ByVaria Fedko-Blake, writer at
Staff Writer at Moviepilot! [email protected] Twitter: @vfedkoblake
Varia Fedko-Blake

We remember the flashy weddings and disastrous divorces, but we often forget that before celebrities chose to settle down (or break-up with their significant others), they also dated a slew of other famous faces.

You'll never believe the strange hookups and relationships that the following A-listers would rather leave locked up in a secure vault in the past.

Let's take a look!

1. Janet Jackson & Matthew McConaughey

Before he met his now-wife in an L.A. bar, Matthew had a slew of relationships with leading ladies, including Sandra Bullock, Penelope Cruz and Ashley Judd. Most surprisingly however, he also had a brief tryst with none other than Janet Jackson!

2. Shia LaBeouf & Hilary Duff

Hilary and Shia did indeed try to give it a go a few years back. Yet, unfortunately the experience ended in disaster and they agreed to move on. In fact, the actor lovingly described one date at a sushi restaurant as:

“Probably the worst date either of us has ever had.”

I'm sure Hilary was over the moon to hear that.

3. January Jones & Ashton Kutcher

Back when Ashton was just a dude looking for his car, he dated January Jones for three years from 1998 to 2001. According to the Mad Men star though, he wasn't a very good boyfriend, being very unsupportive of January's acting career. She told GQ in 2009:

"He was not very supportive of my acting. He was like 'I don't think you're going to be good at this.' So, f*ck you!"

I take it they're not on speaking terms today then.

4. Liam Neeson & Helen Mirren

Liam Neeson and Helen Mirren fell in love while filming Excalibur back in the '80s and dated for four years! Eventually, they grew apart and moved on. Speaking of her relationship with the actor, she once said:

"We loved each other, it was difficult to let go."

Liam also reportedly went out with Julia Roberts in 1987, hooking up after working together on Satisfaction when she was just 19 years old and he was 35! They even moved in together for a while, before calling it quits after a year.

5. Will Smith & Tyra Banks

Before Will began dating his now-wife Jada Pinkett, he was actually canoodling with Tyra for about a year after her appearance on The Fresh Prince of Bel-Air:

6. Paris Hilton & Val Kilmer

Although the above image is actually a film still from Wonderland, a movie the two stars appeared in, they also did date on the side. Notoriously, the 32-year-old was spotting making out with Kilmer, 53, back in 2002 at an L.A. nightclub, which confirmed their romance.

7. Winona Ryder & Charlie Sheen

Apparently, the two dated back in 1986, after meeting on the set of Lucas. The pair were so close that Sheen even claims to have given Winona her stage name. During an interview, he once revealed:

"We were listening to the Doors, to 'Riders on the Storm.' [Winona's] real name is Horowitz. And I said, 'You know, I'm thinking Winona Ryder sounds cool,' and she was like, 'Yeah!'"

8. Josh Hutcherson & Vanessa Hudgens

Following her split from hunk Zac Efron, Vanessa briefly dated The Hunger Games star Josh Hutcherson.

10. Claire Danes & Matt Damon

They dated while shooting their 1997 movie, The Rainmakers.

11. Justin Timberlake & Fergie

Before he famously donned double-denim and got it on with Britney Spears, Justin actually dated Fergie! At the time he was just 16 years old and the Black Eyed Peas front woman was 7 years his senior. Whoa.

12. Nicholas Cage & Sarah Jessica Parker

Just like Carrie from Sex & the City, SJP has dated her fair share of men over the years. Including Nicolas Cage in the early '90s, it would seem.

13. Courtney Cox & Michael Keaton

Our very own Monica from Friends dated the original Batman for a whopping 6 years! And after their broke up for unknown reasons, Courtney graciously only had nice things to say about her ex:

"It's the most important relationship I've ever had, and I think he's the most wonderful person I've ever met."

14. Kate Bosworth & Ian Somerhalder

Back in 2002, these two became an item after starring together in Rules of Attraction. Unfortunately, they only lasted a couple of months before going their separate ways.

15. Rosario Dawson & Jay Z

Before Jay Z became one half of the music industry's royal pairing, he actually dated actress Rosario Dawson back in 2000.


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