Being a royal has never stopped the Duke of Sussex from living his life on the wild side.
An while he’s now a changed man, his memoir “Spare” speaks of everything from clubs, booze and drugs to hooking up with a cougar who took his virginity in a field behind a pub – this was just the start of his relationship woes that made tabloid headlines more often than not.
The charming prince has also admitted to having “the biggest crush” on “Friends” actress Courtney Cox and partied with her at her mansion January 2016.
The book also name drops plenty of other celebrities like the Spice Girls and a host of supermodels.
We take a look at some of Prince Harry’s celebrity entanglements before he met Meghan, Duchess of Sussex.
Natalie Pinkham
Back in 2003, the young royal was rumoured to have dated TV presenter Natalie Pinkham. While the two have never publicly confirmed a romantic relationship, they reportedly maintained a friendship years after being linked together.
Cassie Sumner
In 2004, glamour model Cassie Sumner who is three years older, hooked up with Prince Harry at a London nightclub. Sumner herself also opened up on the experience, with Prince Harry reportedly inviting them to his private table inside the club.
She revealed that he nuzzled her earlobes and she ran her fingers through his hair.
Chelsy Davy
Prince Harry's longest relationship to date remains his romance with Chelsy Davy, which lasted on-and-off from 2004 to 2011.
The two first met during Prince Harry's gap year in Cape Town, South Africa and continued to date on and off for years.
Davy even accompanied Harry to the Duke and Duchess of Cambridge's wedding in 2011.
Caroline Flack
The late “X Factor UK” host was linked to Prince Harry in June 2009. Flack shared her story, revealing the two began dating after being set up by a mutual friend.
As soon as the relationship went public, however, they called it quits. Flack is also mentioned in “Spare”.
Ellie Goulding
The pop star and Prince Harry were never officially an item but sparked rumours after getting cosy at the polo in Berkshire during the spring of 2016.
The two have reportedly been good acquaintances for years, after Goulding performed at Prince William and Kate Middleton's wedding in 2011 and then again at Prince Harry's Invictus Games in 2014.
Catherine Ommanney
The former “Real Housewives of Washington DC” star revealed that she had a brief but passionate romance with the prince in 2006.
They met at a dinner party in Australia. Ommanney was reported saying that their fling involved drinking at Art Bar in Chelsea and Eclipse nightclub in South Kensington before the pair kept the night going at one of Prince Harry's friend's places in Chelsea.
