Cher was "crazy" for Tom Cruise when the couple dated.
The singer said her brief relationship with the actor in the 80s could have been a "great big romance" if their hectic schedules hadn't forced them apart.
Cher - who was 39 when she dated then 23-year-old Cruise - said: "I was crazy about him. He was shy. He said he felt like such a boob in school and nobody talked to him. We went on a date once for dinner in a New York restaurant and the waitress was from his old school.
"He told me she never talked to him back in school, but now he was recognised he got all her attention. It could have been a great big romance because I was crazy for him."
The affair - which is believed to have started when the pair met at a fundraising event in the White House - ended after several months when Tom met actress Mimi Rogers, who he later married.
Cher - who has been married twice - told US talk show host Oprah Winfrey she is currently single, because men find it difficult to deal with her fame.
She added: "Dating is a strange thing. It's not every man who can be comfortable with me. Being Cher is a hard thing and difficult for him to hold his place."
Tom, 45, divorced Mimi in 1990 after three years of marriage. He later married Nicole Kidman, who he split from in 2001 after 11 years of marriage.
He wed Katie Holmes - the mother of his two-year-old daughter Suri - in 2006.
Cher, 61, was married to musician Sonny Bono from 1964 to 1975. She later married singer Gregg Allman, who she divorced in 1979 after four years of marriage.
- BANG! SHOWBIZ