Diane Keaton and Keanu Reeves
Dated 2005
They played lovers in 2003's Something's Gotta Give, but had a real life romance two years later when Keaton was spotted visiting Reeves' LA house for a series of late night trysts. And Keanu, 47, who has dated Winona Ryder, Cameron Diaz and Sandra Bullock, reportedly even dumped then-girlfriend, Wolverine star, Lynn Collins, so he could date 66-year-old Diane.
Courteney Cox and Michael Keaton
Dated 1989-1995
The Cougar Town actress started dating the actor when she was an unknown 24-year-old and the Beetlejuice and Batman star was 37, with the romance lasting for six years. When asked why they split up, Cox said she didn't want to go into it because Michael is "a very private person," but that they "weren't right for each other ultimately." Adding, "I was too young to know what I needed in a relationship."
Jennifer Aniston and Adam Duritz
Dated 1995
The 43-year-old unlucky in love actress dated the big-haired Counting Crows frontman for just a few months back in 1995, at the start of her Friends fame; with the Mr Jones singer reportedly moving onto Jen's BFF and co-star Courteney Cox right after they split. Duritz has hinted that the relationship wasn't all smooth sailing, explaining, "Some people you really dream about dating, then, when you get there, you think, ‘Wow, this is not the vacation I thought it would be. This is not where I want to spend my vacation.'"
Tom Cruise and Cher
Dated 1986
Singing and acting legend Cher admitted she had a relationship with Tom Cruise when he was 23 and she was 40, but said they broke up due to distance and conflicting schedules. "When we were together he was such a private person," she revealed. "He always has been until lately" - referring to his couch-jumping, early Katie Holmes days. Adding, "I loved him though, he was amazing. It's now hard for me to look at this person and this press. How many times can I watch him jumping up and down on Oprah's couch?"
Brad Pitt and Sinitta
Dated 1987-1989
During the height of her late Eighties fame, UK-based American singer, Sinitta, 43, (probably best known as Simon Cowell's ex and for her hit, So Macho) dated then unknown actor Brad Pitt for two years. "He was fun, he was young and very sweet," she recently spilled. "He was beautiful and had the most amazing body."
Wesley Snipes and Jennifer Lopez
Dated 1994
Back when Forbes' current ‘Most Powerful Celebrity' was just a fledgling actress, J-Lo briefly dated her Money Train co-star, Wesley Snipes, and has said that he took it very personally when they split, insisting, "He wouldn't talk to me for two months. I was like, ‘What an *******'. Actors are used to getting their way."
Vanilla Ice and Madonna
Dated 1991
One-hit wonder rapper, Vanilla Ice, dated her Madgesty back in the early Nineties, but says he broke it off with her after her explicit book, Sex, was published. "Going out with Madonna was exciting," he revealed. Adding of the 10-year age gap, "She's still the oldest person I've ever been with, so it was an experience. But I broke up with her after she printed that book because… it was disgusting and cheap… she threw me in like I was a product off a shelf and I didn't appreciate it."
Kim Kardashian and Nick Lachey
Dated 2006
Six months after his divorce from Jessica Simpson, singer Nick Lachey dated then unknown "stylist" Kim Kardashian. The pair was spotted holding hands and hanging out at exclusive industry parties, and an inside source at the time said Nick liked Kim because she was, ahem, "smart and not an actress and couldn't care less about the Hollywood scene." Ha!
Glenn Close and Woody Harrelson
Dated 1991
The Damages actress dated Harrelson when he was the 29-year-old cute guy from Cheers and she was the 44-year-old femme fatale from Fatal Attraction. And a tell-all book by Hollywood screenwriter Joe Eszterhas, has suggested their brief relationship was very steamy, revealing, "Glenn couldn't get enough of Woody."
Kelly Preston and George Clooney
Dated 1987-1989
The acting superstar met Kelly Preston - who has been married to John Travolta for 21 years - at acting school in Beverly Hills, when George was a mere bit-part actor in TV soap The Facts Of Life. They were together for two years and lived in a Hollywood Hills home with their pig, Max, and George was reportedly "devastated" when she left him for Charlie Sheen, and insisted that he keep their potbellied pet.
Ryan Gosling and Sandra Bullock
Dated 2001
The pair dated for a year, with Gosling calling Sandra "the greatest" post-split. Sandra did get teased for their 16-year age difference though, and her friend Hugh Grant admitted he used to call Gosling, "The Child". "I'd make the sound of a baby crying," he said. "And she'd know who I meant."
Eva Longoria and JC Chasez
Dated 2005
The 'N Sync singer and Desperate Housewives star dated for around eight months after they met while bidding on the same dog at a charity auction, with the actress later dumping him for Get Carter director, Stephen Kay.
Jessica Simpson and Billy Corgan
Dated 2009
New mum Jessica Simpson, 31, dated the Smashing Pumpkins frontman, 45, after her relationship with Dallas Cowboys star Tony Romo hit the skids, with sources spilling it was his "pure" spirituality that attracted her.
Heidi Klum and Anthony Kiedis
Dated 2002
The supermodel and the Red Hot Chili Peppers singer were spotted cuddling in Sydney and riding around on motorbikes together when they dated for a few months in late 2002, following her divorce from her first husband.
