Dane Cook & Kelsi Taylor – 27 Years

You may think that Beyonce and Jay-Z were weird by dating when he was in his thirties, and she wasn’t even in her 20s yet. But comedian Dane Cook actually had to wait for his wife Kelsi Taylor to turn 18 before they could start dating each other.

He even joked on Jimmy Kimmel Live! that she wasn’t even alive for most of his life. But they knew they wanted to be together since they met at a game night Cook was attending at a friend’s house. Cook probably figured that if anyone thought it was weird, like a good comedian, he would just joke his way out of trouble.