Inside Mike Nesmith and Winona Ryder’s Relationship

It’s no surprise that men in Hollywood are known for lusting after women much younger than them — just take Leonardo DiCaprio and his affinity for 20-year-olds for example. However, every once and a while, a “relationship” between two celebrities happens in which their age gap is so questionable that it’s hard to call it a relationship in good faith.

That’s certainly the case between Winona Ryder and The Monkees’ Mike Nesmith.

In quotes from Mike that were written into a book about his band, Mike admitted to being “madly in love” with Winona while they worked together on the film Square Dance. The only problem? He was 44, and she was only 15.

Stranger Things star and Tim Burton muse Winona Ryder is beloved by many, but back in the ’80s, musician Mike Nesmith certainly took things too far.

The two met back in 1986 when Mike was involved in the production of a film called Square Dance, which starred a young Winona as a 13-year-old country girl who becomes romantically involved with an older man.

Winona was new to the acting scene at the time, with only one other credit under her belt, and Mike took a liking to the burgeoning actor. In quotes from the book Hey, Hey, We’re the Monkees, written by Harold Bronson, Mike explained his fondness for her.

“I was madly in love with her. She was such a wonderful young girl,” he reportedly said. “There’s a certain age at which young women blossom. They have a puppy quality about them, very fetching. She was right at that age. I couldn’t say no to her.”

At one point, when The Monkees experienced a resurgence in popularity in the ’80s, the band performed a reunion concert. Though Mike did not participate, he did attend the concert — with Winona as a guest.

“She said, ‘Aren’t The Monkees going to play in Arlington?’ which was just up the road from where we were filming,” Mike said. He initially refused to take her, knowing that it would look inappropriate on his part, but he eventually gave in. However, he used a disguise so as not to be recognized by the crowd.

“From the costume department, I got a fat pad and grayed my hair and beard,” he explained. “I think Nonie liked it.”

Though the late musician has been credited by some for launching Winona’s acting career, many others have criticized him for his alleged inappropriate relationship with the teen.

“Not condoning ANY of this,” one user on X (formerly Twitter) said, “but the state of California and the U.S. in general have the worst statutory laws, thus making stuff like that more easily acceptable by the mainstream in those times.”

Another wrote, “Do you think Winona is another victim of child acting? How come she hasn’t come forward with any “Me too” moments? She seemed mentally unstable for a long time, and yet no one really asked why, like we did with Britney [Spears].”