Matthew Perry Got Burned by Women Who Wanted His Money & He Felt He Was 'Not Enough' – Inside His Love Life

• Matthew Perry found it hard to stay committed in a relationship for years due to his fears.
• Years later, Perry felt confident that he was ready to be a husband and have kids.
• He was always of the opinion that women wanted him for his money.

Matthew Perry died on October 28, 2023. Perry never married and had no kids. However, he had been in a relationship with some Hollywood stars. Some of the people the actor was romantically connected with are Julia Roberts and Cameron Diaz.

Perry struggled with alcoholism for a long time. He said in his memoir "Friends, Lovers, and the Terrible Big Thing" that he lost some of his relationships due to his addiction. However, some of his girlfriends, such as Gabrielle Bober, took him to rehab.

In his memoir, Perry explores some of his relationships. He said he made out with Valerie Bertinelli while her husband, the late Eddie Van Halen, was passed out. Perry also dated Tricia Fisher twice, but their relationship didn't materialize into anything due to his fears.

The "Friends" actor had another make-out session in a closet with Gwyneth Paltrow. Paltrow was just one of the women Perry had a fling with. Perry's first high-profile romance was with Julia Roberts, whom he met while shooting an episode of "Friends." Roberts had agreed to appear in the Super Bowl edition of the sitcom if her storyline was linked with Perry's.

This request started a courtship via fax between Perry and Roberts before they met or spoke on the phone. The two eventually connected in person and dated for a few months. However, to Roberts' surprise, Perry called off the relationship.

By this time, the actor had met Roberts' family in her estate in Tao, New Mexico, in 1996. He explained in his memoir that dating the actress was too much for him. Perry felt he was broken, bent, and unlovable, so he was constantly sure Roberts would break up with him. He wrote:

"Why would she not? I was not enough; I could never be enough (…). So instead of facing the inevitable agony of losing her, I broke up with the beautiful and brilliant Julia Roberts."

After Roberts, he dated Gabrielle Allan. It was during his relationship with Allan that Perry realized alcohol controlled him. The actor would sabotage this relationship and others due to his drug habit and alcoholism. The actor then dated Jamie Tarses, who was there for him during his substance abuse struggles. The two parted ways as Perry needed to process being sober.

Perry also dated Rachel Dunn for two years, but again, this relationship ended in 2005 due to his commitment to staying sober. The actor dated Natasha Wagner, and after their break up, they remained friends. Perry moved on with Cameron Diaz, whom he dated shortly after her break up with Justin Timberlake.

Perry said he looked forward to the future and the idea of getting married and having kids.

Perry's longest relationship was with Lizzy Caplan. The two started their romance as friends with benefits and then dated for six years, during which they almost got engaged but broke up in 2012. The actor's breakup with Caplan hurt him. He often thought that if he had asked her to marry him, they'd have two kids and a house, but instead, he was a grown man living alone at over 50.

The movie star eventually got engaged in November 2020 after asking Molly Hurwitz, whom he started dating in 2018, to marry him. Unfortunately, their relationship didn't work out, and the two parted ways for good in June 2021.

Perry died alone. Still, before his death, he had confessed that he was over his fears of loving that had him breaking up with wonderful women over the years. The actor, who had alluded to being a "rich loner" in an interview, also spoke about the feelings he once had for his co-star Jennifer Aniston.

Perry's Dreams and Feelings for Aniston

Perry wrote some emotional messages to his co-stars on "Friends" in the last pages of his memoir. He thanked Aniston for letting him look at her face for an extra two seconds daily. The actor and Aniston had met years before they appeared on the sitcom, and Perry asked her out. Sadly, she said no and asked if they could be friends, to which Perry also blurted no.

Perry found being on set with Aniston challenging due to his crush on her. He always wondered how long he could look at her so he wouldn't make their time on set weird. This thought led Perry to thank Aniston in his memoir for letting him look at her for those extra seconds.

The actor also revealed that Aniston was the one among his "Friends" co-stars who reached out the most when they all learned he was struggling with alcoholism and drug addiction. After Perry felt confident with his sobriety years later, he was assured he could be in a relationship without fears, self-doubt, and self-sabotage creeping in.

Perry said he looked forward to the future and the idea of getting married and having kids. He added that he grew up around kids and was sure he would be a great dad. The actor also noted that his life was now different as he was no longer being managed by fear as he was in the past:

"I'm feeling more confident, and I'm not afraid of love anymore, so the next girl I go out with, better watch out."

However, Perry's deal breaker in a partner is the suspicion that the other person is primarily interested in the relationship for financial gain. The actor admitted that these scenarios happen more often than people think. So, a vital component of a partner he wanted was someone who had their own wealth.

Sadly, Perry died before he could realize his dreams of having a family of his own. However, he had come a long way in his life, having achieved his sobriety goal, let go of his fear, and become self-confident. Perry will be remembered as an incredible actor and a person who dedicated his life to fighting alcoholism and drug abuse.