#32: Ro, Ro, Romo Your Boat
Jessica Simpson dated former football player Tony Romo for about a year and a half. Although their relationship was short-lived, it was not short on opulent, extravagant gifts. Jessica reportedly gifted Tony a custom-made speedboat that cost a whopping $100,000. The motorboat was a gift for his birthday, and Jessica surprised him with it during a party at their house.
![](https://moneytreestudio.com/wp-content/uploads/2023/02/33-1024x1024.jpg)
Some gossip columns speculated that Jessica was hoping the expensive gift would lead to a marriage proposal, but who knows if that’s true. What did happen, however, probably wasn’t what she hoped for. The couple broke up a few months later, right before her birthday! It’s reported that Tony kept the boat after their break up. We wonder if he still uses it…