eighth cousin of Harry. She has a degree in the art history from Bristol University, and perhaps she’s putting her aesthetic knowledge to good use now that she’s a lingerie model, appearing in campaigns for Ann Summers and John Lewis. The 25-year-old dated Formula One champion Jenson Button in 2008, and got serious with Harry this June. But after two months, Harry called it quits, leaving us to wonder who’ll be the next royal bride.

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Chelsy Davy

The love of Harry’s life so far is Davy, who was the prince’s on-and-off girlfriend for at least five years, from 2004 to 2009. Her father, Charles Davy, made his fortune by allowing people to pay thousands of dollars to shoot endangered animals in Robert Mugabe’s Zimbabwe, which is not good for royal public relations. She’s known as a wild party girl, and the British press has charted the couple’s turbulent relationship over the years. They’ve reportedly broken up three times before the final one in 2009. When she attended the royal wedding of Prince William and Kate Middleton, however, there was talk that the stormy pair had reconciled again. If that was true, then Davy reportedly dumped Harry one last time because she couldn’t stand another long English winter, opting to return to South Africa instead.

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Natalie Pinkham

You might remember a legendary cover of The Sun in 2006 that read “Dirty Harry,” showing the then-21-year-old prince grabbing the breast of a woman and kissing her cheek. That lady is Natalie Pinkham, and those three-year-old photos were, according to Pinkham, stolen. She threatened to sue, and the tabloid then apologized. Pinkham has repeatedly denied any romantic connection, but the image on that Sun cover has stuck. She’s now a television presenter and a correspondent for BBC Radio 5’s Formula One coverage. She was also the host of Police Interceptors and a star on ITV1’s Dancing on Ice. Pinkham was introduced to Harry by her ex, former England rugby team captain Matt Dawson. She’s since moved on, and is now engaged to longtime boyfriend Owain Walbyoff, a TV executive.

Kris Connor / Getty Images

Catherine Ommanney

Amid rumors of an affair, The Real Housewives of D.C. star Ommanney told the Daily Mail in 2006 that she and Prince Harry shared a “long and lovely kiss”—nothing more—when she was already a mother of two, between marriages and still living in England. Ommanney said she found the prince to be extremely mature despite their 13-year age gap: “He's also got a cheeky sense of humor,” she said. “From the minute we started talking he was making me cry with laughter. He's so funny.”

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Camilla Romestrand

The Norwegian rock star and Prince Harry were apparently linked for a short time in October 2010. Romestrand, the lead singer of a U.K.-based band called Eddie the Gun, allegedly referred to Prince Harry as a gentleman after he served her breakfast in bed.

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Cassie Sumner

Prince Harry reportedly snuggled up to model Cassie Sumner at a club in February 2004, just moments after flame Lauren Pope left the scene. Sumner, 21 at the time, told The People that Prince Harry was undressing her with his eyes: “I knew other people were looking at us, but Harry seemed too drunk to care,” she said. “When I asked him about Lauren he just shrugged his shoulders with a naughty smile.” Sumner also claimed that Harry had kissed her earlobes, ran his hand up her thighs, and ordered Sex on the Beach cocktails for the two of them. The Sun also reported that Sumner was pictured on the website of an escort agency called Max’s Angels.

Ian Gavan / Getty Images

Caroline Flack

The X Factor presenter reportedly called Prince Harry “Jam” while they dated. The pet name, referring to Prince Harry’s strawberry-colored locks, was meant to keep their relationship out of the spotlight. According to The Sun, the two dated in June 2009, during which Flack updated her Facebook status to say, "Caroline loves jam... x.”

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Astrid Harbord

Harbord is a familiar name in royal social circles. A close friend of Kate Middleton, Harbord was seen clubbing with Prince Harry after his breakup with Chelsy Davy in March 2009. The two rendezvoused until the wee hours, but close friends said at the time that the relationship was a mere distraction until Harry patched things up with Davy: “It's definitely not over between them—they are taking things slowly to see if they can fix them." Harbord’s appearance apparently didn’t help fix anything.

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Lauren Pope

The star of the reality show The Only Way Is Essex, which has been described as a British version of The Hills, claims she rejected the prince’s invitation to drinks. The two met one drunken night at a club, and after a long chat and a few laps around the dance floor, the two reportedly exchanged numbers. “I was on a sun bed in my lounge when he called,” Pope told News of the World earlier this year. “He asked if I wanted to meet him with a group of his friends at a bar. He was going soon and I don't think I had time to get ready and I didn't want to meet Prince Harry looking like crap. I panicked and decided not to take him up on his offer.”