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#3. WWE Chairman Vince McMahon and Candice Michelle - 33 years
WWE Chairman Vince McMahon has been involved in some interesting romantic storylines throughout his career. In real life, he's married to Linda McMahon, but "The Boss" didn't let that stop him from portraying a playboy on WWE programming.
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Candice Michelle came to WWE following the 2004 Raw Diva Search. She was part of a trio with Torrie Wilson and Victoria, and the three women were known as Vince's Devils.
Look who just shut down all of Tony Khan's critics! More HERE.
During this time, Michelle was part of a romantic storyline with the WWE Chairman, where she was able to seduce him into giving her what she wanted.
Michelle was just 27 years old at the time while the WWE Chairman was 60 years old. So the age gap between the two stars, who were seen locking lips several times on WWE programing, was a shocking 33 years.
Michelle went on to be taken seriously as a wrestler. Later in her career, she became the first former Diva Search contestant to win the WWE Women's Championship. Pro Wrestling Illustrated even named her the Woman of the Year in 2007.
