The Player’s Box | Episode 11: Riyadh, Egg Freezing & Embarrassing Moments

Release Date: November 4, 2025
Hosts: Desirae Krawczyk, Jennifer Brady, Madison Keys, Jessica Pegula

Episode Overview

In this episode, the squad—Desirae, Jenny, Maddie, and Jess—brings listeners behind the scenes at the WTA Finals in Riyadh. They dive into travel fails, share personal mishaps, give a humorous account of locker room life, answer candid fan Q&As, and discuss the real-life process of egg freezing. The conversation is packed with laugh-out-loud anecdotes, inside tennis gossip, and honest takes on the realities (and absurdities) of life on tour.

Key Discussion Points & Segments

1. Unforced Error of the Week (00:39)

Each host shares their funniest or most cringeworthy mishap from the week:

• Jessica Pegula: Perpetually losing the transportation game in Riyadh.

  “I keep leaving before everybody, and everyone keeps getting there before me. So I’m losing on all angles, clearly.” (01:43)

• Jennifer Brady: Busted picking up takeout in pajamas, immediately spotted by tennis peers.

  “I look chopped, like really bad.” (03:12)
  “Sloan’s mom is there... and I was like, oh my gosh, I’m so embarrassed.” (03:13)

• Desirae Krawczyk: Mistakes a carbon monoxide alarm for birds chirping; changes every fire alarm battery in her house.

  “I thought it was birds, like, in sync for every 40 seconds.” (03:59)
  “Ended up being a small carbon monoxide tester thing that I just literally unplugged.” (03:59)

• Madison Keys: No personal mistake, but “honorable mention” to tennis drama:
  Recounts social media banter after Zizou Bergs moonwalked post-win, facing a trolling Riley Opelka.

  “We should just start sending Riley all the screenshots of, like, sports betters... and he can just troll them back.” (07:15)

Award for best unforced error goes to Desirae for her “birds” confusion (09:22).

2. Concert Stories & Bucket List Shows (10:08)

The group talks favorite concerts, recent Jonas Brothers show with Kevin Jonas cameos, and music icons they dream of seeing.

• Jess Pegula: Reminisces about meeting Kevin Jonas at the US Open:

  “He was so, so nice... his kids are super into tennis.” (11:41–12:45)

• Favorites:

  • Madison: Beyoncé (“Saw her in London this year. Bucket list item finally checked off” 13:02)
  • Desirae: Britney Spears, Kelsea Ballerini (travelled to Portland to see her—16:52)
  • Jenny: Kings of Leon (“number one favorite band of all time” 14:29)
  • General: Taylor Swift, Carrie Underwood, Paramore mentioned as top concerts.

• On concerts vs. streaming:

  “I’m not a huge concert person. I’d rather just listen in my car.” – Jenny (13:27)

3. Riyadh & WTA Finals: Behind-the-Scenes (17:52)

Jess and Maddie give an insider account of arriving, practice schedules, and the iconic annual photoshoot:

• Dress fittings drama (19:09–22:39):

  • Huge room, 200+ dresses, lots of laughs.
  • Coco Gauff hilariously disapproving of Jess’s ruffled attempt:

    “She just goes, no, no.” – Jess (20:07)
    “Coco definitely approved my look... we both got the Coco stamp of approval.” – Maddie (23:22)

• Tournament logistics:

  • Group stage details—Serena Williams and Steffi Graf groups, loaded with talent (24:11–25:05).
  • On group toughness:

    “I saw my group and I was like, wow, that’s tough. And then I looked at the other one and was like, oh, that sucks too.” – Maddie (25:11)

4. Egg Freezing: Real Talk (25:21)

Desirae shares her experience starting the egg freezing process—addressing nerves, hormones, anti-doping, and the new WTA maternity policy.

• Desirae’s journey:

  “It’s 10 days worth of shots... I’m a little nervous. I’m curious to see how my emotions will be and how the hormones will be flowing.” (25:50)
  “The WTA... came out with the funding... It’s amazing that WTA has that funding... I have a few of my friends who have gone through it.” (27:35)

• On the process and WTA protocol:

  “You have to just make sure you're doing it right. Because the worst thing could happen is... you take something that you're trying to do the right thing of and then you get caught for it.” (28:45)

• Support for others:

  “If you have the opportunity and the funding to do it, it’s great. You should do it... It’s like an insurance policy in a way.” (30:01)

5. Most Embarrassing Locker Room Moments (31:17)

Candid confessions about weird, awkward, and memorable moments behind the scenes:

• Jenny: Awestruck and flustered when Serena Williams arrived at neighboring locker.

