Over the years, there have been several romantic relationships within WWE (both on and off camera) that have captured the attention of audiences around the world. However, if there was one relationship that captivated us the most and has the most intriguing backstory of them all, it's the relationship between Stephanie McMahon and Triple H. What started off as a storyline angle quickly transitioned into an actual full-blown relationship. As many of us know by now, it all started in the fall of 1999 when Triple H drugged Stephanie McMahon into a Las Vegas wedding (more on that later) and Stephanie found herself attached to Triple H against her will. Later on, at Armageddon 1999, Stephanie turned heel for the first time in her career by helping The Game defeat her father, Vince, revealing that she had been in on Trips' planned takeover of WWE all along and that her naivety had been all a ruse. For almost two years onwards, the two were WWE's resident power couple as the McMahon-Helmsley era would reign supreme over the company. Then, strangely enough, art would start to imitate life. Behind the scenes, a genuine relationship started to blossom between the two the more that Triple H flirted with the youngest McMahon prodigy backstage. As both have insisted in interviews, Trips made advances towards Steph, Steph resisted for as long as she could before giving in, and now they're actually married with children. Not only that, but both have inherited some powerful backstage roles and are both heirs to the company. If not for the awkward moments in between, both on and off camera, this would make for the ideal Hollywood romance.
However, as in all relationships, both parties have to keep up a certain public image to avoid one making the other look bad. Or doing something stupid enough to make both parties look bad. In their case, both Stephanie and Triple H have surely made each other grimace throughout the years -- both as characters and as business partners -- but for now, we're going to focus on Triple H. Whether it be intentional or otherwise, Triple H has done/said things on and off screen that have essentially made The Billion Dollar Princess look bad in the public eye. And due to his high position within the company and the brownie points he's acquired from the McMahon family, he hasn't received any punishment apart from probably a side eye from the Mrs. at the family table at dinner. Still, that doesn't make any of these following moments any less embarrassing for Stephanie McMahon.
12 Refusing to Sign Annulment Papers
After Triple H had revealed the previous week that he had slipped a mickey in Stephanie McMahon's drink and had forced her into a Las Vegas drive-in wedding (more on that later), Stephanie brought annulment papers to Triple H's doorstep and demanded that he sign them. Triple H took the opportunity to, instead, make a mockery of Stephanie's orders and act like, as Stephanie called him, an "insincere son of a bitch." At the start of the segment, Triple H pretended to be genuine in praising Stephanie. He vouched for her being a decent woman and shed tears at the thought of ending their marital bliss. When Stephanie came out, he proceeded to crack subtle sex jokes and refused to sign the papers. Then, when Vince McMahon came onto the ramp to intervene, that's when Trips decided to force himself onto Steph for a big ole smooch. Safe to say that both of the McMahons present that night felt a little humiliated.
14. Destroying Her Car
In the midst of their on-screen divorce in 2002, Stephanie McMahon and Triple H battled over what belonged to whom and who had the right to have what, the former being intent on telling the latter that they should split their shares and property 50-50. In a unique way, Triple H obliged. On the March 7th episode of SmackDown, Stephanie walked to her car (which was an old Sweet-16th birthday gift) and found only half of it intact. Turns out, Triple H did a little bit of remodeling. Or, more appropriately, demolishing. As Stephanie wept and bemoaned her tarnished vehicle, he reminded her that he only wanted to split what they owned 50-50, just like she had asked. It was clear she hadn't expected The Game to have her precious car ripped in half.
13. Replacing Her Lotion
On the March 4th, 2002 episode of RAW, weeks after Triple H and Stephanie McMahon broke up in spectacular fashion during their wedding, Triple H tried to return some of his ex-wife's belongings to her in a box. One of these belongings happened to be Stephanie's beloved Pristine Mist lotion which she didn't hesitate to rub all over her body as soon as she received it from Triple H. Unbeknownst to her, The Cerebral Assassin had actually replaced her lotion with some sort of faux cream that gave her a terrible itching sensation and zits all over her body. Miraculously enough, her monstrous markings disappeared (or the makeup artist just forgot to touch her up before going out) later in the night just in time for Steph to make an appearance during Trips' Steel Cage match with Kurt Angle, but for that moment at least, Stephanie was outraged at what Triple H had done.
