What do Reese Witherspoon, Britney Spears and Jessica Simpson all have in common? They are all women who were in incredible Hollywood relationships that were destined to last but somehow ended up failing. It seems utterly impossible to maintain a healthy relationship in Hollywood but we really thought these couples had something different going for them. From Brit and Justin Timberlake to Reese and Ryan Philippe to Jessica Simpson and Nick Lachey we all had faith that these couples would surpass the cliche of celebrity breakups. Unfortunately, none of them did and all three relationships ended up in emotional turmoil.

Let's take a look at these three heartbreaking Hollywood stories to see if there's any hope of reconciliation.

Britney Spears and Justin Timberlake

Britney Spears and Justin Timberlake were definitely Hollywood's 'it couple' back in the early 2000's. The pair dated for just over 4 years before breaking up amidst rumors of a cheating Britney. Since then, they have both dated and have both had some somewhat serious relationships (Brit was married to Kevin Federline and Justin was in a long-term relationship with actress Cameron Diaz) but both ended up heartbroken and alone. What does this mean for us? A reconciliation isn't completely out of the question. The former couple is back on talking terms and rumors have even sparked that the two might be recording a duet together.

Possible Reconciliation Rating - 8/10

Reese Witherspoon and Ryan Philippe

Reese Witherspoon and Ryan Philippe met at Reese's 21st birthday party. After dating for a short time, the two decided to get married and start having children. They ended up having two children, Ava and Deacon, and lived a fairytale life. Unfortunately, like most of the relationships in Hollywood, the fairytale was short-lived. Not long ago, Reese and Ryan announced they were separating amidst rumors that Ryan was having an affair with Abbie Cornish, his co-star in an upcoming movie they were filming. The two remain on speaking terms for the sake of their children but do not communicate as anything but parents to their children. There is no friendship and definitely no relationship between the former couple.

Possible Reconciliation Rating - 6/10

Jessica Simpson and Nick Lachey

After filming "Newlyweds: Nick and Jessica", Nick Lachey and Jessica Simpson quickly became Hollywood's hottest couple. Jess' ditzy ways combined with Nick's compassionate (yet humorous) personality made for one heck of a tv show. From watching the 3 seasons of the Newlyweds, it seemed clear that Nick and Jess were in it for the long haul. But, again, after several rumors of cheating, the fairytale romance came to a crashing halt. Now, almost a year after the divorce, both Nick and Jess are in long-term relationships and neither have made any effort towards reconciliation. Vanessa Minnillo, Nick's girlfriend, recently moved in with the former 98 Degrees member while Jess is off dating musician John Mayer. The odds of a reconciliation between this couple is (sadly) not looking good.

Possible Reconciliation Rating - 3.5/10