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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.

“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.

Scroll below for a timeline of John’s dating history.

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