Meg Ryan and John Mellencamp first dated for three years before calling it quits in August 2014 — and then becoming engaged

Meg Ryan and John Mellencamp have called off their engagement one year after announcing plans to wed, PEOPLE confirmed Monday.

The split adds another chapter to the pair’s rollercoaster relationship that dates back to 2011.

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Rumors swirled about the former couple when the When Harry Met Sally actress, 57, was seen without her engagement ring from the rocker, 68, while recently attending the Governors Awards. She was spotted the next morning without the ring while running errands in Los Angeles.

The pair became engaged last year after beginning to rekindle their romance in May 2017. The two first dated for three years before calling it quits in August 2014.

A New Year’s Romance

The actress and singer began dating in late 2011, with PEOPLE confirming the two were seeing each other in January 2011 after Mellencamp split from his wife of 18 years, Elaine Irwin.

The couple was spotted together at Martha’s Vineyard and New York City, enjoying a coffee together and even going grocery shopping — where observers told PEOPLE at the time the two looked happy and at ease.

Image zoom John Mellencamp and Meg Ryan Alo Ceballos/FilmMagic

Separated by Distance

But they called it quits in 2014.

A source told PEOPLE at the time “it was the distance” that separated them. “She lives in New York and he resides in Indiana,” the insider said. “It was the long distance that ultimately was the cause.”

Mellencamp previously expressed his unhappiness with living in the Big Apple.

“I’m too sensitive to live here,” he told Rolling Stone in December 2013. “I can’t see poor people. I can’t see suffering. I can’t see the trash on the streets.”

When it came to the paparazzi, the “Jack and Diane” singer said, “I don’t give a f— about me, but I don’t like it for [Ryan].”

His true home was Indiana, he added. “I’m not leaving Indiana,” he said. “I’m going to die here.”

No Hard Feelings

One month after their split in 2014, Mellencamp couldn’t help but gush about the Sleepless in Seattle actress.

He spoke about her during an interview in Sirius XM’s The Howard Stern Show, saying, “Meg is an angel. She was just an angel sent to me at the right time.”

Image zoom Ryan and Mellencamp taking a stroll in New York City Splash News

“We tried to have a relationship for three years long distance,” he continued. While the distance was what broke them apart, Mellencamp hinted there could still be a chance of a reconciliation.

“We’ll see what happens,” he said.

The “Hurts So Good” singer eventually moved on and began dating model Christie Brinkley for about a year before the two split in 2016.

As for Ryan, she told Closer in 2015 she was “taking a little break” from relationships.

“I’m [in love] with my life right now in a way that I adore, with my kids and my world,” she said. “I love my age. I love my life right now. I love what I know about. I love the person I’ve become, the one I’ve evolved into.”

She added, “In my life, I’ve been scrappy as hell, but I feel easy with things now. I think that comes with age.”

“She Hates Me to Death”

While it seemed things between the two were amicable, Mellencamp opened up about the actress again in an interview with Howard Stern on his Sirius XM show in March 2017.

“Oh, women hate me,” he said. “I loved Meg Ryan. She hates me to death.”

When Stern asked why Ryan would “hate” the singer, the rock star elaborated, “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.”

Image zoom John Mellencamp, Meg Ryan and Jack Quaid attend the New York Knicks Vs Philadelphia 76ers game on December 25, 2017 James Devaney/Getty

Mellencamp revealed he tried to make amends with the Kate & Leopold actress, saying, “I’ve done that. She just doesn’t want anything to do with me. And I can’t blame her.”

“They Have a Bond”

In June 2017, two months after the rocker insisted the actress “hated” him, the two were photographed together at the Art Cliff Diner in Martha’s Vineyard.

One month after their outing, a source told PEOPLE the two were back together, saying, “They have a bond.”

The couple had been steadily dating until the actress announced their engagement in 2018.

Ryan actress shared the happy news on her Instagram account, writing, “ENGAGED!” next to a sweet and silly cartoon drawing of the two reaching for each other’s hands.

“He Didn’t Want to Get Married”

On Monday, PEOPLE confirmed the pair had called it quits one year later. Us Weekly was the first outlet to report the news.

“He didn’t want to get married again,” a source told PEOPLE. (Mellencamp has been married three times before.)