Over the years, the Friends star struggled with a years-long addiction to alcohol and opioids, subsequently hurting many of his romantic relationships.
This time last year, the 17 Again star — who had been spotted on a Malibu lunch date with a mystery brunette just last month — revealed he had been sober for an unspecified amount of time and admitted he was finally looking for a supportive partner to build a life with.
He had never been married but had proposed to literary agent Molly Hurwitz, his last public relationship, in 2020 after two years of dating.
Derailed love life: Matthew Perry had been in and out of rehab, which derailed much of his love life, before he tragically passed away on Saturday. Over the years, the Friends star struggled with an addiction to alcohol and opioids, subsequently hurting many of his romantic relationships and ability to settle down
However, the pair called it quits six months later since he had been in ‘a really dark place’, which affected their connection.
‘You can only held someone so much,’ a close friend of Hurwitz, who was 22 years his junior, told In Touch around the time of their split. ‘He is in a really dark place and pals fear he may have relapsed.
At the height of his career, he had been romantically linked with many glamorous stars in Hollywood.
He had also attributed much of his short-lived romances to being ‘burned’ by women who were only after his money.
He opened up about his past relationships, which were affected by his addiction, in his memoir Friends, Lovers and the Big Terrible Thing — which was released in November 2022.
He explained that due to his addiction, he only had short-term relationships and was unable to settle down with anyone for too long.
In his book, he touched on dating Julia Roberts for about a year from 1995 to 1996 and how he sabotaged their relationship by ‘dumping’ her before she could leave him.
He wrote that he felt like he could ‘never be enough’ for her.
‘Dating Julia Roberts had been too much for me,’ he wrote in his book. ‘I had been constantly certain that she was going to break up with me.’
He had short-lived romances with stars including Scream actress Neve Campbell, Cherry alumna Heather Graham, and Baywatch star Yasmine Bleeth.
His ex-fiancé: Perry’s latest serious relationship was with literary agent Molly Hurwitz. The pair got engaged in November 2020 but called it quits seven months later
First public romance: He dated Julia Roberts for about a year from 1995 to 1996 and how he sabotaged their relationship by ‘dumping’ her before she could leave him
Brief fling: He dated Baywatch star Yasmine Bleeth for a brief period in 1996
Dating his costar: He dated his Three to Tango costar Neve Campbell in 1998. The couple became close while filming but had called it quits before the rom-com even hit theaters
Short-lived romance: From 2002, Perry was linked to The Bold and The Beautiful star Maeve Quinlan. The pair, pictured three years after breaking up, eventually called it quits in 2003
Just months together: He also had a brief fling with Cherry star Heather Graham in 2003
Getting serious: The actor’s most controversial relationship was his two-year love affair with fashion student Rachel Dunn, pictured, who was 14 years younger than him. They dated from 2003 to 2005
Brief romance: He was briefly linked to Gilmore Girls star Lauren Graham in 2008 before they called it quits several months later
His longest love: The actor’s longest relationship was with Lizzy Caplan of Mean Girls fame. They dated from 2006 to 2012
He also had a controversial two-year relationship with fashion student Rachel Dunn, who was 14 years his junior.
His longest relationship was with Mean Girls’ star Lizzy Caplan — which lasted for six years from 2006 to 2012.
After their split, he stayed out of the limelight and was reportedly celibate for nearly half a decade.
On Saturday, TMZ reported that Perry was found unresponsive after an accidental drowning in the jacuzzi of an LA-based home.
No drugs were found at the scene and there was no indication of foul play, the outlet reported.