The Player’s Box | Episode 19 – Mini Episode: Fan Questions!

Date: December 30, 2025
Hosts: Madison Keys, Jessica Pegula, Jennifer Brady, Desirae Krawczyk

Episode Overview

In this special mini episode, the quartet of Madison Keys, Jessica Pegula, Jennifer Brady, and Desirae Krawczyk take a break from their holiday downtime to answer a volley of quirky, candid, and insightful fan questions. Listeners are given a courtside seat to playful banter, behind-the-scenes camaraderie, and the real-life challenges and joys of being a tennis pro—from workout pain to period hacks, exhibition drama, and even who’d crash (or land) a plane.

Key Discussion Points

1. Fantasy Doubles: Who Would You Partner With?

[01:32 – 04:13]

• Desirae would pick Jenny for her “kick serve and heavy forehand.”
  “I just feel like a lot of girls aren't used to a kick serve, and that is just, I think, a really big weapon. But also your forehand.” – Desirae Krawczyk [02:23]
• Maddie wants DEZ as a partner:
  “I have no idea when to go, so I would want her to just kind of order me around, lead the pack.” – Madison Keys [02:55]
• Jess would also choose DEZ for fun, angles, and lefty creativity in exhibition settings.
• Jenny leans toward Jess for a “giggly type session,” joking about pegging Dez with a ball.
• Banter ensues about “choosing violence” and hangriness among the group.

2. Emergency in the Skies: Who Would Land the Plane?

[04:15 – 05:24]

• The group reluctantly imagines who’d take control if the pilot passed out.
• Unanimous vote for Jess because of her calmness and “gamer skills.”
• Jess’s husband Taylor has a flight simulator; the group trusts him too!
• “He's like, I got it. Just get away.” – Jess Pegula about Taylor [05:22]

3. Brutal Workouts & Mile Racing Predictions

[05:25 – 09:35]

• Hardest Non-Tennis Workouts:
  • Des: Track and cardio Pilates.
  • Jess: Versa climber and assault bike.
  • Jenny: An impossible assault bike workout with “no breaks.”
  • Maddie: “During my four hundreds the other day…I hit like 186 [heart rate]. I think I’m gonna die.” – Madison Keys [06:08]
• Hot girl incline walks, weight vests, and future “accessorized” walking ambitions are joked about.
• If racing a mile… Maddie would win. She’s been training; others haven’t run a mile since college.
  • “I ran a mile more recently than the rest of us, honestly.” – Madison Keys [08:26]

4. Periods on Tour: Candid Reality

[09:40 – 11:54]

• Honesty about how hard it is to manage periods with travel and training.
• Main strategies: tracking cycles, doubling iron and red meat, and hydration.
• Travel, birth control, and athletic load make cycles unpredictable.
  • “No matter what you're trying to do…never really seems to work out.” – Madison Keys [10:29]
• Jess notes athletes are more injury-prone the week before their period.
• “So basically we have no idea what we're doing. We're just hoping and praying.” – Jess Pegula [11:49]

5. Jess’s Puppy Name Saga

[12:26 – 14:28]

• Fan wonders why Jess didn’t name her new puppy “Jenny.”
• Jess quips: “I didn't consider Jenny, but Jenny definitely considered Jenny.” [12:39]
• Mabel the puppy’s name was indirectly inspired by TV and friends’ other pets.
• The group has fun with puns (“Maybe it’s Maybelline?”).

6. Changeover Jams: To Dance or Not to Dance?

[14:28 – 15:55]

• All admit to “bopping” or subtly moving to good songs during changeovers.
• Maddie mentions caution after seeing a player get distracted and lose focus post-dance.
  • “I don’t ever want to be that…So I try to, like, overly lock in, but in my head, I’m like, this is a good song.” – Madison Keys [15:33]
• Exception: If it’s Shania Twain, Maddie must bop.

7. The College vs. Pro Decision

[15:55 – 17:40]

• Jenny: Candid admission, “I wasn’t good enough to go pro.”
• Maddie: “I went pro too early, so it wasn’t really a conversation.”
• Jess: Hated school, so went pro at 17.
• DEZ: Chose college for financial reasons, embraced the needed growth.
• Both Jenny and Jess reflect on the personal value of time in college.

8. Encore Interviews: Best and Worst Questions

[18:11 – 19:53]

• Pet peeves: Being asked about their next opponent just minutes after a hard match.
  • “…they’re already worrying about the next match, and half the time you don’t even know who you’re playing.” – Madison Keys [19:53]
• They prefer interviews with people who “actually know you.”

9. Surviving on Tour with… Frying Pans?

[19:53 – 21:46]

• Who would survive longest if rackets are replaced with frying pans?
  • Unanimous vote for Jenny—she’s adaptable.
  • The group jokes about trying it at their next practice.
• Storytime: Jenny’s “play to win” attitude in training Dingles brings laughs.

10. Movie Genres, Pirate Jokes & Personality Types

[21:50 – 24:52]

• Movie genre alter egos:
  • Jenny: Jim Carrey-style comedy.
  • Dez: Rom-com/Hallmark cheesiness (with dad jokes).
  • Jess: Dry comedy, satire.
  • Maddie: Mystery/“Knives Out” type.
  • “You start and you're, like, rolling your eyes, and by the end, you have like a little tear…100% me.” – Desirae Krawczyk on Hallmark movies [24:32]
• More lighthearted joking about Netflix Hallmark roles for Dez.

11. How Their Personalities Show Up in Their Game

[25:02 – 28:28]

• Jenny: “I play with my heart on my freaking sleeve…it’s freaking pulsing.” [26:12]
• Maddie: “No nonsense,” focus on “next point,” but with bursts of emotion.
• Jess: Even-keeled and present.
• Dez: “Moody,” bubbly and smiley one moment, fiery the next.
• The group pokes fun about snacks and hangriness, riffing on Dez’s snacking habits.

Notable Quotes & Memorable Moments

• “We just hope and pray.” —The group, on managing periods on tour [09:55]
• “I just feel like a lot of girls aren’t used to a kick serve…” —Desirae on Jenny’s game [02:23]
• “I could never complete [the assault bike sets] in the minute…I just went continuous.” —Jenny Brady [07:02]
• “I play with my heart on my freaking sleeve.” —Jenny Brady [26:12]
• “Maddie would be a Knives Out movie.” —Group, on movie genre alter egos [23:42]

Segment Timestamps

• Doubles partners fantasy: 01:36 – 04:13
• Landing the plane scenario: 04:15 – 05:24
• Hardest workouts & mile run: 05:25 – 09:35
• Managing periods: 09:40 – 11:54
• Puppy naming debate: 12:26 – 14:28
• Changeover jams and dancing: 14:28 – 15:55
• Pro vs college decisions: 15:55 – 17:40
• Encore interview questions: 18:11 – 19:53
• Frying pan survivor: 19:53 – 21:46
• Movie genre personalities: 21:50 – 24:52
• Court personality reflections: 25:02 – 28:28

Final Thoughts

This mini-episode offers an unfiltered, endearing, and often hilarious glimpse into the world of top women’s tennis, highlighting the friendships, quirks, and realities behind the baseline. Each question brings out both the athletes’ competitive edges and their offbeat humor—whether they’re discussing mile sprints, snacking, or why no one will ever name a puppy “Jenny.” It’s a lively listen for fans craving more than just match stats.