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The Monkees Mike Nesmith was 44 when he met 15-year-old Winona Ryder, the star of a film he produced titled Square Dance. Despite their large age gap, they forged a friendship. However, Nesmith felt more than friendly toward the young actor, who only had one acting credit to her name, Lucas, before working alongside The Monkees songwriter and guitarist. He once said he was “madly in love” with the current Stranger Things star and admitted, “I couldn’t say no to her.”

Former 'The Monkees' star Mike Nesmith and actor Winona Ryder.
Mike Nesmith and Winona Ryder | Ron Galella Collection via Getty Images

Mike Nesmith and Winona Ryder met in 1986

Square Dance producer Dan Petrie could only come up with half the funding needed to begin shooting the low-budged film starring Ryder, Rob Lowe, Jane Alexander, and Jason Robards, reported The LA Times.

The film tells the story of a 13-year-old country girl (Ryder) who moves to the city and becomes emotionally involved with an intellectually disabled 21-year-old man (Lowe).

Petrie would find the remaining funding from Nesmith’s Pacific Arts production company and former NBC executive Brandon Tartikoff.

It was during his involvement with the project that Nesmith met Ryder, and their brief relationship began.

Mike Nesmith was quoted as saying he was ‘madly in love’ with Winona Ryder when he was 44, and she was 15

Winona Ryder and Mike Nesmith attend a movie premiere in 1987.
Winona Ryder and Mike Nesmith | Ron Galella Collection via Getty Images

‘The Monkees’: Mike Nesmith’s Embarrassing On-Screen Slip Caused Frank Zappa to Laugh Out Loud

In the late 1980s, The Monkees experienced a career resurgence. Original members Micky Dolenz, Peter Tork, and Davy Jones took the band on the road twenty years after the group’s hugely successful debut.

However, Mike Nesmith opted out of performing with The Monkees. But that didn’t mean he didn’t attend one of the band’s shows with Ryder in tow.

Harold Bronson’s book “Hey, Hey, We’re the Monkees” featured quotes from Nesmith regarding his relationship with Ryder.

The blog The Monkees Live Almanac excerpted the passage.

“I was producing a movie called Square Dance in Texas,” Nesmith explained.

“It was a starring part for Winona Ryder, who was about fourteen or fifteen. She said, ‘aren’t The Monkees going to play in Arlington?’ which was just up the road from where we were filming,” the songwriter shared.

Ryder asked if Nesmith would take her to the show. He refused, saying, “Nonie, I am one of The Monkees. I can’t show up with you going to a Monkees concert.”

The actor reportedly pressed Nesmith to escort her to the show.

Nesmith then admitted he had deep feelings for Ryder.

“I was madly in love with her. She was such a wonderful young girl. 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,” Nesmith shared.

Nesmith escorted Ryder to The Monkees’ concert undercover

Additionally, Nesmith explained that after securing two “ordinary” tickets to see the performance, he went to the costuming department of Square Dance. There, he came up with a disguise.

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

He added a pair of glasses and a baseball hat to complete his costume.

Nesmith and Ryder attended the concert, sitting among other fans.

He later explained he enjoyed watching the show from an outside perspective and experiencing the give and take between the three performing band members and the audience.

However, Nesmith explained his experience as a member of The Monkees was very different.

“I was trying to play loud enough so I could be heard,” Nesmith deadpanned.

“I think Nonie liked it as well,” he said of what he believed to be Ryder’s show experience.