Odd Couples: Surprising Star Pairs You Never Knew Dated!

No joke: young funnyman/future Tonight Show host Jay Leno and 25-year-old Sharon Osbourne had what she labeled as a "flingywingy" after they met one evening in a bar in the 1970s.

TV chef Padma Lakshmi had lost her partner, billionaire Teddy Forstmann, to brain cancer in 2011, and after a tough period of deep mourning, Richard Gere was the first person she dated.

"Richard is a really nice, sweet man and he was the first person I dated after Teddy and he was very nice to [my daughter] Krishna," she said.

It only lasted a short time, though.

S-- and the City and Iron Man were in the distant future when Sarah Jessica Parker and Robert Downey Jr. began dating in 1984 when they were both 18-year-old dreamers.

Parker described the relationship as "era-defining but doomed." They spent seven rocky years together, but his troubled drug abuse finally did the relationship in.

Jake Gyllenhaal and Taylor Swift dated in 2010 and lasted only a few months. Many fans believe her song "All Too Well" was inspired by their age difference (29 and 20) during their time together.

But Gyllenhaal said, "It's got nothing to do with me."

In 2002, Sandra Bullock fell for future Fall Guy Ryan Gosling — long before he became Just Ken to Barbie. The Gravity actress said he had a way of bringing her back down to earth, saying that he taught her "to chill … He's like a little Buddha."

They only lasted a year, but Gosling said Bullock was one of his "greatest girlfriends of all time."

After Nicole Kidman's divorce from Tom Cruise, Lenny Kravitz was her first serious relationship. They dated for about six months and stayed great friends afterward.

Cher and the Top Gun star hit it off back in 1985 when they met at the wedding of Madonna and Sean Penn. The singer said Cruise still rates as one of her top five best lovers!

"It could have been a great big romance, because I was crazy for him," she insisted.

Among lover boy Brad Pitt's many romances was one with National Lampoon's Christmas Vacation beauty Juliette Lewis, who was 17 when she started dating the 26-year-old actor in 1989.

"He's not in my universe at all now," she said. "It seems like a high-school relationship because now he's a very famous person."

E.T. star Drew Barrymore was 10 years old when she first went out with 14-year-old Corey Feldman in 1985, but they actually started dating four years later.

Back in 2001, before Chris Evans became Captain America and Jessica Biel met and married Justin Timberlake, these two dated for around five years.

Macaulay Culkin was no longer "home alone" when he and then unknown That '70s Show siren Mila Kunis started a relationship in 2002 that lasted eight years.

Kunis said the actor was "probably the most brilliant person she ever met," adding he was "so, so smart and so aware and so kind and so sweet."

Neither Lisa Kudrow nor Conan O'Brien knew that the other would become mega-famous when they had a short relationship after meeting in an improv comedy class before Friends debuted.

She said, "He's one of the funniest people I know."

Jennifer Aniston fell under the spell of Love Potion No. 9 hunk Tate Donovan from 1995 to 1998, and said he was "the perfect guy" during their time together. Even after he ended it, Aniston said he was a "wonderful guy."