Jon Cryer's Second Try At True Love Might Not Have Blossomed Because She Believed He Was Gay

Feb 22, 2023 by apost team

Jon Cryer is an accomplished actor, director, and screenwriter who has been a prominent figure in the entertainment industry for over three decades. Born on April 16, 1965, in New York City, Cryer was raised in a family of actors and performers, which sparked his interest in pursuing a career in acting at a young age.

Jon began his acting career in the 1980s and quickly rose to fame with his breakout role as Duckie in the 1986 film "Pretty in Pink." The film's success catapulted Jon into the spotlight, earning him critical acclaim and a loyal fan base. He continued to work steadily in Hollywood, appearing in films like "Hiding Out" and "Morgan Stewart's Coming Home."

In 2003, Jon landed the role of Alan Harper on the hit CBS sitcom "Two and a Half Men." His portrayal of the neurotic and lovable Alan Harper earned him two Primetime Emmy Awards for Outstanding Supporting Actor in a Comedy Series. Jon's success on the show led to numerous other opportunities, including directing several episodes of the series and writing the screenplay for the 1998 film "Went to Coney Island on a Mission from God... Be Back by Five."

Despite his success, Jon has also faced personal struggles throughout his life. In his memoir, "So That Happened," he revealed his battles with addiction and depression, as well as his difficult experiences with dating and relationships. Jon has been open about his struggles and has used his platform to raise awareness about mental health issues.

Jon's personal life has been marked by both highs and lows. His first marriage ended in divorce, which led to a bitter and long custody battle. Read on to find out how Jon was able to find true love again in his second marriage.

Jon's life has been marked by both success and struggle. From his early breakout role in "Pretty in Pink" to his award-winning portrayal of Harper on "Two and a Half Men," Jon has established himself as a talented actor and filmmaker. However, he has also faced personal challenges.

Jon's first marriage was to British actress Sarah Trigger. The two met while working on the film "Hot Shots!" and were married in 1999. They welcomed a son, Charlie Cryer, in 2000. However, the couple's marriage was fraught with difficulties, and they eventually divorced in 2004. Jon later revealed in his memoir that Trigger had struggled with mental illness and substance abuse during their marriage. After the split, Jon and Trigger went back and forth to court over legal custody of Charlie, while Jon continued to pay tens of thousands to Trigger, who herself was struggling financially, in child support. 

In his memoir, Jon revealed he fell into a slump after his divorce. He said:

"I was in a bad state right after my divorce, and I certainly didn't feel dateable. I was an emotional basket case. What good was I to any woman I might have interest in?" 

However, Jon needn't have worried too much as he would soon meet entertainment reporter Lisa Joyner. The two were married in 2007 and have been together ever since. They adopted a daughter, Daisy, in 2009.

Prior to walking down the aisle, Jon told People 2006: "My son is just the happiest thing in my life. I'm loving being a daddy, and … Lisa and I are really looking forward to watching him grow."

However, it wasn't all smooth sailing for the happy couple. In October 2020, Jon shared a grand chronicle about losing his wedding band in a lengthy Twitter thread.

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Jon said he realized the ring had slipped off his finger as he was walking along the Vancouver coast. "I panicked. I looked around trying to see if something was glinting on the pavement. But it was raining and there were only a few lamp posts with working lights," he wrote. After vigorous attempts to find it, he enlisted the aid of a professional ring finder. With a metal detector, the man was finally able to find the ring. 

Joyner later told People she was ecstatic about the rediscovery. "I was really happy. I was mostly happy for him because I knew he was really sad about it," she stated. "It was meant to be. We're not meant to lose that ring. We've been through too much with each other. I felt so relieved." She also remarked that the ring finder "not only found a ring," but "may have saved a marriage."

She added:

"That ring meant so much. It has so many memories behind it. Now Jon go get it resized!" 

While Jon and Joyner are a picture of wedded bliss now, it might not have worked out for them if Joyner had kept to her first impression of him. Jon and Joyner chatted with CBS Sunday Morning and revealed their rocky start. Jon confirmed it took him six weeks to make the first move, while Joyner had a startling revelation. 

"I thought he was going to be my new best gay friend!" she said with a laugh.

However, she said she knew he was "the one" after their first kiss:

"We got to know each other. And had it not happened that way, I don't think we'd be together. But, when we did kiss… I was done. I really was done. I said, 'Oh, okay!'"

Did you know Jon Cryer's personal life was filled with so many ups and downs? Do you miss watching him on "Two and a Half Men," too? Let us know, and be sure to pass this on to friends and family.