What? Cher and Scientology Wacko? Now why after all these years have passed would singer Cher admit to having a fling with Tom Cruise. Seriously, why? During an interview with the talk show queen Oprah Winfrey, Cher revealed that she was crazy for the Risky Business star.

The romance was back when Tom was a mere 23 and Cher was sixteen years his senior and a seasoned pro at 39. The singing icon told Oprah it could have been a BIG romance because she really liked him but she was too busy to pursue it properly. Whatever prompted her to ‘out’ Tom in such a bizarre way is actually humorous. She also said:

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 recognized and he got all her attention.”

Does Tom still feel like a boob from time to time? Probably so. For starters, the actor could use a stylist who would advise Cruise to dump the Mr. Rogers sweaters.

Cher is starting a new long term gig at Caesars Palace in Las Vegas, which may be why she let slip her fling with Cruise. Tom will be featured on Oprah’s Friday show, his first sit down interview with O since he jumped on her couch two years ago. The interview took place over the weekend at Telluride, his Colorado retreat.

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Filed under: Celebrities, Cher, Tom Cruise