Jessica Simpson and Tony Romo This is a story of a couple who never married, which is for the best given their prenup negotiations. More than a decade ago, singer and actress Jessica Simpson dated Dallas Cowboys quarterback Tony Romo. Throughout their relationship, Simpson was scrutinized.

Jessica Simpson and Tony Romo - 'Porker Clause' In their martial prenup, Tony created a clause that fans joking refer to as the "porker clause" stating that if Jessica gained over 135 pounds during their marriage that Romo would receive $500,000 for every extra pound.

Tony Romo famously dated stars such as Carrie Underwood and Jessica Simpson before finding The One in Candice Crawford. Romo and Crawford were first romantically connected in 2009, the same year that Romo and Simpson called it quits after nearly two years of dating.