Randy Orton, widely known for his commanding presence, experienced a notably uncomfortable moment when he had to kiss Stephanie McMahon during a WWE storyline, all while her father, Vince McMahon, watched. This act occurred during a segment that highlighted intense tension and conflict among WWE’s top figures and contributed significantly to Orton’s character development.
Back in the late 2000s, Orton was climbing the ranks rapidly. Young and driven, he was eager to prove himself and didn’t hesitate to engage in controversial storylines, including a heated feud involving the McMahon family. During an episode of Monday Night RAW, Orton not only attacked Stephanie McMahon but also sealed the scene by kissing her directly in front of her husband, Triple H, amplifying the drama.
Behind-the-Scenes Preparation for Orton’s WWE Kiss Segment
In a recent conversation on the WWE series What’s Your Story, Randy Orton and Stephanie McMahon recounted what it took to execute the infamous kiss. Vince McMahon, who was closely involved in the creative direction, meticulously supervised the rehearsals to ensure every detail was perfect. He insisted on seeing the full sequence, from Orton delivering a DDT to Stephanie while Triple H was restrained on the ropes, to the exact moment of the kiss.

Vince’s involvement was hands-on, questioning how Orton would perform the kiss right in front of both Stephanie and Triple H during rehearsals. Orton described the rehearsal efforts, explaining how Vince wanted to determine proper placement and timing to keep the segment believable and safe. This included managing the distance so Triple H could not interfere while restrained.
“So, the rehearsal, I don’t know if you remember, but Vince wanted to kind see where we were gonna be … H is handcuffed, how much distance … where the DDT needs to go down, so he can’t reach and all that [right, right] and then ofcourse like ‘how are you gonna’ [do the deal] and ya and I was like, like this.” —Randy Orton
Despite the rehearsals, Orton said he found performing the kiss extremely awkward and hoped it might be cut from the final show. Nevertheless, the moment aired as planned and turned into one of the most memorable points in his career, helping establish him as a compelling heel character.
“In the back of my head, not realising how cool of a moment it would eventually been, I’m thinking like god I hope time is cut … I don’t even want to say the K word … but ya super super … I was just like awkward so awkward.” —Randy Orton
While visibly uncomfortable during practice, Orton managed to deliver the segment seamlessly on live television. The scene generated significant crowd reaction and was a pivotal moment that propelled his villainous persona forward, cementing his legacy among WWE’s top performers.
Randy Orton’s Heated Feud Against the McMahon Family
The kiss was just one episode in Orton’s fierce rivalry with the McMahon family that dominated WWE storylines in 2008. This feud started with Orton confronting Vince McMahon directly, including moments where he slapped Vince and attacked Shane McMahon. His aggression towards Stephanie McMahon added further fuel to the intense conflict, resulting in Triple H’s involvement.
This intense animosity carried through the WrestleMania season. Orton made a major splash by winning the 2009 Royal Rumble, while Triple H secured the WWE Championship at the Elimination Chamber event that year. The two clashed at WrestleMania 25, with Triple H ultimately retaining the title in a high-profile encounter.
However, the storyline didn’t end there. At the following pay-per-view, Backlash, Orton, along with his Legacy teammates Ted Dibiase and Cody Rhodes, defeated the team of Triple H, Shane McMahon, and Batista. This victory crowned Orton as the new WWE Champion, marking a crucial turning point in his career that helped him rise as one of the greatest WWE superstars in history.
Orton’s feud with the McMahon family not only showcased his talent as a performer but also solidified his reputation as a dominant heel in WWE programming. The rivalry remains a key chapter in wrestling history due to its intensity and the career milestones it created for all involved.
Impact and Legacy of Orton’s WWE Storyline with the McMahons
Randy Orton’s involvement in one of WWE’s most controversial segments and his ongoing feud with the McMahon family helped define his persona as The Viper. The awkward kiss with Stephanie McMahon, witnessed by Vince McMahon and Triple H, symbolized the extreme lengths Orton went to portray his character, adding realism and heat to the storyline.
This chapter in Orton’s career boosted his visibility and credibility, ultimately influencing future plots and cementing his place as one of the ring’s most notorious villains. The moment is often remembered by fans and insiders alike as a compelling example of wrestling’s blend of drama and athleticism, demonstrating how tight storytelling can elevate a superstar’s stature.
As WWE continues evolving, Orton’s legacy from this period serves as a blueprint for how impactful character work and bold storytelling can propel wrestlers to iconic status. The enduring fascination with these confrontations underscores their importance not only at the time but in shaping WWE’s narrative landscape going forward.
Our Reader’s Queries
Q. Has John Cena ever beaten Randy Orton?
A. Cena and Orton have faced each other 21 times, and nine of those were championship matches. Cena has a record of 13 wins, 7 losses, and 1 draw against Orton. However, Orton has a slight edge in title matches, leading 5 to 4.