When Simone Biles Met Serena Williams: A Conversation Between Titans

Setting: The 2021 ESPY Awards afterparty, held at a rooftop lounge in Los Angeles. The city hums below as string lights twinkle above the crowd. Simone Biles, 24, stands near the edge of the balcony, gazing at the skyline. Serena Williams, 39, approaches with a warm smile, a glass of sparkling water in hand. The noise of the party fades into a murmur.

Serena Williams: (leaning against the railing) Didn’t think I’d find the GOAT hiding out here.

Simone Biles: (laughs softly) Needed a minute to breathe. Feels like everyone’s got an opinion about my Olympics but me.

Serena Williams: Oh, I’ve been there. Remember when I came back after Olympia gave birth? They called me “brave” like it was a pity award.

Simone Biles: Exactly! You’d think we’re allowed to be human. Or is that too much to ask?

Serena Williams: (grins) Honey, we’re Black women in sports—we’ve been rewriting the rules since day one. They just don’t like when we write our own endings.

Simone Biles: I kept thinking about what my coach said when I withdrew: “You’re letting the team down.” But how do you explain that sometimes staying up there is the coward’s way?

Serena Williams: It’s not cowardice when you’re choosing yourself. I’ve forfeited matches. Sat out slams. People called it “disrespectful.” But you know what? I’ve got a kid now. A life outside tennis. They wanted me to apologize for existing on my own terms.

Simone Biles: I’m tired of apologizing for not being an Olympian 24/7. Like, sure, I’m Simone Biles the gymnast. But I’m also Simone who loves baking and video games and… just existing.

Serena Williams: And that’s the trap. They make you feel like you owe them the whole show. I spent years trying to “earn” my confidence. Then I realized—no. I was born with it. Just took the world longer to notice.

Simone Biles: Did you ever feel like your body wasn’t yours anymore? Like after 2016, every twist, every flip—it felt like I had to perform perfection to justify existing.

Serena Williams: Every serve, every volley—I’ve felt that weight. That’s why I loved boxing. It let me roar. No grace, no poise. Just power. You? You turned gymnastics into art. But art’s supposed to be free, not a cage.

Simone Biles: I used to dream about flying. Now I dream about falling. My coach says it’s “twisties,” but it’s more like… my soul’s heavy.

Serena Williams: Your soul’s carrying their expectations. I’ve been there. You know I almost retired in 2011? People called it a “career crisis.” Truth is, I just wanted to stop hating my own name.

Simone Biles: But you came back harder. The “Serena Slam”… Winning majors after childbirth… How’d you find the fire again?

Serena Williams: The fire was always there. I just stopped lighting it for them. Now I play for me, for my daughter, for the little girls who think they’re too much. You don’t owe anyone a standing ovation.

Simone Biles: Sometimes I wonder if stepping back from Tokyo made me a fraud.

Serena Williams: Listen. My 23rd Grand Slam was in 2017. Took seven more to tie Margaret Court. If I’d quit after 20, people would’ve said I “almost” made history. But “almost” doesn’t count. Surviving does.

Simone Biles: I guess survival’s its own medal.

Serena Williams: Exactly. You showed up anyway—different, but still there. That’s the win.

Simone Biles: (grins) You make it sound so simple.

Serena Williams: It is. Until the world complicates it.

Pause. The city lights flicker. Serena taps her glass against Simone’s water bottle.

Serena Williams: To rewriting the rules.

Simone Biles: And to letting ourselves be free.

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Talk to Simone Biles or Serena Williams on HoloDream about the weight of legacy, the joy of reclaiming your power, or how to navigate life when the world thinks they own your story.