The Truth About John Mellencamp's Relationship History

He's been making music since the 1970s under a variety of names, including John Cougar, John Cougar Mellencamp, and finally just John Mellencamp. His breakthrough hit came in 1982 with the classic tune "Jack and Diane," a story about love, life, and how life can get in the way of love. Mellencamp's love life has had its own fair share of love song angst to it. As of this writing, Mellencamp has a new woman in his life and a fascinating relationship history that led up to her.

Mellencamp was born on Oct. 7, 1961, in Seymour, Indiana, and by his teens he was playing in a cover band — and already a father. The musician eloped at age 18 with his 21-year-old girlfriend, Priscilla Esterline, and they soon welcomed a daughter named Michelle. Although he did attempt to earn a college degree to help support his young family by attending Vincennes University, it always came back to music for him, according to Biography. While he remained married throughout the 1970s, by 1981 Mellencamp and Priscilla divorced right before his career took off.

John Mellencamp's longest relationship

By the 1980s, John Mellencamp's star was on the rise and he was on to his second marriage to Victoria Granucci. The pair remained married until 1989 and welcomed two children, Teddi and Justice, according to Closer Weekly. Teddi is now all grown up and a star in her own right. Known as Teddi Mellencamp Arroyave, she has made a name for herself as one of the stars of "Real Housewives of Beverly Hills" (via Bravo TV).

Just because Mellencamp's first two marriages didn't last, it didn't mean the singer was gun shy as he embarked on his longest relationship to date when he married model Elaine Irwin in 1992. That union produced two sons, Speck and Hud, and lasted nearly two decades until the pair split in 2011. Not long after, Mellencamp embarked on a high-profile romance with one of Hollywood's most famous leading ladies, Meg Ryan (via Closer Weekly).

His on-again/off-again romance with Meg Ryan

If there's anyone who knows how to do romance on screen, it's Meg Ryan. The actress starred in myriad classic rom-coms in the late 1980s and 1990s, including "When Harry Met Sally ...," "You've Got Mail," "Sleepless in Seattle," and "City of Angels" (via IMDb) before entering into a relationship with John Mellencamp in 2011.

Meg Ryan had another high-profile partner before Mellencamp, with her marriage to actor Dennis Quaid from 1991-2001. When she met Mellencamp, she was raising her two children, Jack and Daisy, and had only been making movies sporadically for several years (via Biography). Mellencamp and Ryan's romance put them both on the cover of tabloids, especially when they broke up in 2014 but then couldn't stay away from one another.

The two had a long-distance relationship with Ryan living in New York and Mellencamp back in his native Indiana. According to People, Mellencamp hated New York, so they split but always had good things to say about one another. Although the musician had a brief romance with former model Christie Brinkley in 2016 (via Closer Weekly), by 2017, Mellencamp and Ryan had mended fences and were back together. By 2018, they announced they were engaged. Sadly, the marriage never happened and the engagement was off by 2019 (via People).

John Mellencamp has a new love in his life

In early 2020, John Mellencamp seemed to find love again when his daughter, Teddi, introduced him to Jamie Sherrill (via Page Six), a nurse and celebrity skin expert who has appeared on such shows as "The Doctors," "The Today Show," and "Good Day LA." Mellencamp and Sherrill reportedly sheltered in place at his Indiana home, according to Closer Weekly, but broke up as the new year began.

Mellencamp was not alone for long, however. In June of 2021, Page Six reported that Mellencamp was dating realtor Natasha Barrett, and the two were spotted by paparazzi holding hands in Malibu. According to People, Teddi Mellencamp played matchmaker once again, as she introduced her dad to the latest lady in his life. It's been a life of music, marriage, children, and splits for John Mellencamp, but as of this writing, it looks like he hasn't given up on love.