Pinkham, a TV sports presented who reports on F1 racing, reportedly first met Prince Harry at the 1999 Rugby World Cup. They briefly dated in 2003, according to Us Weekly. And while Pinkham is now married with two children, she and the prince have apparently maintained a friendship over the years. Here she is pictured interviewing him at the BGC Partners’ Charity Day in London in 2001.

Photo: Getty

Sumner, who previously dated actor Russell Brand, met the prince at London’s Chinawhite nightclub in 2003 and shared a risqué account of the night with a newspaper that begins, “He made eye contact as I stood at the bar with friends and invited me to join his private table. It wasn’t long before he began cuddling up to me.” Apparently it was just a one-time thing. “I can’t see myself getting invited home for tea with Prince Charles and Camilla,” she said.

Photo: Getty

Related article: Body Language Experts Analyse Prince Harry And Meghan Markle’s First Interview

Harbord, a friend of Kate Middleton’s, was briefly linked to Harry in 2009 during the “off-again” phase of his relationship with Davy. According to News of the World, the couple spent a night at a club before heading back to Clarence House at 3 a.m.

Photo: Getty

Harry and Flack, an English television presenter who previously hosted the X Factor, were reportedly introduced by their mutual friend Natalie Pinkham in 2009. Flack is said to have given the prince the nickname “Jam” (“because he’s got jam-coloured hair and he’s really sweet,” she reportedly told friends). But the pressure of the constant attention was too much for the TV host, she wrote in her autobiography Storm in a C Cup: “Once the story got out, that was it,” she said. “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.”

Photo: Getty

Related article: How Meghan and Harry’s Engagement Interview Compares to William and Kate’s

The English singer, songwriter, and model reportedly met the prince at the Asprey World Class Cup at Surrey’s Hurtwood Polo Club in 2010, and she told Closer magazine, “Yes, I have met Harry, and we did go out for a drink.” Harry reportedly broke up with King “because she was too open about their relationship.”

Photo: Getty

The Norwegian rock star reportedly told friends that not only did she spend the night at Clarence House in 2010, Prince Harry served her breakfast in bed in the morning. Harry hasn’t confirmed the account, and the relationship doesn’t seem to have lasted much beyond that.

Photo: Getty

Brudenell-Bruce and Harry reportedly dated in 2011, following his split from Davy. A daughter of the Earl of Cardigan and cousin of English singer Bo Bruce, the blonde model may have been the one to end the brief relationship with the prince. “She felt he had a wandering eye all the time and she wasn’t really into not knowing who he was flirting with or talking to when they were apart,” a source told the Daily Mail. She’s now married to a different ex-boyfriend: multimillionaire banker Henry St George.

Photo: Getty

One of the prince’s serious partners, Bonas and Harry reportedly dated from 2012 through 2014 after being introduced by his cousins Princess Eugenie and Princess Beatrice. Bonas is an actress (she appeared in this year’s Tulip Fever) and sometime model who has worked with Burberry and Mulberry. Despite reports that she and Harry parted amicably, when news broke of the Prince’s engagement to Markle, Bonas posted a cryptic message to Instagramthat read, “No matter how educated, talented, rich or cool you believe you are, how you treat people ultimately tells it all,” with the caption, “Truth #quotestoliveby.”

Photo: Getty

Related article: Watch Prince Harry And Meghan Markle’s First Official Interview As A Couple!

Pop star Goulding and the prince may just be friends, but they certainly have a history together. Goulding sang at Prince William and Kate Middleton’s wedding reception at Buckingham Palace in 2011and at the Invictus Games in 2014. In 2015 Goulding and Prince Harry were reportedly spotted “canoodling” under a blanket at a polo match, and she made a mischievous grin and looked away when she was asked about the Prince on camera. Harry met Markle after a mutual friend set them up on a blind date in early July, 2016, and the rest is history.

Photo: Getty

This article originally appeared on Town & Country US.