Perhaps the only thing more shocking than the fact that these two dated (it was only one date in 1986) was what happened on that sole date. According to Couric, King drove her back to his place after dinner. "So we sat there, and what can I say, he lunged," Couric said on Jimmy Kimmel Live! "I love Larry, by the way. I do love him. But I started laughing a little bit because the whole situation was like out of a bad Lifetime movie."

Berry was hangin' tough with the New Kids on the Block singer at the height of the boy band's fame in 1989. Three years later, Berry wed baseball player David Justice.

Before Posh wed Becks, she dated a Lost Boy. The two met in 1995 at a London recording studio and Beckham even introduced Haim to her parents. In her autobiography Learning to Fly, Beckham said they broke up because Haim was jealous of her love of the boy band Take That and that she threw his belongings out of a hotel. Haim died in 2010.

The pair dated after meeting on the set of the 1998 flick Velvet Goldmine. Collette later detailed the rocky relationship on her debut album Beautiful Awkward Pictures and Rhys Meyers took the blame for the breakup, saying that he, at age 19 (five years younger than Collette) was not mature enough.

Who could forget those smooching-on-the-beach pics? The former Desperate Housewives star went on three dates with the American Idol host in 2006 before he ended things, saying, "I don't think I can do this with you," she later told Oprah Winfrey. "I don't know [why he did]. … I ate too much lobster?"

Do you believe in life after love with Tom Cruise? Cher did. The singer-actress, who's 16 years Cruise's senior, dated the Risky Business star in the mid-'80s and confessed to Oprah Winfrey that she was "so crazy about him."

After Cruise, Cher dated the Bon Jovi guitarist for a year in 1989. Sambora produced Cher's self-titled 1987 album.

The Happy Days heartthrob romanced his share of ladies back in the day, but none was more surprising than Liza Minnelli. The two had a May-December romance (she's 14 years older) in the mid'-90s and Baio later confirmed rumors that Minnelli wanted to have his baby.

Before Stedman, there was John Tesh. Oprah and the New Age musician/radio host dated in the '70s when they were cub reporters in Nashville. According to an unauthorized biography of Winfrey, the couple split because of the "social pressure" of their interracial relationship.

One thing's for sure, Sandra Bullock definitely does not have a type. In between dating Tate Donovan and Matthew McConaughey and marrying Jesse James, Bullock went out with Gosling, who's 16 years her junior, for a year from 2002 to 2003. The pair met on the set of Murder by Numbers.

The Terriers star and Modern Family bombshell dated briefly after meeting on the set of their 2007 ABC sitcom The Knights of Prosperity. They went public at the Ghost Rider premiere that year.

The techno DJ dated Portman in the 2000s and got some flack for it, or so he says. "I guess in some people's eyes, [nerds] might be mildly sexy — and, as a nerd, I'm certainly happy to enjoy some of the effects of that. But as far as the very brief affair that I had with Natalie, it's made me a target of a lot of nerd wrath," Moby told Spin in 2008. "You don't date Luke Skywalker's mom and not have them hate your guts."

Was it Fatal Attraction that brought them together? Close, who's 15 years Harrelson's senior, dated the Cheers star for a few months in 1991.

Before her three divorces, Bennifer and his imprisonment for tax evasion, J.Lo and Snipes dated in the mid'-90s after meeting on the set of their 1995 film Money Train.

Adam Duritz and Jennifer Aniston, Courteney Cox, Mary-Louise Parker and Emmy Rossum It might be hard to believe, but the Counting Crows frontman has wooed some of TV's top leading ladies, including Parker in the '90s and Rossum for a year in 2010. His most famous exes are real-life Friends Aniston and Cox. After dating Aniston in 1995, Duritz went out with Cox two years later. Cox also appeared in the band's music video for "Long December." What is it about this dreadlocked romeo? Ask them.

Long before either of them made it big, the pair dated in the late '90s when Fergie's girl group Wild Orchid opened for 'N Sync. "He was 16 and I was 23," Fergie recalled to Australia's Courier Mail. "It was right before he got real heavy with Britney [Spears]."