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.