11 Killing Their Angle With Kurt Angle
Some of us may remember that during the summer of 2000, a storyline between Kurt Angle, Triple H, and Stephanie McMahon started to develop. At a point when the McMahon-Helmsley regime was still running wild over WWE, Steph and Angle developed a close friendship that slowly manifested into a short-lived affair of sorts when the two started developing feelings for each other. Then, shortly after Angle and Stephanie shared their first kiss, the entire angle was nixed without a big blow off -- not even a blow off match between Angle and Trips, though they did wrestle at Royal Rumble 2001, but not over Stephanie. Many wondered why the angle was cut so short, but fairly recently, Dave Meltzer of The Wrestling Observer revealed that Triple H had approached the creative team about nixing the angle because he didn't think it was realistic for Stephanie to leave him for a guy like Kurt Angle. Sounds like Trips was a bit jealous. Not many women like the jealous types, and if Stephanie falls under that category, then she certainly wasn't fond of Triple H nixing her big angle with Angle so soon just as it started to gather steam.
10 The Candice Michelle Segment
Though their real-life marriage was never acknowledged on WWE television until 2009 (around the time Randy Orton was feuding with the McMahon family), it was common knowledge among fans that Triple H and Stephanie McMahon had gotten hitched for real, which is why segments like these were awkward to watch. Around the time Triple H reunited with Shawn Michaels as part of DX, he had this outdoor segment with Candice Michelle that was littered with sexual innuendo. As the two conversed, both reached an odd climax, which was later revealed to be due to both parties receiving fellatio from women who were fondling them under the table at the same time. It was all in good fun, but it had to be strange for Stephanie McMahon to see her husband being fellated by another woman on TV.
9 The Katie Vick Angle
While Stephanie McMahon had no part in this segment on or off camera, it still couldn't have been easy to have been dating the guy who had humped a mannequin inside of a church casket on live TV. The Katie Vick segment remains perhaps the most infamous segment in WWE history, and the ludicrous nature of this one segment was lewd enough for the plug to be pulled on the whole angle shortly afterward. Stephanie had to have felt a little bit of second-hand embarrassment knowing everything Triple H had said and done during this segment. Imagine Stephanie running into someone who and being asked something along the line of "Aren't you the wife of the guy who had sex with a mannequin, which was supposed to be a dead body?" Should be safe to say that it wouldn't have been one of Stephanie's proudest moments.
8 Hooking Up With Steph While With Chyna
By bringing Stephanie McMahon under his wing as his mistress back when he was still dating Chyna in real life, Triple H put Stephanie in a very compromising position -- not just in terms of getting Stephanie's name forever associated with being a homewrecker, but also in terms of exposing Stephanie to tons of drama out of this triangle. It's a known fact that Triple H's affair with Stephanie left Chyna heartbroken and was one of the factors that led to Chyna losing her job with the company. Chyna never forgave Stephanie, and in numerous interviews, proclaimed her disappointment over the Billion Dollar Princess's actions. In many ways, Triple H unintentionally set Stephanie up for public embarrassment by interweaving her into this web of lies, deception, and heartbreak.
7 His (Alleged) Affair With Christy Hemme
Christy Hemme is most deeply associated with TNA Impact Wrestling after a 10-year stint with the company from 2006 until 2016. But before that, she had a short, yet noteworthy, run with the WWE. After winning the 2004 Divas Search, Hemme was pushed as one of the company's top Divas, so much so that it earned her a Playboy cover centerfold and a Women's Championship shot against Trish Stratus at Wrestlemania 21. Then, under unknown circumstances, she vanished from the company by the end of 2005. To this day, no one knows why the WWE would let go one of their top Divas under such short notice. But the big rumor that has been circulating for years is that she was fired after an alleged affair with Triple H. Apparently, the two got a little too cozy on the road together and things got steamy between them. When word got back to Vince and Stephanie McMahon, Hemme was abruptly drafted from Triple H's brand on RAW and over to SmackDown, where she was de-pushed and eventually released. If any of this is true, Stephanie had to have been embarrassed for obvious reasons, especially for the fact that Steph's whole relationship with Triple H was built on their own affair. Trips having an affair behind her back had to have felt like some bad taste of karma.
6 The Grand Canyon Insult
During their 2002 feud against each other, Stephanie McMahon and Triple H threw a good handful of verbal jabs against each other. Perhaps the biggest (and for Stephanie, the most embarrassing) came on the February 25th episode of RAW. It all started when Stephanie questioned Triple H's manhood by mentioning that he was always a little on the short side in the bedroom. Triple H quickly came out to the ramp to correct Stephanie. He told her that it wasn't that The Game was short, but that "the field [he] was playing on was too damn big" because "even a 747 looks small when you're flying it into the Grand Canyon." After that last one, Stephanie was left speechless, which is a rare thing to ever happen in her long career. To make things even harsher, Triple H then called her "The Great Wide Open."
