When Clarence House announced that 33-year-old Prince Harry was engaged to 36-year-old American actress Meghan Markle, there was a collective cry of “it should have been me!” that echoed around the world.

However, for some ex-girlfriends, that phrase rang particularly loudly in their ears because they had come very close to winning the royal gauntlet that thousands of girls, if not millions, were willing to compete in the race for.

The “Playboy Prince”, as he was affectionately dubbed, appeared to have a particular taste for attractive, blonde society girls in his youth. Other than his long-term girlfriend, Chelsy Davy, the young prince was synonymous with quick flings.

The fifth in line to the throne left quite a colorful trail of women in his wake – from actresses to models, he seems to have collected them all. With the Prince now firmly committed to his fianceé, let’s remind ourselves of the ones who got away!

1. Astrid Harbord 

In 2009, Prince Harry was seen on multiple occasions with PR girl Astrid Harbord, who is pictured on the bottom left of this photograph. She was introduced to the young royal by none other than Kate Middleton, the future Duchess of Cambridge.

The red-headed prince was embarrassingly photographed returning to Clarence House in the early hours of the morning with the blonde socialite, who looked a little worse for wear after the two had enjoyed a night of partying together.

A month later, the Playboy Prince was spotted with Harbord once again leaving an illegal rave in East London in a car bound for Clarence House, sparking rumors that the two were dating.

Whatever arrangement the pair had quickly came to an end, with the young royal soon turning his attention to his military career.

2. Natalie Pinkham

But before Harbord came Formula 1 Racing presenter, Natalie Pinkham, who the Prince allegedly dated in 2006.

The pair, who have remained close friends, apparently had a brief fling over ten years ago while Harry was on a break from on-again-off-again girlfriend Chelsy Davy.

Despite the fact that it was only a brief romance, Harry was reported to be “absolutely infatuated” with the brunette reporter.