Features

The Stephanie McMahon You Never Knew: Failed Relationships, Health Struggles & Personal Setbacks

By Ahmed Hamdy • Published Aug 21, 2025 19:00 EDT
Young Stephanie McMahon

Stephanie McMahon’s past is lesser-known to the WWE Universe.

The Billion Dollar Princess was introduced to WWE fans in 1999, when she became an on-screen character. Over the next few decades, the 48-year-old cemented her legacy as one of the greatest heels in the company’s history.

While she participated in many historic storylines, Stephanie also held several backstage positions, including chairwoman and co-CEO, before resigning in January 2023.

Another side of Stephanie’s life that is well-known to the WWE Universe is her relationship with Triple H. The couple’s on-screen romance turned real in late 1999 and early 2000. They dated for a few years before marrying in 2003. The Game and The Billion Dollar Princess now have three daughters.

As much as Stephanie’s life seems like an open book since her first appearance on WWE TV, her pre-WWE fame past is rarely talked about. Only a few old interviews with The Billion Dollar Princess have shed some light on who Triple H’s wife was earlier in her life.

Stephanie McMahon’s Dating Life Before Triple H

Little is known about The Billion Dollar Princess’ relationships before The Game. However, glimpses of The Billion Dollar Princess’ love life were revealed over the years. In a video from the #DearMe Girl-Power campaign in 2015, Stephanie McMahon revealed that her prom date was a guy she disliked.

When that guy, you know the guy, the guy we don’t like asks you to the prom this time say no.

Bruce Prichard has also previously spoken about Stephanie’s love life, recalling her dating one of her high school colleagues and a baseball player.

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…The other one, I think she was dating this somebody from high school and somebody that she had known for a while. [H/T: FirstSportz]

In an old interview with RAW Magazine, Stephanie opened up about finding difficulty in her dating life, describing herself as a “hopeless romantic.”

Stephanie McMahon Had A Hard Time In High School Because Of Her Father

In her interview with RAW Magazine, Stephanie McMahon recalled her high school days, remembering that her father was then under federal investigation, while rumors suggested he and her mom were getting divorced.

While The Billion Dollar Princess disclosed that her peers did not treat her differently, it was their parents and some teachers who did. The 48-year-old did not hold back, however, when it came to defending her family.

My peers never really treated me differently; it was their parents or certain teachers. They looked down at me because ‘wrestling’ was definitely percieved as ‘low-brow’ entertainment, and my father was the kingpin. But I am extremely proud of my father, my family’s business and who I am, and I was never afraid to say so, even if it meant launching a completely inappropriate verbal assault on one of my friend’s parents.

Stephanie McMahon Was Forced To Retire From Basketball In 8th Grade

The former WWE Chairwoman competed many times inside the squared circle. What many fans do not know, though, is that Stephanie McMahon was born with a knee condition. She discovered her knee issues after practicing field hockey, basketball, and softball in junior high.

Stephanie revealed in her interview with RAW Magazine that her doctor informed her that she needed a major reconstructive surgery and forbade her from skiing and playing basketball.

I found out my knees weren’t designed very well. I had one knee scoped [arthroscopic surgery], and it didn’t really work. So the doctor told me I needed major reconstructive surgery to move around bones and muscle tissue. I said, “No thank you.” After that, the doctor told me two things I shouldn’t do were ski or play basketball. The Billion Dollar Princess retired from basketball in 8th grade.

While the 48-year-old’s knee condition did not stop her from working out over the years, she recently disclosed that she had taken up jiu-jitsu.

Stephanie McMahon Had A Crush On Ric Flair Growing Up

The Billion Dollar Princess has previously admitted that her three favorite wrestlers were Andre The Giant, The Rock, and Ric Flair. Stephanie McMahon had the opportunity to share the ring with The Final Boss and The Nature Boy in WWE.

During a segment with Flair in 2002, the 48-year-old made a personal admission, stating that she had a crush on the 16-time world champion growing up.

I mean I’ve been watching wrestling since I can remember. And I’ll even admit when I was a little girl, I had a crush on The Nature Boy. But as I grew older, that crush turned into respect.

Stephanie McMahon Tried Her Luck At Songwriting

The former WWE Chairwoman has many talents, but songwriting was not one of them. In her rare RAW Magazine interview, Stephanie McMahon spoke about her love for writing.

The Billion Dollar Princess revealed that she had written poetry and short stories. However, she failed to write song lyrics.

I really love to write. That’s something a lot of people don’t know about me. I’ve written short stories, lots of poetry. I’ve attempted to write song lyrics, though I haven’t been too successful with those. I think I’m a writer at heart.

A few years ago, Stephanie announced that she was finishing her book, “Unreal: Growing Up in the Crazy, Fun Show Business World of WWE.”

Also read: The Dark Side Of Triple H & Stephanie McMahon’s WWE Romance: Breakups, Rumors & Controversy