Meg Ryan and John Mellencamp Engaged: Everything to Know About Their Rollercoaster Relationship

Meg Ryan and John Mellencamp are engaged but it hasn’t always been a smooth relationship for the two.

The 56-year-old actress shared the announcement on her Instagram account on Thursday, writing, “ENGAGED!” next to a sweet and silly cartoon drawing of the two reaching for each other’s hands.

The news comes after Ryan and Mellencamp, 67, rekindled their romance in May 2017. The two first dated for three years before calling it quits in August 2014.

While the two are now preparing to walk down the aisle, here are the ups and downs of their rollercoaster relationship.

A New Year’s Romance

The actress and singer began dating in late 2011, with PEOPLE confirming the two were quietly dating 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.

Mellencamp has been married three times before and has five children, including two sons with Irwin. Ryan has been married once, to actor Dennis Quaid. They have one son, Jack Henry, 26.

Separated by Distance

The two split in August 2014 after dating for more than three years.

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.”

While the pair was dating they kept a low profile, stepping out occasionally for industry events and being spotted every so often on the streets of New York City.

Despite their romance, 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.”

“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.”

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.”

Since then, the couple has been steadily dating until the actress announced their engagement on Thursday.

RELATED VIDEO: Meg Ryan and John Mellencamp Are Back Together: ‘They Have a Bond’

After the two reconciled, they were spotted together a few times and spent Christmas Day together with their two sons from previous relationships. The pair even caught a New York Knicks basketball game with her son Jack and Mellencamp’s 24-year-old son Hud from his marriage to Irwin.

The outing was a festive one for the blended family as Hud and Jack both dressed up in Christmas gear to celebrate the holiday while sitting courtside. Hud opted for a green shirt mimicking an elf’s uniform while Quaid went with a red, white and dark blue Christmas sweater with reindeer print.

Mellencamp and Ryan are now engaged with the actress announcing the news on Instagram just hours after photos surfaced of her out and about in New York City on Wednesday wearing an engagement ring.