Marriage is definitely a very rewarding experience. However, that isn’t to say that marriage is always easy. After all, the path of true love never did run smooth.

When you’re a rich and famous person tying the knot, the additional wealth and notoriety can make for additional concerns about partnering up. No one wants to lose all of their assets should they get divorced.

Thankfully, that’s why prenuptial agreements exist! These legal documents protect both parties in the event of a divorce. That said, the strange clauses in these 14 celebrity prenups prove just how tough marriage can really be.

1. Mark Zuckerberg and Priscilla Chan: The Facebook founder and pediatrician is valued at $74.6 billion, so it’s no wonder they signed a prenup. In it, Zuckerberg agreed to take Chan out on a date once a week and promised her 100 minutes of alone time a week outside the office or the home.

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2. Jessica Biel and Justin Timberlake: Valued at $248 million, this all-star couple is taking no chances! When they signed their prenup, they made sure to add a clause that immediately gives Biel $500,000 if Timberlake ever cheats on her!

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3. Nicole Kidman and Keith Urban: These celebrity Aussies are worth $205 million, and Kidman’s prenuptial agreement aimed to protect them both. Since Urban struggled with alcohol and cocaine addiction, he is entitled to $600,000 for every year they are together—provided he remains sober.

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4. Jay-Z and Beyoncé: This powerhouse duo is worth $1.6 billion. Beyonce is entitled to $5 million for every kid they have together. The prenup also says that she gets $10 million if the marriage ends before two years and $1 million a year for every year they remained married up to 15 years.

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5. Kim Kardashian and Kanye West: What’s weird about this couple’s prenup is that there is no clause about child custody! However, there is a clause saying that Kardashian’s mother, Kris Jenner, can’t make career decisions that affect the couple.

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6. Brad Pitt and Angelina Jolie: Although Brad Pitt and Angelina Jolie are now divorced, everyone knows that Pitt didn’t cheat. How? Because in their prenup, Jolie would’ve received sole custody of the kids if that happened.

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7. Michael Douglas and Catherine Zeta-Jones: If they were ever to divorce, Zeta-Jones would receive $2.8 million a year from her ex. Should they divorce because he cheated, she would get a $5 million bonus!

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8. Tiger Woods and Elin Nordegren: Too bad Woods cheated! If he hadn’t, Nordegren would’ve taken home a mere $20 million, but the cheating bumped that amount up to $110 million. Woods really wanted her back, so much so that he offered a $200 million prenup. She declined.

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9. Lamar Odom and Khloe Kardashian: When their marriage ended, Kardashian made sure she didn’t walk away empty-handed. She took home $2 million for the four years they were married. She also receives courtside Lakers seats, a new car every time her lease is up, and she got the house in the split, too!

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10. Jessica Simpson and Tony Romo: This couple never got married, and a certain clause in their prenup might indicate why. Romo had the nerve to ask Simpson to pay him $500,000 for every pound she gained over 135.

11. Tom Cruise and Katie Holmes: When Cruise and Holmes split, Holmes took home $3 million for every year of their marriage. She also gets an allowance of $400,00 for the care and upkeep of the couple’s daughter, Suri.

12. Britney Spears and Kevin Federline: This couple’s prenup was pretty special because the document alleged that the couple had never “technically” been legally married. To that end, Federline got just $1 million when they split.

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13. Denise Richards and Charlie Sheen: This couple’s prenup included a clause that awarded her $4 million if Sheen was ever caught cheating. Interestingly (but not surprisingly), this wasn’t the first time Sheen had a cheating clause in one of his prenups.

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14. Liz Taylor and Larry Fortensky: Taylor was an old hat at marriage by the time she wed Fortensky. Rather than agree to paying him when they got divorced, Taylor agreed to pay him if they managed to stay married for five years!

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Who knew that love could be so unromantic? Good thing these celebrity couples protected themselves the way they did.

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