John Mellencamp Admits Mistakes with Meg Ryan but Still Holds Love for Her

"I hold a deep affection for my former fiancée, Meg Ryan, but I worry that the feeling may not be mutual," expressed John Mellencamp in a recent interview with Esquire. The musician, who was with Ryan for a decade, referred to himself as a "s—y boyfriend" and praised Ryan as a "great girl."

Mellencamp and Ryan have had a tumultuous relationship since they were first linked in 2011. After breaking up in 2014, they reconciled briefly before calling it quits again in 2015. However, the couple gave their relationship another chance in 2017 and got engaged the following year. Ryan made the engagement official in November 2018, sharing a photo of her new diamond ring on Instagram with the caption "ENGAGED!" Ryan has a son named Jack Quaid, 31, from her previous marriage to Dennis Quaid.

During a one-on-one interview with Today, the singer of "Jack and Diane" expressed his gratitude for being able to marry the Sleepless in Seattle star. At 67 years old, the father of five, including Real Housewives of Beverly Hills alum Teddi Mellencamp, shared that he was engaged to the funniest woman he had ever met. Despite acknowledging that he may not be the easiest person to get along with, he couldn't contain his excitement and appreciation for his soon-to-be wife.

Ryan shared with InStyle in August 2019 that she and John were taking their time with wedding planning and enjoying their engagement for the time being. She explained that being engaged was a "state of grace" for her. In a later interview with the New York Times, Ryan revealed that she and John are able to have fun and enjoy their relationship freely. She even expressed her belief that relationships can be a challenge for everyone, jokingly questioning "who can do it?"

The couple finally ended their relationship that same year, with a source revealing to We that Ryan had decided to break off the engagement as he had reached his limit. The insider also disclosed that Ryan's former partner had no qualms about the split. Nonetheless, John recently shared with Esquire that despite the tumultuous nature of their relationship, they had a lot of fun together, particularly during the early stages of their romance.

After coming out of their respective shells, Meg Ryan and John Mellencamp began dating and made a conscious decision to handle things on their own, without relying on others. However, they quickly realized how lost they were, and often laughed at their own incompetence. According to John, Meg has since learned how to do everything, while he still feels like he knows nothing. Before his relationship with Meg, John had been married three times, with his most recent marriage to Elaine Irwin ending in 2010 after almost 20 years together.

After her highly publicized divorce from Dennis Quaid in 2001 due to her affair with Russell Crowe, Ryan opened up in a 2003 interview with InStyle about the challenges of living under the scrutiny of the media. She clarified that her failed marriage was not solely the fault of her relationship with A Beautiful Mind actor, Russell Crowe, and also revealed that Quaid had been unfaithful during their time together.

“Dennis was not faithful to me for a long time, and that was very painful,” she told the outlet. “I found out more about that once I was divorced.”