13. Brody Jenner & Josie Canseco
Jenner’s whirlwind romance with 22-year-old model Canseco is over. TMZ first reported the news that the pair had split after three months of dating. Jenner, 36, met Canseco through his The Hills: New Beginnings costar Frankie Delgado, and began dating two weeks after he announced his split from wife Kaitlynn Carter in August. While their romance was short-lived, she received Jenner’s mother, Linda Thompson’s approval. “I’ve met her several times and she’s a darling girl,” said Thompson. “So you know, life moves on.”