#2. WWE EVP Triple H
A year after joining WWE in 1995, Triple H started dating Chyna. Their relationship lasted nearly four years. However, The Game and The Ninth Wonder of the World split in 2000. That same year, he started dating Vince McMahon's daughter, Stephanie.
At the time, Stephanie's brother, Shane, was also on the roster. A few years ago, Bruce Prichard spoke about Shane's reaction to his sister dating The King of Kings:
"I don’t think Shane was happy and that’s me putting words in Shane’s mouth, but I don’t think Shane was happy at all. I think that Shane is very protective of Stephanie, very protective of his mother and if I were a betting man back then, I’d bet Shane wasn’t in favor of it, but he’s also not one of those guys who’s gonna go talk about it either," he said on the Something to Wrestle podcast.
Triple H and Stephanie dated for nearly three years before tying the knot in 2003. They now have three daughters.
The former WWE Champion and his brother-in-law have shared the ring several times over the past two decades. Nevertheless, they only squared off once in a singles bout, in which The Game came out with the victory.