Inside Tom Cruise and Cher’s 16-Year Age Gap Romance — And Why They Split

File this under celebrity pairings you never thought were real but absolutely were: Tom Cruise and Cher dated in the mid-80s. Yep. A 23-year-old Cruise, just off Risky Business, and 39-year-old Cher, already Cher, had a brief, very real thing that the public barely clocked at the time.

How this even happened

They first crossed paths at Madonna and Sean Penn's Malibu wedding in August 1985. The actual spark came a little later, at a White House event that October for guests with dyslexia. Both Cher and Cruise are dyslexic, and that shared experience clicked fast. Cher has said that behind the movie-star swagger, he was shy and self-conscious back then. She once told a story about a dinner where a waitress who had ignored him in school suddenly wanted his attention now that he was famous — it stuck with her (she talked about this to Cosmopolitan).

The 'long date'

What followed was not some casual fling. Cher says once they started seeing each other late in 1985, it got serious quickly.

'That was a long date — I lived in his apartment.'

She told that to Oprah, and she has kept the receipts over the years. On Watch What Happens Live in 2013, she called Cruise 'a great guy' and 'lovable' and summed up the vibe as, yes, pretty intense for a bit.

'He was in the top five. It’s not a long list. It’s just a good list.'

That top-five comment was to Andy Cohen, and she meant it as a compliment. She has also said, more than once, that under slightly different circumstances, it could have grown into a 'great big romance.'

Timing is a menace

So why did it end? Not drama — logistics. The window between Cruise's post–Risky Business rise and his next big leap slammed shut. As Martin Scorsese's The Color of Money geared up, production moved to Chicago early 1986. Cher could not uproot and follow, and that was that.

'I couldn’t go to Chicago and that was kind of the straw that broke the camel’s back.'

For reference, The Color of Money started filming in Chicago in January 1986 — right as Top Gun was about to rocket him into the stratosphere. They split, stayed friendly by Cher's account, and she has continued to speak well of him personally. She has also been frank about not understanding his later involvement in Scientology, telling the Daily Mail in 2018: 'I don’t get what he does, that whole Scientology thing.'

The quick recap

• August 1985: First meeting at Madonna and Sean Penn's Malibu wedding.
• October 1985: Real connection at a White House event for guests with dyslexia; both share that diagnosis.
• Late 1985: They start dating; Cher says she essentially moved into Cruise's place.
• Early 1986: Breakup when Cruise heads to Chicago for The Color of Money (shoot began January 1986).
• 1986: Top Gun explodes; Cruise becomes Cruise.
• 1987: Cruise marries Mimi Rogers.
• 2008–2013: Cher opens up about the relationship on Oprah and Watch What Happens Live, calling it 'pretty hot and heavy' and ranking him in her top five.
• 2018: She reiterates they remained on good terms but says she does not understand his Scientology tie.

Why this one sticks

It is a weird little time capsule: an already-legendary Cher and a pre–Mission: Impossible Tom Cruise bonding over dyslexia, keeping a very adult relationship surprisingly quiet, then losing out to the calendar. No scandal, no messy fallout — just two A-listers hitting the same green light at the exact wrong time.