John Mellencamp says he was a 's****y boyfriend' to Meg Ryan: How their decade-long relationship played out

Meg Ryan and John Mellencamp attend Taormina Film Fest 2013 2013 at Teatro Antico on June 20, 2013 in Taormina, Italy. (Photo: Venturelli/Getty Images)
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Meg Ryan and John Mellencamp parted ways several years ago now, but there's still love there — at least on his side.

The "Jack & Diane" singer-songwriter, 71, is reflecting on his nearly decade-long relationship with the 61-year-old When Harry Met Sally... and Sleepless in Seattle star, which ended in a broken engagement in 2019. In a new interview with Esquire, he said, "I love Meg Ryan. I went with her for 10 years. She doesn’t love me so much. She’s a great girl. I’m just a s****y boyfriend."

That's not the first time he's hinted that his relationship skills needed work. Let's take a look back at their roller-coaster romance.

November 2010: Ryan and Mellencamp quietly begin dating.

December 2010: Just before the new year, Mellencamp and third wife model, Elaine Irwin, announce they've amicably separated after nearly two decades. They share two sons; he's a father of five.

January 2011: News breaks Jan. 4 that Mellencamp and Ryan, who was previously married to Dennis Quaid, are dating after they are photographed together in NYC. People magazine reports the romance began seven weeks earlier.

NEW YORK - JANUARY 05:  Actress Meg Ryan (L) and singer John Mellencamp leave E.A.T. restaurant on January 5, 2011 in New York City.  (Photo by Ray Tamarra/Getty Images)
Meg Ryan and John Mellencamp leave E.A.T. restaurant on January 5, 2011 in New York City. (Photo: Ray Tamarra/Getty Images) (Getty Images)

Less than two weeks later, Mellencamp files for divorce from Irwin in his home state, Indiana. He lists their separation date as Sept. 1, 2010.

Mellencamp and Ryan — who's mom to Jack Quaid and Daisy Ryan — are photographed together in New York City (where she lives), in Marthas's Vineyard (where she has a summer home) and Bloomington, Indiana (where he lives). However, they try to keep their romance private.

August 2011: Mellencamp's divorce is final.

June 2013: Mellencamp speaks at a "Meet the Creators" event at a NYC Apple Store in June and Ryan looks on from the audience. They couple makes their public debut at the Taormina Film Fest 2013 in Italy.

NEW YORK, NY - JUNE 24: Meg Ryan and John Mellencamp are seen in Tribeca on June 24, 2013 in New York City. (Photo by Alo Ceballos/FilmMagic)
Meg Ryan and John Mellencamp are seen in Tribeca on June 24, 2013 in New York City. (Photo by Alo Ceballos/FilmMagic) (Alo Ceballos via Getty Images)

December 2013: Mellencamp says living in New York City isn't for him for several reasons, including the paparazzi. "I don't give a f*** about me, but I don't like it for [Ryan]," he tells Rolling Stone. "I'm not leaving Indiana. I'm going to die here."

August 2014: Ryan and Mellencamp split. "Distance" is to blame.

September 2014: "Meg is an angel," Mellencamp says on SiriusXM'S The Howard Stern Show. "We tried to have a relationship for three years long distance." However, he hints it may not really be over, saying, "We'll see what happens."

October 2014: They're photographed together again, but it fizzles soon after.

September 2015: He starts dating Christie Brinkley.

August 2016: He and Brinkley split.

March 2017: Mellencamp tells Stern in a March 1 interview that Ryan "hates me to death." He said: "Oh, women hate me. I loved Meg Ryan. She hates me to death... I think it's because I'm a child. I throw fits, I gripe, I complain. I'm moody. Every bad thing that a fella can be, that's me." He said he tried to make nice with Ryan after their split. "I've done that. She just doesn't want anything to do with me. And I can't blame her."

The day the interview airs, he's photographed with Ryan in NYC.

July 2017: After more sightings of the pair, it's confirmed they're officially back on. "They have a bond," a source tells People. They remain very low-key.

December 2017: There are attempts at family blending. They watch a Knicks game with his son Hud (with Irwin) and her son Jack (with Quaid). Mellencamp is also photographed with Daisy, the daughter Ryan adopted.

<<enter caption here>> at Madison Square Garden on December 25, 2017 in New York City.
Hud Mellencamp, John Mellencamp, Meg Ryan and Jack Quaid at Madison Square Garden on December 25, 2017 in New York City. (Photo: Getty Images) (Getty Images)

June 2018: Rumors swirl the couple secretly married. It turns out to be untrue.

October 2018: She's photographed wearing an engagement ring on Halloween.

November 2018: Ryan confirms their engagement on Instagram, sharing a doodle of herself with Mellencamp that he drew with the caption: "ENGAGED!"

December 2018: On the Today show, Mellencamp says, "I'm engaged at 67 to a very funny woman. Funniest woman I've ever met." Of their past ups and downs, he said, "One can well imagine, I'm probably not the easiest guy to get along with. So let's leave it at that."

April 2019: Mellencamp, also an artist, shows off to Architectural Digest a Soho loft he purchased in January 2018 near Ryan's NYC home. He says it's good for their relationship, explaining, "When I was [at Ryan's home], there was no place for me to paint, no place for me to write, so I bought this little place.”

August 2019: Ryan tells InStyle they aren't rushing down the aisle. "Yes, I'm going to get married at some point," she says. "But for now this engagement thing is a state of grace."

NEW YORK, NY - DECEMBER 03:  John Mellencamp and Meg Ryan seen on the streets of Manhattan on December 3, 2018 in New York City.  (Photo by James Devaney/GC Images)
John Mellencamp and Meg Ryan seen on the streets of Manhattan on December 3, 2018 in New York City. (Photo: James Devaney/GC Images) (GC Images)

October 2019: Ryan is photographed without her ring in L.A. News breaks that Ryan ended the engagement. "She'd had enough and ended [it]," an Us Weekly source says. "She has no regrets."

November 2019: People reports Mellencamp didn't want to get married for a fourth time. Sources also tell the outlet the pair, both very independent, had "a volatile relationship from the beginning. They love each other, but there are disagreements which can become issues... He doesn't mean to be gruff, but it can happen and it's hard to be around. They fight and make up and fight and make up."

Soon after, she's seen wearing her engagement ring again, but the reconciliation is fleeting.

2020 to 2022: He's linked to beauty expert Nurse Jamie (Jamie Sherrill), realtor Natasha Barrett and skin care expert Marianelly Agosto (who he met through daughter/Real Housewives of Beverly Hills's Teddi Mellencamp). Any new romances for her are under the radar.

June 2023: Mellencamp brings up his famous ex in a "What I've Learned" essay for Esquire. First, he gives rare insight into their relationship when the first got together, saying, "Meg Ryan had just come out of her shell; I had just come out of my shell. We started dating. And we decided to do things on our own instead of having people do stuff for us. We were so f***ing lost. We didn’t know how to do anything. I've never checked out of a hotel by myself. Her and I went to a grocery store, and they wanted our credit card, and we looked at each other and said, 'Here it is,' and they said, 'No, you've got to put it in this thing,' and we went, 'Then what happens?' We laughed at how stupid we are, so hard we cried. I think she's learned how to do everything, and I've learned how to do nothing."

He goes on to profess his love for her, but makes it clear he's too frustrating as a partner, adding, "I love Meg Ryan. She doesn't love me so much. She's a great girl. I'm just a s****y boyfriend."

To be continued...