Celebrity Families Who’ve Dated One Another’s Exes: Wayans, Kardashians, Bidens and More

Celebrities dating each other’s friends isn’t something new, but dating a family member’s ex is a bit more uncommon — and definitely more taboo.

Damon Wayans Sr. confirmed in April 2025 that in the early 2000s he dated his nephew’s ex-girlfriend after falling “in love.”

Kourtney Kardashian, meanwhile, had a fling with Justin Bieber in 2015 after he was rumored to have dated her younger sister Kendall Jenner. Kourtney’s husband, Travis…