  “I was holding these boxes... I just, like, literally just... jump over the bags and just leave.” (32:43)

• Desirae: On shower towel fails and naked locker room dashes:

  “Sometimes it'll just be a random person... ‘hey, can you give me a towel? I really don't want to run around here naked’.” (34:25)

• Maddie: Terrorized by a cockroach after a night match; scared a security guard.

  “I jumped up on top of one of the benches and started just screaming bloody murder. The poor security man came running in... ‘are you okay?’.” (35:23)

6. Courtside Snaps & Sideline Sarcasm (36:15)

Have they ever snapped at their coaches during a match?

• Desirae: Sarcastic thumbs up after a failed play suggestion from coach Craig.

  “I gave him the thumbs up and I went, ‘thanks.’” (37:09)
  “The thumbs up was like, yeah, good, good.” (37:17)

• General consensus: Thumbs up in tennis = not actually “good job.”

  “If anybody ever sees someone giving a thumbs up to their box... it's not positive.” – Jess (38:08)

• Jenny (on sideline pet peeves as a junior):

  “My mom would come to my matches... I could hear her bracelet or, like, her smacking gum... I’d be like, take your bracelet off!” (40:09)

7. Fan Q&A Lightning Round (41:17)

Have any hosts ever been in a serious fight? (41:32)

• “There have been times in the chat, Jenny and I are going back and forth... then Maddie will chime in, like, ‘okay, guys, that’s enough’.” – Desirae (42:27)
• “We’re all pretty direct and upfront... If there’s anything that bugs us, it’s just like, ‘Hey, we need to talk about this?’” – Maddie (43:05)

Favorite Films (45:28)

• Desirae: She’s The Man, How To Lose A Guy In 10 Days, Hocus Pocus, Frozen
• Maddie: Inside Out 2, Encanto, Moana 2, Julia Roberts films (Parent Trap, Something’s Gotta Give)
• Jess: Mulan, Miracle, Shawshank Redemption, Jerry Maguire
• Jenny: She’s The Man, The Dark Knight Rises, White Chicks, Shrek

“When I think of favorite movies, I think of what’s a movie I’ve watched more than three times? That’s my favorite.” – Jenny (49:22)

How do you do your laundry on tour? (51:12)

• “Usually, at tournaments, they provide laundry for us... hopefully you don't get anyone else’s underwear or boxers.” – Desirae (51:15)
• “If it's a tournament I trust, I’ll drop it off. But I’ve gotten burned by burned shirts and shrinkage…” – Maddie (52:00, 52:09)
• “You know the tournaments you don’t bring your favorite things to because you might never see them again.” – Maddie (51:50)

Why wear jewelry on court? Aerodynamics? (56:13)

• “I’ve never thought about it, to be honest. I’m a 'more is more' kind of person when it comes to jewelry... If I don’t get to a drop shot, I doubt it’s my jewelry.” – Maddie (57:16)
• “Yeah, more jewelry the better.” – Desirae (58:03)
• “Sometimes I'm like, I really need to cut my hair... but never thought about jewelry slowing me down.” – Jenny (58:30)

Memorable Quotes & Moments

• On travel disasters:
  “My unforced error, which I think I've already told you about, I've decided is going to be, is that I have been utterly failing at transportation here in Riyadh.” – Jess (00:39)
• On egg freezing:
  “It's like an insurance policy... You don't know how long you'll be playing for and if you want to continue with your career.” – Desirae (30:01)
• On sideline sarcasm:
  “If anybody ever sees someone giving a thumbs up to their box… it's not positive.” – Jess (38:08)
• On group chat bickering:
  “Jenny and I are going back and forth... then Maddie will chime in, ‘okay, guys, that’s enough’.” – Desirae (42:27)
• On locker room etiquette:
  “I had to leave the area. Like, she's here, and I have to leave.” – Jenny (32:26)

Timestamps for Key Segments

• 00:39 – Unforced Error of the Week
• 10:08 – Concert stories / Jonas Brothers & bucket list concerts
• 17:52 – Riyadh arrival & WTA Finals dress fittings
• 25:21 – Egg freezing process
• 31:17 – Most embarrassing locker room moments
• 36:15 – Sideline coach snapping & sarcasm
• 41:17 – Fan Q&A (fights, films, laundry, jewelry)

Tone & Vibe

Chill, candid, and peppered with sharp humor and self-deprecation. Every story—whether about tennis, life, or mishaps—serves as a reminder that behind the superstar athlete image are relatable women dealing with the same frustrations, logistics, and laughs as everyone else.

For more behind-the-scenes stories, player banter, and listener Q&A, subscribe and tune in every Tuesday to The Player’s Box Podcast.