#1 The Undertaker and Michelle McCool – 15 years
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We are closing this list off with the wrestler who has made kayfabe a part of his life, The Undertaker. Taker is one most the most iconic figures to step into the squared circle but he showed that even someone as legendary as The Deadman has a heart, with his relationship and eventual marriage to Michelle McCool.
The two met during their run together in the WWE where McCool had some amount of success. This didn’t deter The Phenom, though, as he got together with the former school teacher following his second divorce.
There is a staggering fifteen-year gap between the two but that has hardly seemed to matter as they have been together for a long time now and even have a daughter to celebrate a relationship that has seen a softer side of The Undertaker we rarely if ever, get to see.
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