10 Most Awkward Real Life Relationships In Wrestling History

2. Shawn Michaels & Bret Hart & Sunny

The issues between Shawn Michaels and Bret Hart in the mid-1990's were bad enough as it was, but when Michaels referenced Bret having "Sunny Days" in a promo on television, almost in a throwaway line, things were taken to a new level. The line discussed the rumours that Bret was cheating on his wife and having an affair with Sunny. Bret's wife, and the rest of his family, heard about the rumours, and Bret says there was plenty of tension, including his children asking him if he was really doing it. Bret has continuously denied the rumours, but now that the line was out there in the open, certain things were awkward. Bret felt Shawn was an immature, disrespectful punk. The best part about the rumours were that Sunny and Shawn pretty clearly had something going on when you would watch them on television together. Years later, in a shoot interview, Sunny would admit that she slept with Michaels, but she also said that she never, ever did anything with Bret, putting the entire thing to rest. You probably couldn't have Bret and Shawn together backstage without some sort of an argument breaking out back then. After Sunny was brought into the mix, especially because she was friends with both men, things had to have been even more awkward for everyone involved. Sunny couldn't be seen talking to Bret too much, or people would start gossiping. She couldn't be seen with Shawn too much, or people would start gossiping. There are a lot of "damned if you do, damned if you don't" scenarios in wrestling, but that ranks right up there with the best/worst of them.
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Columnist/Podcaster/Director at LordsOfPain.net for nearly seven years, with nearly 2000 total columns written. Interviewed and/or involved in interviewing the likes of Tyler Black/Seth Rollins (twice), Diamond Dallas Page, Jimmy Jacobs, Christopher Daniels, Uhaa Nation and more.