There’s always love and trust early in a relationship. Why not? There’s no reason not to believe that you’ll be with your “soulmate” forever. If you’re going to be with the person you’re meant to be with, why bother signing a prenuptial agreement, right? Well, at some point the shiny veneer of marriage wears off and one half of the couple does something thoughtless which usually throws the marriage into chaos.
There’s the expected separation followed by the inevitable divorce. It’s at this point that all hell breaks loose. The once loving, now spurned spouse is out for vengeance after coming to terms with the rejection and wants what they’re due. Don’t get me wrong, some former couples handle things well and choose to “consciously uncouple” while others deal with the pain by attacking their philandering ex-spouse by hitting them where it hurts. That’s right, in their pockets.
Folks that have to ante up because of their mistakes are no doubt kicking themselves for not signing something before walking down the aisle (and probably for screwing up big time). Then there are those who were making far less than their new spouse when they get married and don’t see the point of signing a prenuptial agreement. However, many folks in this category have gone on to reach new heights in their careers and side businesses and have become the new bread winner of their family. When the marriage unfortunately ends, they’re the ones left wishing they’d put something on paper.
Here are 10 couples who left puppy love behind and seriously regretted not signing a prenup.
10 Gwen Stefani and Gavin Rossdale
After 13 years and three kids together, Stefani filed for divorce in 2015. They reportedly didn't sign a prenup and Rosedale was asking for half of her $120 million fortune. Keep in mind, despite a successful music career, Rossdale is worth less in comparison and has approximately $20 million in the bank. With his alleged cheating hyped as the reason for their divorce, Stefani wasn’t going to go down without a fight. They’ve supposedly recently agreed to a settlement that benefits both of them (still, Stefani can't be happy that she has to pay anything at all considering the circumstances). In happier times Rossdale had agreed that if things went sour, he wouldn’t go after her money. She’s no doubt (no pun intended) kicking herself for buying into that and wishes she could go back and change a thing or two.
9 Johnny Depp and Amber Heard
While not technically divorced yet, this couple chose to forgo signing a prenuptial agreement. Johnny is worth over $400 million (insert jaw drop) while Heard is worth an estimated $4.5 to $9 million. During settlement negotiations, California law usually just divvies up earnings and the spouse who earns the least walks away with a small fortune. However, they were only married for 15 short months so the verdict’s still out on just how big a slice of Depp’s mega million-dollar pie Heard will walk away with. If her claims of abuse are confirmed, that might play a role in her settlement.
8 Roseanne Barr and Tom Arnold
Back in 1990, Barr very famously got upset with her lawyer for simply suggesting she have Arnold sign a prenuptial agreement. She ultimately chose love and trust over signing a piece of paper and fired her lawyer shortly afterward. However, four years after they became husband and wife, Arnold and Barr’s martial bliss came to a screeching halt. Their divorce became one of Hollywood’s ugliest at the time, plenty of unpleasant accusations flew between the two and there was even a restraining order issued. When the dust finally settled, Barr lost $50 million which Arnold used to get himself back on the right track. He didn’t walk away from the marriage completely untouched though. Barr may have regretted not signing a prenup but Arnold must have regretted getting a large tattoo of Barr’s face on his chest.
7 Jessica Simpson and Nick Lachey
When these two love birds got married, Lachey was earning more money than Simpson was. His wealth at the time was thanks mostly to his time spent in boy band heaven as part of 98 Degrees. While Simpson was famous and wealthy in her own right, she chose to forgo signing a prenup. During their marriage, she launched her retail empire and became worth considerably more than Lachey. When their marriage ended in 2005 Simpson offered Lachey $1.5 million to walk away. He said “no way” to the offer and ended up with $10 million instead. Simpson stated many times recently that not insisting on signing a prenup was one of her biggest money mistakes.
6 Reese Witherspoon & Ryan Phillippe
Much like Jessica Simpson, Witherspoon was earning considerably less than her movie star husband when they married in 1999. At the time she’d only starred in films such as Cruel Intentions and Election. But the release of Legally Blonde gave her access to better roles and her career skyrocketed. She began earning $20 million per movie while Ryan’s star began to fade. In comparison to Witherspoon, he was earning a very small fraction of that per film. With no prenup in place, Phillipe was entitled to half of her fortune. Surprisingly, when Witherspoon married Jim Toth in 2011 she again chose not to sign a prenup. Granted, Toth is a talent agent worth $8 million but let’s hope for the best for these two since Witherspoon is now worth an estimated $80 million.
5 Mel Gibson and Robyn Denise Moore Gibson
This pair was married long before Gibson’s career took off. Their marriage lasted an amazing 28 years, a milestone compared to many celeb marriages. Marital bliss officially ended for these two in 2011. Since they didn’t sign a prenup when they got married in 1980, California law entitled Moore Gibson to half of Gibson’s tremendous wealth, $900 million to be exact. Details of their final settlement haven’t been made public but $450 million ain’t half bad when you’re starting life anew.
4 Paul McCartney and Heather Mills
Before marrying Mills, McCartney rejected the idea of signing a prenup even though friends and family urged him to do so. His repayment for being so trusting? An absolutely horrible divorce that has gone down in the Hollywood history books as one of the nastiest ever. Mills walked away with $35 million and McCartney has to pay for their daughter Beatrice's education, etc. until she’s 18. These expenses tally up to about $70,000 annually.
McCartney again threw caution to the wind when he walked down the aisle for a third time, this time with businesswoman Nancy Shevell. This time around his wife is bringing her own wealth to the marital table (she’s Vice President of Administration for New England Motor Freight – a transport company) so here’s hoping they make it the distance.
3 The Dream and Christina Milian
When these two started dating in 2009 it caught everyone by surprise. Even more so when they got married later that same year. Two years and a daughter later, they finalized their divorce. Christina has been in the music game for a while so she is undoubtedly a self-made millionaire. However, when their marriage ended, she managed to walk away with $4 million from her former beau plus $5,000 a month in child support payments. They’ve both moved on, and hopefully they’ve both learned a thing or two from their time together.
2 Ashton Kutcher and Demi Moore
This pair surprised everyone not only when they began dating but also when they eventually got married in 2005. Their marriage lasted six years before Kutcher’s cheating led to its demise. During their time together he went on to star in the hit series Two and a Half Men while Moore’s super stardom from the 80s and 90s had faded. Without a signed prenup to fall back on, their settlement battle raged on for two years before they finalized it in 2013. Moore is worth $150 million but was still able to wrangle spousal support from Kutcher. The final amount hasn’t been made public but Kutcher ended up paying more than he expected to just to close this chapter and move on.
1 Lamar Odom and Khloe Kardashian
These two love birds tied the knot in 2009 after a whirlwind romance that lasted only four months. Technically, they didn’t sign a prenup when they got married but instead came to their senses and signed one shortly afterwards. As an LA Laker at the time, Odom was no doubt the bread winner of the two. However, it’s possible that chronic drug use and drinking have depleted some of his wealth. Kardashian recently filed for divorce for a second time and stands to walk away with over $2.5 million once the dust settles. This settlement includes some pretty lavish things such as a new car at the end of each lease term, court side seats to LA Lakers games as well as a very substantial beauty and shopping budget. Not bad.