#22: Dane Cook and Kelsi Taylor
There are some celebrities out there that even though they have a significant age gap, do not seem to let that get in the way of their romantic connection. To be honest, we’re not even sure how these couples begin dating in the first place… Like how do two people, of such different ages even find themselves in the same social setting?

But once-popular comedian, Dane Cook has found himself in a relationship with 23-year-old singer and model, Kelsi Taylor. The couple has been together a few years now, which is somewhat surprising considering they share an age difference of 26 years. We’re not entirely sure what someone so young sees in someone so much older than her, but hey, love knows no bounds.