John Mellencamp’s Dating History! Singer’s Romances From Meg Ryan to Natasha Barrett

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, a source told Us Weekly that the actress had “no regrets.”

She will always love John, and really, she’s not laying any of the blame at his feet,” another insider added to 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 May 2021, Page Six reported the music legend and the blonde beauty became a pair earlier in the year, but Closer broke the news of their breakup several months later in August. Fortunately, the insider told Closer the two remain amicable.

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