The Player's Box – Episode 4

Dating on the Tour, Travel Pet Peeves & Best Slam
Hosts: Madison Keys, Jessica Pegula, Jennifer Brady, Desirae Krawczyk
Release Date: September 16, 2025

Episode Overview

In this episode, the four WTA pros give fans an inside look at tennis life off the court, with candid and often hilarious discussions about dating while on tour, travel inconveniences and pet peeves, must-haves for globetrotting, plus an ultimate ranking of Grand Slam player facilities and food. The episode wraps with lively fan Q&A, including the dream shot swap and walk-on anthem picks.

Key Topics & Insights

1. Dating on the Tour

• Limited Options & Awkward Encounters

  • The players lament the tiny dating pool: “Your options are very slim. It’s like another tennis player or someone you’ll never see, ever. A fan!” (Jessica Pegula, 01:03)
  • Funny anecdote: Muguruza marrying a fan she met walking in Central Park (“He was very handsome. So I just kept talking to him. …and they got married!” – Pegula, 01:14)
  • Most players say they tried to avoid dating another pro, but “I married one.” (Desirae Krawczyk, 02:13), “Both of you!” (Brady, 02:17)

• Tour Life Reality

  • Long-distance is standard: “We all physically do long distance in a way.” (Krawczyk, 06:15)
  • On maintaining relationships: FaceTime is essential, though not perfect—“I get sick of holding the phone.” (Pegula, 03:28), “Whoever you date, Jenny, needs to love FaceTime. That’s a deal breaker.” (Keys & Pegula, 04:28)

• The Coaching Dilemma

  • Blurred lines when partners give tennis advice: “It depends what tip and how you say it. The tone and delivery is what makes it work or not.” (Krawczyk, 07:24)
  • “Even though you were right, I feel like you should have hugged me first before you told me—or during.” (Keys, 08:53)

2. Travel Stories & Pet Peeves

• Flight Itinerary Chaos

  • Players describe marathon travel plans—“Florida to LA, LA to Hong Kong, then drive to Shenzhen… I think I land at like 7am so Monday is going to be an absolute grind for me.” (Pegula, 14:39)
  • Jenny flies early just to hang out with Maddie in LA: “Jenny’s literally flying early so she can come spend time with you.” (Pegula, 16:29)

• Travel Pet Peeves

  • Early Line-Uppers:
    “Group four is three to five and they’re literally in the boarding line waiting to board, but they still haven’t called preboarding. That is my biggest pet peeve.” (Brady, 17:00)
  • Faking Pre-boarding:
    Jenny’s “confession” about pretending to need extra time to board with four items: “I’m limping…she needs extra time…Okay, thanks.” (Brady & Pegula, 20:54)
    “Advantage: Jenny.” (Keys & Brady, 20:55)
  • Baggage Claim Chaos:
    “People just stand in front of you…so everyone just hovers, and when it’s your time you just grab your bag and go ‘Oh, sorry, didn’t see you there.’” (Brady, 21:46)

• Travel Essentials

  • Must-bring items: snacks, matcha kits, face masks, “my LED face mask.” (Keys, 23:46), “I bring my own matcha kit…to make it feel homey.” (Krawczyk, 23:31)
  • Packing strategy: “I actually got my travel down to only two check-in bags, but I think I might go back to three for Asia…” (Pegula, 23:03)

3. Fan Q&A & Favorite Tennis Memories

Notable Quotes & Moments

• On Stealing Each Other’s Shots [29:03]

  • “I want Des’s volleys.” (Keys, 29:03)
  • “I would take Des’s chip lob. I literally can’t lob to save my life.” (Brady, 29:33)
  • “I’d probably take Maddie’s serve, Jesse’s backhand—solid as a rock.” (Brady, 30:09)

• Grand Slam Player Facilities, Food & Gyms [32:43]

  • Universal agreement: Australian Open wins for best facilities and food.
    • “Facility? Grand Slam? Australia.” (Keys, 33:00)
    • “They have three floors of food…pasta, grill, salad bar, sushi…” (Brady, 33:12)
    • “The locker rooms are huge, so nice. It’s all brand new and updated.” (Keys, 34:03)
  • US Open: More congested, but the new indoor area helps. “It’s not that big of a space.” (Krawczyk, 35:30)
  • Roland Garros: Nice, but farther. “You have to take a car, but you can just stay at the Jambon there and not go on site.” (Pegula, 35:39)
  • Wimbledon: Orangi for backup facilities, but site navigation is a grind. (Pegula, 36:33)
  • Gyms: “Australia has like nine gyms now…so much space!” (Brady, 37:17)

4. Walk-on Court Songs [37:58]

• Seven Nation Army – Jennifer Brady
• “I think I want to go with like a 50 Cent…would have to bleep it out, but…” (Pegula, 38:05)
• “Shania Twain—Let’s Go Girls!” (Keys, 39:07)
• Enter Sandman (for Billie Jean King Cup entry), and Mr. Brightside (“That song [gets] the entire stadium…nuts!” – Brady, 40:25)
• Brady’s ongoing obsession with Bills quarterback Josh Allen is playfully called out by the group (40:54).

Memorable Exchanges & Quotes

• On Tennis Advice at Home

  • “Taylor just tries to tell me to slice more. That’s always his go-to.” (Pegula, 09:49)
  • “My husband is not a tennis player or has no formal background…but that’s usually just his advice to me.” (Pegula, 10:24)

• On Coping With Unique Opponents

  • “Please, give me a normal topspin forehand!” (Keys, 12:21)
  • “So tight…the whole first set” against ‘choppers’ like Moni and Ito. (Keys, 12:44)

Timestamps for Key Segments

• Dating on Tour: 00:54 – 06:41
• Long-Distance and FaceTime: 03:43 – 07:04
• Partner as Coach/Fighting Over Advice: 07:10 – 09:36
• Travel Logistics (China Trip): 13:30 – 15:57
• Travel Pet Peeves: 16:47 – 23:46
• Travel Essentials: 23:46 – 24:34
• Maddie’s Beat Bobby Flay Appearance: 24:55 – 28:37
• Fan Q&A: Stealing Each Other’s Shots: 29:03 – 32:40
• Grand Slam Facilities/Catering/Gyms: 32:43 – 37:29
• Walk-on Court Songs: 37:58 – 41:50

Conclusion

This episode is a lively, laugh-filled deep dive into the realities of tour life. From the awkwardness of finding romance on the circuit to everyday gripes at the airport and cherished food options at major tournaments, The Player’s Box keeps it real, relatable, and fun. Don’t miss the end-of-episode fan Q&A: “If you could steal one shot from each other…?” reveals their on-court envy, and the music talk gives a peek into their pre-match mindsets.

For future questions, fans are encouraged to DM the podcast on Instagram or email—listen next Tuesday for more behind-the-scenes tennis stories!