6. The Pedigree At Mania
For months during their feud in 2002, it had been teased that Triple H would finally get his hands on Stephanie McMahon, but whenever he had the opportunity, she always found a way to somehow weasel her way out of his clutches. However, there was no weaseling away when she was in Chris Jericho's corner when he fought Triple H in the main event of WrestleMania X8. After interfering in the match one too many times, Triple H finally had enough and wound up getting his hands on The Billion Dollar Princess before the show was over. Jericho was nowhere in sight, and no one was coming out to save her this time. So Triple H grabbed her, set her up for a Pedigree, and then finally executed it, planting his ex-wife's face into the mat. For the first time, Triple H finally got revenge on Stephanie McMahon -- to her great embarrassment, of course.
5 Groping Her On TV
During the very beginnings of their relationship, Triple H was very flirtatious with Stephanie McMahon. As Stephanie herself explained in a 2003 interview with Howard Stern, Trips would drop clever hints of his attraction to Stephanie when they were behind the scenes. Those hints always kept Steph guessing in the back of her mind, but at the end of the day, she'd always convince herself that Triple H was just being a jokester or that these "hints" were just in her head. That was until an episode of WWE programming where Triple H copped a feel on her in front of a live audience. While Steph was around the ring and Triple H was on the ground, he crawled around Stephanie, and in a subtle moment of breaking character, he groped her leg. This may not have gotten picked up by the cameras, but this was the first moment that Stephanie McMahon realized that Triple H was actually legitimately flirting with her. The gesture made Stephanie blush.
4 Their On-Screen Wedding
On February 11th, 2002, for the second time in his career, Triple H ruined Stephanie McMahon's wedding. This time, he was supposed to be the groom. Shortly after returning from his career-threatening injury, Triple H decided to renew his vows with Stephanie McMahon after she told him that she was pregnant. But right before the ceremony, Triple H got tipped off by Linda McMahon that Stephanie had lied about her pregnancy to keep him around. So during the wedding, he called her out on being a "no good lying bitch." He tarnished the ceremony by harshly berating Steph, knocking out her father with a punch and a Pedigree, demolishing the decorations, and pie-facing Stephanie right before throwing his wedding ring at her.
3 Causing Her Wardrobe Malfunction
Most of us know about this moment by now. It's been talked about to death, which has likely only added to the embarrassment which Stephanie probably still feels to this day. In the midst of their feud heading into Wrestlemania X8, the King of Kings attempted to Pedigree the Queen of Queens through an announcer's table, and in the heat of the moment, her breast popped out of her dress for the world to see on national television. This wasn't the first time that Stephanie had a wardrobe malfunction on TV. Nor was it the last. But it's definitely the most talked about.
2 The Las Vegas Wedding
Ah, the moment that started it all. Seems like only yesterday that Triple H ruined Stephanie McMahon's wedding to Test by revealing that he had drugged Stephanie earlier and had taken her unconscious body through a Las Vegas drive-in ceremony where the two were wed. Not exactly a typical Disney-esque romance, but it led to the real-life nuptials of Steph and Trips, although the circumstances surrounding their on-screen marriage still come off as fairly shady by today's standards. Or, better yet, just thoroughly messed up in retrospect. Triple H roofied Stephanie McMahon, dragged her to Las Vegas, took her through a 24-hour drive-in wedding chapel, mimicked her voice for the "I do," and to top it all off with a cherry, Triple H admitted to sexually assaulting her in her sleep. Or, as he put it, he and Steph did "consummate the marriage" several times while she was incapacitated. Saying that Stephanie was embarrassed on her wedding day would be an understatement in this case.
1 Orchestrating a Fake R--e Scene
As a heel during the Attitude Era, Triple H did some pretty dastardly things to ensure he would retain his WWE Championship. One of the most dastardly has to be when he orchestrated an elaborate sexual assault against Stephanie McMahon to distract his opponents. On the November 8th, 1999 episode of RAW, Triple H defended his title against Test, who was moments away from winning the belt from The Game. Just as Test was seconds away from a pinfall victory, Road Dogg appeared on the Titantron to announce that Stephanie McMahon was having the time of her life backstage. He then brought the camera to a dressing room and opened the door to reveal Billy Gunn and X-Pac assaulting a woman who appeared to be Stephanie. The appalling scene distracted Test (along with Shane and Vince McMahon) long enough to allow Trips the opportunity to retain. It was later revealed that this was all just a cleverly orchestrated ploy setup by Triple H to secure the winning edge. Though DX never denied assaulting a woman backstage, they did confirm it wasn't Stephanie. And even if we look past the veil of kayfabe, both Stephanie and Triple H have to feel a little embarrassed about taking part in such a crass segment.