10 Most Awkward Real Life Relationships In Wrestling History

4. Triple H & Stephanie McMahon & Chyna

In a situation somewhat similar to the Benoit/Sullivan/Woman scenario, Triple H, Stephanie McMahon, and Chyna were involved in the biggest love triangle in wrestling history, based on the consequences and repercussions of what happened. At one time, Triple H was merely an on-the-rise worker dating Chyna, who also happened to be his bodyguard, of sorts, on television as a part of Degeneration X. He was clearly destined for big things with the company, especially after he withstood punishment from management after the Madison Square Garden "Curtain Call" incident without complaining. The company saw enough in him that they were going to pair him with Stephanie McMahon for a storyline. That storyline, as you know, saw Triple H take a "drugged" Stephanie to a drive-up wedding chapel and secretly marry her before she was set to marry Test, only for Steph to turn heel and reveal she was in on it the entire time. This would put in motion one of the bigger "power couples" in wrestling history. Somewhere along the way, though, while acting like a fake couple, they began having real feelings for each other. All of the travel they were doing together, and all of the time they spent going over the storyline, helped them reveal they were actually falling for each other. Triple H had gone from dating Chyna to dating the daughter of the company's owner, which, even if you're not talking about looks, is quite the tremendous upgrade. It took him from dating someone who was an employee to dating someone that was next-in-line to run the entire company. It used to be the "in" thing to say that he only got with Stephanie to further his place in the company, but at this point, if you can't look at them and see that they're still madly in love with each other, you're not paying attention. All the while, Chyna had to sit back and watch it all happen. With the daughter of the owner involved, it's not like she could march into Stephanie's dressing room and beat the hell out of her, if she knew what was best for her career. That had to be brutal for her. Chyna would go on to get released from her contract, and have her life spiral into addiction and the porn business. Triple H would have his career elevated, in and out of the ring, and is now Executive Vice President for the entire company. Stephanie McMahon would settle down, have a family, and become the woman we all know (and some of us love) to this day. Everyone's lives changed because of this one.