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11. Paris Hilton
We have to admit that we struggle to consider any relationship that Paris Hilton gets into as a particularly serious one. Perhaps we are being too cynical and negative, but that is just how we feel. And despite still being quite young herself, Paris managed to find her way onto our list.
In 2012, when she was 31, Paris started dating River Viiperi, a Spanish model who was only 21 at the time. Even if you are really bad at math, you probably figured out that she is 10 years his senior. While they were dating, she said she didn’t even notice the difference since she saw herself as perpetually 21-years-old.
In 2014, the couple broke up and soon enough, rumors started spreading that she replaced River with a younger model (in both senses of the word) Jordan Barrett who was barely legal at the time.