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#4. WWE Chairman Vince McMahon and Torrie Wilson - 30 years
WWE Chairman Vince McMahon has been in several romantic storylines with female wrestlers over the years. The most famous example was his storyline affair with former WWE Women's Champion Trish Stratus. One of his most memorable romances came in 2001 when Torrie Wilson made her way to WWE. Shortly after her departure from WCW, she became The Chairman's latest affair.
This relationship didn't last very long, as Wilson later stepped into a romantic storyline with Tajiri. But at the time, Wilson was just 25 years old, and she was learning the ropes in the wrestling business. The future WWE Hall of Famer was seen as a valet in WCW, but she was finally learning to wrestle in WWE.
Vince McMahon had already made a name for himself as the Chairman of the company, and he had quite a reputation with female wrestlers at that time. At 55, McMahon was shockingly 30 years older than Wilson when the two stars were paired up in this storyline. Of course, McMahon was part of several romantic angles in the years that followed.
