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John Mellencamp and Meg Ryan split: How couple went from house-hunting together to breaking up yet again

John Mellencamp has been in almost a dozen relationships, but his romances with Meg Ryan received the most media attention by far
UPDATED JUN 16, 2023
John Mellencamp (L) admitted that he was a 's***ty' boyfriend to Meg Ryan and responsible for their split (Larry Busacca, Joe Scarnici/Getty Images)
John Mellencamp (L) admitted that he was a 's***ty' boyfriend to Meg Ryan and responsible for their split (Larry Busacca, Joe Scarnici/Getty Images)

BLOOMINGTON, INDIANA: In a recent life reflection, John Mellencamp, 71, addressed his regrets and failures as Meg Ryan's boyfriend. The singer has acknowledged that during their ten-year relationship, he was a "s***ty" boyfriend to the actress. The 'Hurts So Good' singer, who spoke to Esquire in an interview that was published on June 13, accepted full responsibility for the breakdown of the intermittent relationship, which came to an official end in 2019.

After Mellencamp's divorce from model Elaine Irwin in 2011, he started dating Ryan, 61. The two were in love for three years before calling it quits in 2014. Three years later, they resumed their romance, according to a source who said that "distance" was the reason behind the split. Mellencamp claimed that the 'Sleepless in Seattle' actress and he had both recently emerged from their "shells" when they began dating, as per Independent.


 
 
 
 
 
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A post shared by John Mellencamp (@johnmellencamp)


 

Early days of romance

At the beginning of 2011, there were rumors that the two were dating after they were seen shopping and sipping coffee together in Martha's Vineyard and New York City. A source close to Ryan, however, said that the couple started dating in 2010, just a few months after Mellencamp's divorce from model Elaine Irwin, his wife of 18 years. People who saw them said they appeared happy and at ease. The artist and actor initially kept their newfound love private, but when they were seen holding hands in early 2011, they were compelled to come public.

Meg Ryan attends the Academy Of Motion Picture Arts And Sciences' 11th Annual Governors Awards at The Ray Dolby Ballroom at Hollywood & Highland Center on October 27, 2019 in Hollywood, California.
Meg Ryan attends the 11th Annual Governors Awards in Hollywood, California (Kevin Winter/Getty Images)

'Distance' drove a wedge

Mellencamp and Ryan's initial romance ended in 2014 as a result of their inability to sustain a long-distance relationship. "She lives in New York and he resides in Indiana," a source informed People at the time. "It was the long distance that ultimately was the cause." In 2013, Mellencamp thought about relocating to New York City, but he couldn't stand to leave his home state. Both celebrities moved on quite fast, with Ryan opting to take a break from romances for a year while Mellencamp dated model Christine Brinkley in the meantime.


 
 
 
 
 
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A post shared by John Mellencamp (@johnmellencamp)


 

Engagement in 2018

Mellencamp and Ryan's separation wasn't forever, as they reconciled in 2017. Although it appeared that the two were getting along, Mellencamp revealed more about the actress in a Sirius XM interview with Howard Stern in March 2017. "Oh, women hate me," he muttered. "I loved Meg Ryan. She hates me to death." The pair got engaged a year later. Ryan announced the engagement in a now-deleted Instagram post that featured a hand-drawn picture of herself and Mellencamp with the caption "ENGAGED!" The couple broke up their engagement in 2019, so their happiness was evidently short-lived.

House hunting in New York

According to Daily Mail, Ryan and Mellencamp started looking for a home two months after they announced their engagement. The two were spotted seeing new houses in Upstate New York and Connecticut at the time. The celebrity couple was led outside of the home by what appeared to be a realtor. According to reports, the stunning house the two were viewing had seven bathrooms, five bedrooms, and a heated saltwater pool.

Actress Meg Ryan attends American Film Institute's 45th Life Achievement Award Gala Tribute to Diane Keaton at the Dolby Theatre on June 08, 2017 in Hollywood, California.
Meg Ryan attends American Film Institute's 45th Life Achievement Award Gala Tribute to Diane Keaton in Hollywood, California (Frederick M Brown/Getty Images)

'He didn’t want to get married again'

The couple had officially broken up by 2019. "He didn’t want to get married again," a source told People at the time. Mellencamp had already tied the knot three times. The source stated, "He loves her, but marriage never seemed to be a part of it. It’s unclear how important a marriage was to Meg. But they spent a lot of time together and it’s too bad they split. They really got along so well together."

According to E! News, Ryan became "exhausted" with the relationship, leading to its termination. "There were so many ups and downs and it wasn't healthy," a source claimed. "She just needed to get out and not be in that environment anymore ... She cares about John but it was time for her to move on. She knows she made the right decision and is happy."

Singer/Songwriter John Mellencamp performs at the Farmers for Climate Action: Rally for Resilience in Freedom Plaza on March 07, 2023 in Washington, DC.
John Mellencamp performs at the Farmers for Climate Action: Rally for Resilience in Washington, DC (Paul Morigi/Getty Images for National Sustainable Agriculture Coalition)
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