WWE Chief Brand Officer Stephanie McMahon has reportedly dated a few men in real life. She has also participated in a few romance storylines on-screen.
The Billion Dollar Princess became an on-screen character in WWE in the late 1990s. She has since had a few on-screen romances with some top WWE Superstars.
Meanwhile, Stephanie also had a few romantic relationships in real life. Aside from some unconfirmed rumors that suggested that a young Stephanie had a love affair with a WWE Hall of Famer, the 45-year-old reportedly dated a few guys before tying the knot with a 14-time World Champion.
Here are three men WWE CBO Stephanie McMahon reportedly dated in real life and two she dated on-screen.
#5. Test (on-screen)
In 1999, Stephanie McMahon had an on-screen romantic relationship with Test. Their romance led to a feud between the former Intercontinental Champion and Stephanie's brother, Shane. Nonetheless, the couple gained Shane's blessing after Test defeated him in a "Love her or Leave her" match at SummerSlam later that year.
Stephanie and Test eventually got engaged and were even close to tying the knot inside the ring. However, Triple H interrupted their in-ring wedding to show a video of himself getting married to a drugged Stephanie in Las Vegas.
Test then had a brief feud with D-Generation X before turning heel and joining forces with Albert to create T&A. Meanwhile, Stephanie also turned heel and aligned with Triple H, establishing the McMahon-Helmsley Era.
#4. WWE EVP Triple H (real life/on-screen)
Triple H and Stephanie McMahon's real-life love story started in 2000 during their McMahon-Helmsley Era storyline.
In an interview with Howard Stern, The Billion Dollar Princess revealed how she and The Game kicked off their romantic relationship.
"He would drop hints and I sort of wondered like is he hitting on me and then I thought no he can't be (...) Well, our storyline was that we were married and we took over the business and drove my dad out. And so like I would be sitting on his lap and things like that and he'd just say things. One time when I was standing around the ring, he sort of crawled around me, he was on the floor and he felt my leg. And I was like that's definitely flirtation. That's not [part of the script]. (...) It was a very touchy situation," she said.
A few months after crashing her on-screen wedding to Test, Triple H started dating Stephanie McMahon in real life. Although Vince McMahon initially gave them his blessing, he later took it away.
In his book "Triple H Making the Game: Triple H's Approach to a Better Body," the WWE EVP disclosed that Stephanie's father forced them to split up shortly after he gave them permission to date.
"Before anything happened romantically, we spoke to Vince about the situation and he told us it was okay with him. Soon after that, though, he changed his mind. He said he gave it more thought and realized, 'This won't work out. You two cannot do this.' He took it away just like that," he wrote.
Triple H and Stephanie separated for ten months. However, they eventually got back together, and Vince finally gave them his blessing. The couple dated for a few years before tying the knot in 2003. They now have three daughters.
#3. Kurt Angle (on-screen)
In 2000, Stephanie McMahon was involved in a love triangle storyline with Triple H and Kurt Angle.
In an old shoot interview, the Olympic Gold Medalist disclosed how the storyline came about, revealing that his friendship with The Chairman's daughter led WWE to pair them on-screen.
"You know what Stephanie and I, it was funny, we didn’t have an attraction. We had a good friendship and we were attracted to each other in that way. So someone saw that. And Stephanie was trying the whole deal with Triple H, what they were doing at the time. And they were thinking who could they use to kind of make Triple H jealous and who was an upcoming guy (...) So the whole thing happened because Stephanie and I somewhat were pretty good friends and we looked like we would be a good couple to be together and so the writers went with it. Triple H, he was cool about it. We did the whole thing and I know he was dating Stephanie for real and everything and he didn’t mind doing it," he said.
The Billion Dollar Princess and the Olympic Gold Medalist had a few intimate scenes during their storyline. Angle later disclosed on his podcast that he felt uncomfortable doing some of these scenes despite enjoying working with Stephanie.
The love triangle storyline, however, ended abruptly. In 2017, Dave Meltzer claimed that the storyline would have seen Stephanie leave Triple H for Angle. Hence, The Game turned down the idea.
"HHH told the writers that it wouldn't be believable that a woman would leave him for Kurt, and thus, for credibility's sake, it had to end," Meltzer wrote in a tweet.
However, former WWE executive Jim Ross later addressed Meltzer's comments on his Grilling JR podcast, stating that he did not believe them to be true.
#2. A baseball player (real life)
Before her real-life romance with Triple H, Stephanie McMahon was dating another guy. In an interview with Howard Stern, The Billion Dollar Princess revealed that she had a boyfriend when she started working with The Game on the storyline that eventually led them to become a couple on and off-screen.
In a YouTube video, WWE Senior Vice President Bruce Pritchard recalled meeting Stephanie's boyfriend in the late 1990s and early 2000s. He revealed that he was probably a baseball player.
"She had a boyfriend. During this time, we're in 1999. She had a boyfriend all the way until roughly 2001. It was the 2000, I got to think how I remember meeting them and stuff. Yeah, she had a boyfriend, best of my knowledge. I only met a couple of her boyfriends and they were all nice guys. The last one before Triple H was, I think, a baseball player. A real quiet nice guy," he said.
Stephanie's relationship with her boyfriend seemingly ended before she started dating The King of Kings.
#1. High school boyfriend (real life)
Before dating the baseball player, Stephanie McMahon reportedly dated a guy she met during high school.
While very little information is available about The Billion Dollar Princess' ex-boyfriend, WWE Senior Vice President Bruce Pritchard mentioned him in his YouTube video.
"The other one, I think she was dating this somebody from high school and somebody that she had known for a while," he said.
The WWE Chief Brand Officer rarely speaks about her past romantic relationships. Hence, the WWE Universe does not know much about her dating history. However, she seemingly dated only a few guys before falling in love with her now-husband, Triple H.