“I love Meg Ryan,” he wrote. “I went with her for ten years. She doesn’t love me so much. She’s a great girl. I’m just a s–tty boyfriend.”
The “Hurts So Good” singer and the When Harry Met Sally actress began dating in 2011, after Mellencamp divorced from Elaine Irwin and 10 years after Ryan ended her marriage with Dennis Quaid in 2001. The couple broke up in 2014, before reconnecting at the end of 2017. By 2018, the “Jack & Diane” singer and the You’ve Got Mail star were engaged, though they split for good a year later.
“Meg Ryan had just come out of her shell; I had just come out of my shell,” Mellencamp recalled of their relationship’s start. “We started dating. And we decided to do things on our own instead of having people do stuff for us. We were so f—ing lost. We didn’t know how to do anything.”
He continued, “I’ve never checked out of a hotel by myself. Her and I went to a grocery store, and they wanted our credit card, and we looked at each other and said, ‘Here it is,’ and they said, ‘No, you’ve got to put it in this thing,’ and we went, ‘Then what happens?’ We laughed at how stupid we are, so hard we cried. I think she’s learned how to do everything, and I’ve learned how to do nothing.”
Read Mellencamp’s full “What I’ve Learned” essay here.