How their decade-long relationship unfolded

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)

John Mellencamp talks about his ex-fiancée Meg Ryan in a new interview. (Photo: Venturelli/Getty Images)

Meg Ryan and John Mellencamp split several years ago now, but there’s still love out there, at least on his side.

‘Jack & Diane’ singer-songwriter, 71, reflects on his nearly decade-long relationship with the 61-year-old When Harry meets Sally… And Insomnia in Seattle star, who ended in a broken engagement in 2019. In a new interview with Squire, he said, I love Meg Ryan. I went with her for 10 years. She doesn’t like me that much. She’s a wonderful girl. I’m just a ****y boyfriend.”

This isn’t the first time he’s hinted that his people skills needed work. Let’s take a look back at their roller coaster romance.

November 2010: Ryan and Mellencamp quietly start dating.

December 2010: Just before the new year, Mellencamp and his model third wife, Elaine Irwin, announce that they have amicably parted ways after nearly two decades. They share two sons; he is the father of five children.

January 2011: News drops on January 4 that Mellencamp and Ryan, who was previously married to Dennis Quaid, are dating after being photographed together in New York. People the magazine reports that the romance began seven weeks earlier.

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

Meg Ryan and John Mellencamp leave the EAT restaurant on January 5, 2011 in New York City. (Photo: Ray Tamarra/Getty Images)

Less than two weeks later, Mellencamp filed for divorce from Irwin in his home state of Indiana. It lists their split date as September 1, 2010.

Mellencamp and Ryan – who is the mother of Jack Quaid and Daisy Ryan – are pictured together in New York (where she lives), 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 an Apple Store in New York in June and Ryan watches from the audience. The couple made their public debut at the 2013 Taormina Film Fest in Italy.

NEW YORK, NY - JUNE 24: Meg Ryan and John Mellencamp are seen at 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)

December 2013: Mellencamp says living in New York isn’t for him for a number of reasons, including the paparazzi. “I don’t care about myself, but I don’t like it for [Ryan],” he says rolling stone. “I’m not leaving Indiana. I’m going to die here.”

August 2014: Ryan and Mellencamp have parted ways. “The distance” is to blame.

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

October 2014: They are pictured together again, but it falls apart soon after.

September 2015: He starts dating Christie Brinkley.

August 2016: He and Brinkley separated.

March 2017: Mellencamp told Stern in a March 1 interview that Ryan “hats 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 kid. I throw tantrums, I complain, I complain. I’m in a bad mood. Every bad thing a guy can be is me.” He said he tried to be nice to Ryan after they split. “I did. She just doesn’t want anything to do with me. And I can’t blame her.”

On the day the interview airs, he is pictured with Ryan in New York.

July 2017: After more sightings of the pair, it’s confirmed that they’re officially back. “They have a connection,” says a source People. They remain very discreet.

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

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

June 2018: Rumors are circulating about the couple married in secret. This turns out to be wrong.

October 2018: She is pictured wearing an engagement ring on Halloween.

November 2018: Ryan confirms their engagement on Instagram, sharing a doodle of herself and 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. The funniest woman I’ve ever met.” Of their past ups and downs, he said, “You can well imagine that I’m probably not the easiest guy to get along with. So let’s just leave it at that.”

April 2019: Mellencamp, also an artist, shows off at Architectural Summary a Soho loft he bought in January 2018 near Ryan’s New York 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 In the style they don’t rush down the aisle. “Yes, I will get married at some point,” she said. “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)

October 2019: Ryan is pictured without his ring in LA News breaks that Ryan ended the engagement. “She’s had enough and is done [it],” A We Weekly says the source. “She has no regrets.”

November 2019: People reports that Mellencamp did not want to marry a fourth time. Sources also told the outlet that the couple, who are both very independent, had “a volatile relationship from the start. They love each other, but there are disagreements that can turn into issues… He doesn’t want to be gruff, but it can happen and it’s hard to be there. They fight and make up and fight and make up.

Shortly after, she wears her engagement ring again, but the reconciliation is fleeting.

2020 to 2022: He is related to expert beauty nurse Jamie (Jamie Sherrill), real estate agent Natasha Barrett and skincare expert Marianelly Agosto (whom he met through his daughter/The Real Housewives of Beverly Hillsby Teddi Mellencamp). Any new romance for her is under the radar.

June 2023: Mellencamp opens up about her famous ex in a ‘What I Learned’ essay for Squire. First, he gives rare insight into their relationship when the first reunited, 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 things for us. We were so lost. We didn’t know how to do anything. I’ve never left a hotel by myself. She 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 have to put it in this thing,” and we said, ‘So what’s going on?’ We laughed at our stupidity, we cried so much. I think she learned to do everything and I learned 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 that much. She’s a great girl. I’m all also ** ** my boyfriend.”

To be continued…

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