10 Most Awkward Real Life Relationships In Wrestling History

5. Chris Benoit & Kevin Sullivan & Woman

Let's go ahead and skip beyond the initial discussion about the final weekend of Chris Benoit's life and how it ended. Everyone wants to bring it up when his name is mentioned, and for good reason, but this is a different discussion altogether. Sullivan, as booker for WCW, was coming up with different storylines for the company. One of those storylines featured his feud with Benoit. At the time, not only was Sullivan managed by Woman, he was married to her in real life, as well. Sullivan delivered the idea of Woman turning on him and joining up with Benoit. Sullivan, ever the old school guy, suggested Benoit and Woman travel together to make it look more real. He said they should stay in hotels together, go out to eat together, hold hands in public, and do everything else that would make people think Woman had actually left Sullivan for Benoit. This was 1997, when wrestling fans were smarter to the business than they were decades earlier, so Sullivan really wanted to go over-the-top to make fans believe. Art imitated life yet again, as Woman and Benoit traveling together helped them to begin falling for one another, and she would actually leave Sullivan in real life for Benoit. Again, this was in the middle of Benoit and Sullivan feuding with each other on television. If you're Kevin Sullivan, how do you feel? Of course, you're mad at them for what they did to you, but at the same time, he all but gave them permission to do it by telling them to spend all their time together. It added a new layer to their feud, which was very hard-hitting and intense as it is. On his WWE DVD documentary, Benoit would say that he gained a new level of respect for Sullivan during their feud. He said that Sullivan had every right to turn their matches into something of a "shoot", but that he never did, and he never took any liberties in his offense. To this day, people are still unsure how the man known as "The Taskmaster" was able to do it, but he did.