Cher is now 61, Cruise 45 and the dated was when Cruise 20.
Cher says she dated Tom Cruise when he was a 'shy boy'
The singer-actress discussed the relationship on an episode of "The Oprah Winfrey Show" taped Saturday in Las Vegas before a crowd of 4,000 people, according to Harpo Productions.
Winfrey plans to feature Cruise during episodes airing Friday and Monday. She told Cher that when she was at Cruise's Colorado home recently, the actor stressed that Winfrey should say hello to Cher for him."So how much of a date was that?" Winfrey asked, according to advance remarks released Wednesday by Harpo Productions.
"Oh, that was a long date," Cher said. "Really. I lived in his apartment."
"He was so wonderful. And I was so crazy about him," said Cher, an Oscar, Emmy and Grammy winner who has released 25 albums that have sold more than 100 million copies. "And he was so, like, different. He was a shy boy. He didn't have any money."
It was unclear from the remarks released by Harpo exactly when the relationship took place.
But in a similar interview in February to "Entertainment Tonight" Cher indicated it was after Cruise made "Risky Business," in 1983 but before "The Color of Money," in 1986. She also talked about the relationship in February to "Good Morning America." ( from the AP-Chicago).  
For the full talking about Cher and Cruise ,i also enclosed some information below , and continued on the next post. CHER WHO's ? She is, by Garrett's analysis, more of a stylist than a singer, and almost as much a personality as an actress, almost a modern-day Helen Morgan (Showboat, etc.) with better luck in life and career. Born: May 20, 1946 in El Centro, CA Avg.User Rating: 3893 RatingsRate this artist:
Genre: Pop .Styles: Classic Pop, Adult Contemporary, Pop/Rock, Folk Rock, Soft Rock, Rock, Spoken, Dance, Club/Dance, Dance Pop, Vocal Jazz, Oldies
CHER BIOGRAPHY ( from MSN Entertainment source) 
SONY and CHER  Cher has had three careers that place her indelibly in the public consciousness, and two have been in association with her then-husband, composer/producer/singer Salvatore "Sonny" Bono (February 16, 1935-January 8, 1998). She charted major hit records in the 1960s and 1970s, working in idioms ranging from early-'60s girl group-style ballads to Jackie Deshannon folk-influenced pop, to adult contemporary pop in the manner of later Dusty Springfield. She also embarked on an acting career, initially in the late 1960s in association with her work as part of Sonny & Cher but later on her own, which led to a series of increasingly polished and compelling performances in Silkwood, Mask and Moonstruck, for which she won the Academy Award for Best Actress.
Cherilyn Sarkisian was born in California in 1946; she was 17 when she first met Salvatore "Sonny" Bono, a songwriter and protégé of producer Phil Spector. Bono brought her to Spector, who used her as a backup singer and produced one single by her, a novelty Beatles tribute record called "Ringo I Love You" issued under the name Bonnie Jo Mason. It disappeared without a trace, but the couple were undaunted -- they emerged as a duo, initially called Caesar & Cleo, later that year, and cut "The Letter," "Do You Wanna Dance" and "Love Is Strange."
Caesar & Cleo didn't trouble the chart compilers with any degree of success, but late in 1964, Cher (then known as Cherilyn) was signed to Liberty Records' Imperial imprint, and Bono came along as producer. A Spector-ish version of "Dream Baby" managed to get airplay in Los Angeles, becoming a local hit, and they suspected they were onto something. That same month, Sonny & Cher, as they were now known, signed to Reprise Records and released their first single, "Baby Don't Go." The song became a major local hit in Los Angeles, after which the duo jumped from Reprise to the Atco label, a division of Atlantic Records. In April 1965 their first single, "Just You" was released and rose to number 20 on the charts. The duo was on its way, and Cher also had Imperial Records after her for a second single. The couple had seen the Byrds pioneer commercial folk-rock with Bob Dylan's "Mr. Tambourine Man," and had witnessed them performing another Dylan number, "All I Really Want to Do" at a club in Los Angeles. The group intended to issue their own recording of "All I Really Want to Do," but Cher, with Sonny producing, beat them to the punch with her own recording of the song.
In 1974, it was revealed that the couple's marriage was coming to an end. Ironically, Cher came out of this split more secure than her husband, despite his having guided her career for a decade and having all of the real training in the entertainment business. She embarked on an acting career, even as she continued to make headlines for her romantic exploits, including an affair with (and two marriages to) Gregg Allman. She became a far better actress than she was a singer, first revealed in Mike Nichols' Silkwood (1983) and then in Peter Bogdanovich's Mask (1985) and George Miller's The Witches of Eastwick (1987). Her acting peers caught on to the worth of her work in time for an Academy Award for Best Actress for her performance in Norman Jewison's 1987 romantic comedy Moonstruck.
Since the mid-'70s, Cher has been known more for her acting than for her music, although she has continued to record for numerous labels, including Columbia, and in 1998 scored an international chart-topping smash with the club-friendly single "Believe." She is, by Garrett's analysis, more of a stylist than a singer, and almost as much a personality as an actress, almost a modern-day Helen Morgan (Showboat, etc.) with better luck in life and career. ~ Bruce Eder, All Music Guide  |
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I bet there are still men in their teens and 20's who will gladly date Cher :)