The relationships of Matthew Perry have always been a beloved topic for journalists. Chandler, Matthew’s character in ‘Friends,’ had quite a few girlfriends, and the actor tried not to lag behind him. Alas, despite Perry’s affability, the man never found that one and only, unique life companion. Moreover, Matthew was not married even once! The actor himself admitted that he would like to start a family and have heirs. Unfortunately, fate had other plans for the star.

Matthew Perry’s Relationships: A Wandering Heart

Loud Romances

Matthew Perry’s relationships were never considered a taboo subject. The actor saw nothing objectionable in discussing them. Moreover, in his autobiographical book ‘Friends, Lovers, and the Giant Awkward Thing,’ the man openly shared with the world about most of his high-profile romances without hesitation.

For example, one of Matthew’s first celebrity loves was Jennifer Aniston. It’s worth noting that Perry fell for Aniston even before the filming of ‘Friends’ began! Unfortunately, for Jennifer, Matthew remained just a friend. The actress repeatedly rebuffed his persistent advances. Then, Brad Pitt entered Aniston’s life, and Perry finally understood — there was nothing to catch here.

Star Couple

In 1995, Julia Roberts herself appeared in one of the episodes of ‘Friends.’ The celebrity didn’t hide that she joined the show solely because of the charismatic Chandler. The actor deployed all his charm and eventually became Julia’s official beau. Alas, the relationship between Matthew Perry and Julia Roberts lasted only 3 months.

The initiator of the breakup in their relationship was Matthew himself. However, a few years later, the man confessed that he took this step because he was convinced that Julia was only looking for a short adventure. Perry realized that he was starting to fall in love seriously, so he chose to end the relationship first.

Bachelor Adventures

After Julia, Matthew went all in. The actor’s romantic interests were predominantly fellow actresses from popular TV shows at the time. Jasmine Bleeth from ‘Baywatch,’ the beauty Neve Campbell from ‘Party of Five,’ Maeve Quinlan from ‘The Bold and the Beautiful’… However, none of these beauties lingered long in Matthew’s heart.

The first person with whom Perry genuinely tried to be a caring and devoted life companion was volleyball player Rachel Dunn. His relationship with Rachel lasted for two years. After Rachel, Perry dated actress Lizzy Caplan for six years. Alas, Matthew’s attempts at change invariably ended in failure.

The Home Stretch

The last in the long line of official companions in the actor’s life was a literary manager named Molly Hurwitz. Perry dated Molly for three years and even managed to propose to her. Alas, at that time, Matthew faced once again struggles with addiction, leading to the breakup of the couple. Unlike Lizzy Caplan, Molly retained warm memories of Perry. There are also rumors that in the last days before Matthew Perry’s sudden departure from life, he started dating again. However, even the actor’s close friends do not know who his last lover was.