Randy Orton is one of WWE's longest-serving superstars. In 2002, The Viper made his main roster debut when many of his current co-workers, including Charlotte Flair, were still in high school.
Flair was just 16 years old when Orton competed in his first televised match shortly after WrestleMania 18. The Queen's legendary father, Ric Flair, worked for WWE at the time. He once allowed his daughter to travel with him on a European tour, where she hung out with Orton and several other WWE stars.
In the 2017 book Second Nature: The Legacy of Ric Flair and the Rise of Charlotte, the multi-time women's champion wrote about Orton. She confessed to having a crush on the former Evolution member when she was in high school, and he was one of wrestling's rising stars:
"After the show that night, my parents let me 'go out with the kids,'" Charlotte Flair wrote. "I was with Stacy [Keibler], Randy Orton, Victoria, Hurricane Helms, and Torrie Wilson. Since I was in Europe, I was legally allowed to enjoy drinks with them. They watched over me like I was their little sister, which was unfortunate for me because, in high school, I had a crush on Randy. I hoped, as a high school girl would, that he'd see me in another way, not as his little sister. What high school girl wouldn't? That didn't happen."
— Charlotte Flair (@MsCharlotteWWE) April 24, 2023
Two decades on, Flair married current AEW wrestler Andrade El Idolo in 2022. Meanwhile, Orton has been married to his wife Kim since 2015.
Charlotte Flair learned a lot on tour with WWE
Although she watched her father in WWE for many years, Charlotte Flair did not join the company herself until 2012. She has gone on to wrestle at hundreds of shows, including untelevised live events.
❤️ @RicFlairNatrBoy pic.twitter.com/COBpUSS964
— Charlotte Flair (@MsCharlotteWWE) April 20, 2023
Flair felt that her European tour trip as a teenager gave her a good understanding of the hard work that goes on behind the scenes:
"The overseas tours helped me to understand the enormity of WWE productions. The number of trucks, backstage crew, pyrotechnic teams, lighting crews, catering professionals, medical staff, the roster of superstars (…) to see the shows in Dublin two nights in a row and then to experience the shows immediately following in Manchester and Birmingham with the same grandeur was all incredible."
Flair also wrote about the childhood crush she had on another one of her father's famous friends, wrestling icon Sting.