'80s Throwback: Cozy Pics Of Cher & Tom Cruise During Their Hush-Hush Fling

As one of Hollywood's older icons, Cher's relationship history is well documented. In the mid-'60s, she married fellow musician Sonny Bono, and their duo paved the way for Cher to transform into a successful solo artist. She met her second husband, Greg Allman, while she was divorcing Bono in the '70s, but their marriage was as intense and short-lived as lightning.

Cher went on to date multiple famous men after her second divorce, including actor Tom Cruise. The two met at Madonna and Sean Penn's wedding in 1985, and they later bonded over having dyslexia at a Washington, D.C., event for people with learning disabilities. It looked like the chemistry between Tom Cruise and Cher was growing in photos from that 1985 event shared to X. Cruise was 23 and adjusting to fame, thanks to the movie "Risky Business," but looked comfortable standing right next to Cher, a more established entertainer at 39. The actor even said something to make Cher smile in the image on the right. Of that night, Cher said to Daily Mail's Event column in 2018, "We didn't go out till way later, but there definitely was a connection there."

Cher and Tom Cruise during a ceremony at Hecht's Metro Center store where they received the Outstanding Learning Disabled Achiever Award from the Lab School of Washington, 1985 pic.twitter.com/tSvc708iRD

— cinesthetic. (@TheCinesthetic) May 31, 2026

Cher and Cruise's discreet relationship was brief, reportedly because of their demanding careers. She fondly recalled her time with Cruise on a 2008 episode of "The Oprah Winfrey Show," and the clip resurfaced on TikTok in 2021. When asked about her date with Cruise, the singer said, "Oh that was a long date," and referenced the duo living together. She added, "He was so wonderful, and I was so crazy about him. And he was so different. He was a shy boy; he didn't have any money."

The secrecy of Cher's fling with Tom Cruise makes it one of her most interesting age-gap relationships, but the singer has shared some details over the years. Five years after her interview with Oprah Winfrey, Cher made an appearance on "Watch What Happens Live!" with Andy Cohen. When asked about the prowess of her lovers, she couldn't say exactly who was the best. "Well ... a lot of 'em kinda came in first," she remarked. "I've had just the greatest lovers ever." Cohen then asked about Cruise's ranking, and Cher revealed that her former beau did pretty well. She said, "He was in the top five," and that, "Well, it was pretty hot and heavy for a little minute" (via E! News).

In 1987, Cruise married fellow actor Mimi Rogers. Although the marriage occurred nearly two years after meeting Cher, Cruise and Cher remained on friendly terms since going their separate ways. In 2002, they were photographed smiling and hugging at a concert fundraiser. During Cher's appearance on Oprah Winfrey's show six years after that, she had nothing but nice things to say about Cruise and mused about what might've happened if circumstances were different: "It could have been a great big romance because I was crazy for him" (via Daily Mail).