Heath’s first girlfriend was supposedly, yesteryear’s actress and singer Lisa Zane, a woman 18 years older to Ledger. Despite the age gap, their chemistry was quite a thing to talk about in 1998 on the sets of Roar, which was also the place where they met. After the show went off, both travelled to Los Angeles, where Lisa started pursuing her career, as a singer. Ledger and Lisa broke up in 1999, citing reasons unstated to the public.

There was a supposed rumor of Heath dating co-actor Julia Stiles on the sets of 10 Things I hate about you where each of their co-stars admitted to both being serious but nothing was quite reported officially and brushed off till his relationship with someone else surfaced soon. Heath’snext relationship was more sort of an affair that started in 1999 with television actress and model Christina Cauchi since both officially broke-up soon but were reported to have been in an on and off relationship even when both seemed to be in another relationship. After an official end with Christina, Ledger started dating blonde actress Heather Graham, whom he met on the sets of A Knight's Tale and hit off instantly as per sources. The cute couple was in the news for about 9 months before breaking up in June 2001.

Heath then dated actress Naomi Watts after they met on the sets of Ned Kelly. The press was in particular quite vocal about their relationship, given that Naomi was eleven years older to Ledger. Their relationship reported started in August 2002 before ending amicably in mid-2004, thus ending a two year old relationship between the two.

The next time, Heath got into a serious relation, it seemed to be a serious one. Actress Michelle Williams and Heath Andrew Ledger first met on the sets of Oscar-winning director Ang Lee’s Brokeback Mountain where they were cast in roles of a couple. They started dating in May 2004 and even had a child in the form of a daughter who was subsequently named Matilda Rose. Rumors were of a supposed marriage came up soon after but were brushed off as the couple broke-up in 2007, also ending the fears of a divorce!

Heath was then linked with several actresses such as Helena Christensen, Kate Hudson, Mary-Kate Olsen and eventually, with stalwart Lindsay Lohan but the last official relation, he had was with struggling star Gemma Ward and both supposedly started dating in late 2007 when Gemma was just 20. Their relationship ended pre-maturely when Heath died in 2008. Several actors and actresses mourned his death, including his ex-partners.