On-again off-again-on-again couple we never understood John Mayer and Jessica Simpson is off again. And the couple we totally thought would last Kate Hudson and Owen Wilson are off again. Larry and Laurie David have announced their separation after 14 years of marriage . All this breaking up has us feeling a bit nostalgic for celebrity couples of the past. the ones that got away. Let’s reminisce, shall we?

Wow, blast from the past! Married in 1991 Richard Gere and Cindy Crawford split just four years later. Many speculated that their eighteen year age difference was to blame. That dress is so 1992!

Are we the only ones who thought Julia Roberts and Benjamin Bratt would get married and have kids together? Not to be, at least not with each other. They made a cute couple.

Cameron Diaz and Matt Dillon split after three years together, according to Dillon, Diaz wasn’t ready to settle down. Hm. She’s just not that into you.

Madonna and Sean Penn split after a tumultuous 3-year marriage and in doing so, put an end to their rocky relationship with the paparazzi.

Click Read On to see more celebrity couples from the past and tell us who you think should get back together

Ok, most bizzareHollywood couple ever. Wonder if she ever listens to “Dear Ben”. It was embarassing to listen to even when they were together. He looks like Arm Candy in this photo. Jen has the Mars Attacks hair.

Ben and Gwyn. He’s big on that rhyming thing. Their post Brad-Gwyn relationship was the subject of much are they or aren’t they speculation. In fact personal photos of the couple together are rather difficult to come by.

The. Golden. Couple. Seriously never thought this would end and still totally want them to get back together. It’s a sickness.

Brad Pitt and Gwenyth Paltrow. The pre-golden couple. He’s such a morpher.

Truly didn’t see this breakup coming. A normal non-celeb guy seemed perfect for Sharon. So love this dress!!

They never had a chance with the reality show life style from day one of their marriage. Reunion? We’re not ruling it out. And we don’t think Jess has either.

The break up of Tom and Nicole seriously came out of nowhere. Let’s blame Penelope and her terminal hotness.

Oops he did it again. Cruz and Cruise. Actually they were pretty hot together. We love her.

Least surprising breakup ever. Twenty years her senior , the marriage between Angelina Jolie came in surprisingly long at three years. They split two months after Maddox was adopted, citing irreconcilable differences. Post divorce, Billy Bob Thornton famously and rather rudely unloaded to Esquire magazine “Sex doesn’t have to be with a model to be good. Sometimes with the model, the actress or the ’sexiest person in the world’, it may literally be like fucking a couch.” Nice.

After eleven years of marriage and four children, Bruce and Demi split, amid rumors of infidelity. One of the saddest celeb breakups ever.

Pre-Demi, Ashton referred to Brittney Murphy as “his first wife”. Their intense romance began while shooting the atrocious Just Married.

First of all, who cheats on Uma Thurman? And secondly did this guy ever shower even once during their entire marriage?

Ryan Phillipe and Reese Witherspoon. This one came out of nowhere. We live for her. Hopefully the Jake Gyllenhaal thing will work out.

Ah, young love. Britney and Justin. They really were cute together.

Paris Squared. Paris and Paris. Hilton and Latsis. What pushed his parents over the edge, the sex tape or the Carl’s Jr commercial. Hmm.

Tell us in the comments who you want to see in volume II

Who should get back together? This is officially the our most ridiculously high schoolesque post ever. Having fun?

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