John Mellencamp's Dating History: Meg Ryan, Christie Brinkley

Singer John Mellencamp has dated a few lovely ladies during his decades-long career in the entertainment industry. Whether it be a short fling with a girlfriend or a long marriage, the star has learned a lot about love. But even though he has dated some really great people, one of his most memorable romances is with legendary actress Meg Ryan.

The former lovers dated on-and-off for nearly a decade until 2019. During their time together, John and Meg intermixed their kids, creating one of the sweetest blended families in all of showbiz.

“They are such an amazing couple,” John’s daughter Teddi Mellencamp exclusively told Closer in February 2019. “They are both smart and funny. Their conversations are interesting and like watching a ping-pong match. They really bring out the best in each other — like all good couples do.”

Sadly, it didn’t last between the crooner and the When Harry Met Sally star. In October 2019, the two called off their engagement. Although it was heartbreaking for the former pair to officially end their romance, they seemingly remained amicable.

“She will always love John, and really, she’s not laying any of the blame at his feet,” a separate insider told Closer about the exes shortly after the news of their breakup was revealed. “He has to be who he is, but very importantly, Meg has to main her own vision, her own identity and plot out her life the way she feels is best. And right now, she feels it is best they go their separate ways.”

Since ending their relationship, John has been keeping busy in the dating department. In March 2020, he “moved on” and “found love again” with beauty expert Nurse Jamie Sherrill, a source told Closer. Even though things seemed “pretty serious” between the two, Page Six reported they went their separate ways less than a year later in January 2021.

Following his split from Jamie, John was romantically linked to a realtor named Natasha Barrett in 2021. Closer broke the news of their breakup several months later in August, noting that the two remain amicable.

For a complete timeline of John’s dating history through the years, scroll through the gallery below!

Meg Ryan

Meg and John have a whirlwind romance. After they initially got together in November 2010, they stayed together for four years before breaking up in August 2014. However, they couldn’t stand being apart from one another because they got back together before the end of that year.

In October 2015, they called it quits again. The couple stayed separated until July 2017. Once they decided to give their romance another shot, they broke up again when they called off their engagement in 2019.

Jamie Sherrill

John and Jamie became a couple in early 2020 and dated for nearly a year. Things appeared to be going well for the two, with Jamie introducing John “to her triplets,” a source told Closer. They were even “staying at his place in Bloomington, Indiana,” amid the coronavirus pandemic together. However, Page Six reported the two quietly split in January 2021.

Natasha Barrett

The “Ain’t Even Done With the Night” singer became involved with Natasha shortly after he called it quits with Jamie in early 2021, per Page Six. Though it’s unclear exactly when the two started dating, the outlet reported they were already romantically involved “for the past few months” when they were spotted holding hands on the beach in May. John and Natasha were all smiles as they made their first public appearance as a couple in Malibu over Memorial Day weekend.

Just months later, however, a source told Closer the two ended their relationship. Despite the breakup, the insider insisted the “Pink Houses” artist and the realtor are on good terms.

Marianelly Agosto

After his split from Natasha, John opened his heart to find love again. The “Small Town” singer revealed the qualities he was looking for in a future partner during an October 2021 interview with Extra.

“I don’t care what anybody does. I don’t care how much money the person’s got. Is she a nice person? Is she funny? Can she stand John Mellencamp?” he said at the time.

He began dating Marianelly Agosto in 2022. A source told Us Weekly that the hitmaker and the skincare expert were introduced by John’s daughter Teddi. The couple, who have a 27-year age gap between them, have been dating “on and off” but have been back together since August 2022.

Though Marianelly’s Instagram account is private, she revealed in her bio that she is a mother and has a passion for skincare. She currently works for a company called Active Skin, according to her LinkedIn profile. She previously worked as an esthetician at Hylunia Skin Care and Allure Laser Medi Spa.

In November 2022, the beauty supported her beau as he gave a speech at the Rock and Roll Hall of Fame induction ceremony. The couple posed for photos with Teddi and her husband, Edwin Arroyave, at the event. That same month, John and Marianelly stepped out together for a concert at Lincoln Center in New York City. They held hands as they made their way into the venue wearing coordinating black outfits.