Before enrolling in university, Prince William was linked to Jecca Craig, whom he met during a gap year trip to Africa. He also reportedly dated

In the late 1990s, Davina Duckworth-Chad caught William's eye. Their connection was strong enough for Davina to join William on a cruise of the Aegean Sea in 1999 alongside the Prince of Wales and the Duchess of Cornwall.

Before enrolling at St. Andrews University, William was rumored to have been involved with Natalie Hicks-Löbbecke, the daughter of Major Martin Hicks-Löbbecke. The pair made headlines in 2000 when Natalie was photographed with William at a charity polo match.

Arabella Musgrave was also a rumored fling for William, and though their romance was brief, Arabella later became involved with one of William's friends, per Harper's Bazaar.

Another name that surfaced in 2000 was Rose Farquhar, considered William's first serious girlfriend after finishing his A-levels at Eton. Rose, a singer-songwriter who appeared on The Voice UK, now works for Belvoir Castle, per Town & Country.

Another notable figure in William's dating history is Isabella Anstruther-Gough-Calthorpe, an aspiring actress and socialite. Their paths crossed during a summer trip to Greece when William and Kate were reportedly on a break.