Stay Winnin'

50 episodes listed below

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Family life, jokes, and the weekly play.

The gist

Stay Winnin' follows Mr. Winner and Mrs. Winner through the small negotiations of family life. Swim lessons, birthday routines, kids' meltdowns, travel nerves, TV spoilers, and anniversary memories all become easygoing conversation with a playful closing lesson.

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About Stay Winnin'

Stay Winnin' captures the texture of family life through relaxed conversation between Mr. Winner and Mrs. Winner. The show is not built around polished segments or big premises. It works because the week itself is enough. A child's swim lesson turns into a story about nerves, encouragement, cold water, and the funny logic of asking for more water after swallowing too much of it. A dental visit becomes a full account of pictures, fluoride choices, a treat across the street, and the meltdown waiting at home. Travel planning opens into conversations about girls' trips, family vacations, parasailing, Devil's Bridge, ocean fears, safety research, and the money that appears after the flights and hotel are already paid. Pop culture slips in naturally. One episode may weigh 112 against Jagged Edge, while another drifts through Bridgerton spoilers, Sweet Sixteen memories, Russell Westbrook fashion, or old hair habits. The marital dynamic carries much of the pleasure. Mr. Winner and Mrs. Winner tease each other, correct each other, lose track of episode numbers, and circle back to the kids with the familiarity of people who know the same stories from different angles. It is funny because it is specific. It is warm because the jokes usually land inside care, not above it. The home setting matters too: unpacked boxes, bath-time accidents, work calls behind closed doors, birthday seasons, anniversaries, and family-only holidays all become part of the show's running record. Episodes can wander, but the wandering feels like the point. The listener hears a household thinking out loud. Guests such as Dr. McQueen Hamilton and Miss Morgan Taylor add another register when the conversation turns toward friendship and travel. A recurring “play of the week” closes many episodes with a short practical takeaway. Stay Winnin' is best for listeners who want a family-and-marriage conversation that values humor, ordinary details, and honest domestic play-by-play over packaged advice.

Made for: Stay Winnin' is for listeners who enjoy casual couple banter, parenting stories, travel talk, and pop-culture side quests. It especially fits people who like family podcasts that feel like sitting near a lively kitchen-table conversation.

What sets it apart: The show turns small household moments into full stories without sanding off the interruptions, corrections, and tangents. Its mix of marriage rapport, parenting logistics, nostalgic pop culture, and the recurring “play of the week” gives it a distinct lived-in shape.

In their own words

We're married. We have three kids. We're just trying to get it right!

Why you'd press play

The dentist visit goes fine; the car-seat exit is where you'll feel seen.

Press play if you want

  • to hear how a tiny parenting decision can take twenty minutes to undo
  • swim-lesson nerves, reassurance, and a child's urgent request for the TV at home
Read the full recommendation in PlayNext →
parenting routinesmarriage banterkids' lessons and meltdownstravel planningbirthdays and anniversariesR&B and pop cultureTV reactionsweekly practical lessons

Talks about

Best episodes of Stay Winnin'

Short reviews from the PlayNext desk, based on the episodes we processed.

EP.112 Swim LessonsApr 12, 2022

A mouthful of water becomes a quiet test of whether a child can steady herself and try again.

The episode turns a swim lesson into a modest but revealing look at how children handle discomfort when a new skill stops feeling fun. One daughter gets water in her mouth, comes out cold, asks for water, takes a few breaths, and returns after being reminded to relax and pay…

EP. 111 Travel 101 feat. Doctor Janelle and Ms. MorganApr 7, 2022

A candid travel chat where parasailing safety, Devil's Bridge, and beach memories define the edge of adventure.

This travel episode keeps vacation planning close to real life, framing adventure through excitement, family needs, and personal limits. The host brings Dr.

"Aries Season" EP. 110Mar 29, 2022

A birthday-week check-in where Aries weather, romance talk, and one very messy bath all land in the same room.

Episode 110 eases into Aries season with birthday-week momentum, changeable weather, and a casual check-in on a series one speaker is still trying to finish without getting spoiled.

"Birthday Season" EP. 109Mar 24, 2022

A warm family conversation where an expensive bicycle, curly hair, and bedtime expose the labor inside ordinary life.

This single-episode review lands as a warm, loosely braided family conversation about preparation, domestic friction, and the way old pop-culture memories can sharpen present-day judgments.

"Check The Calendar" EP.108Mar 15, 2022

A funny, tender family-day review about parenting when routines meet a very tired child.

This single-episode review works best as a small, familiar portrait of a family day losing its shape. A dental visit starts smoothly, with good pictures, fluoride, and a mint toothpaste choice, but the ride home turns into a car-seat standoff over who gets to help.

Podcasts like Stay Winnin'

Episodes

  1. 1

    EP.112 Swim Lessons

    The kids' doctor visit turns into a scale-and-shots comparison, and the parents keep going biggest to smallest.

    Apr 12, 2022·30m·2 clips
  2. 2

    EP. 111 Travel 101 feat. Doctor Janelle and Ms. Morgan

    Hidden gem

    The host interviews two guests about travel, specifically girl travel, discussing planning trips and changes in the travel scene.

    Apr 7, 2022·52m·2 clips
  3. 3

    "Aries Season" EP. 110

    Hidden gem

    A wet diaper turns into "literal shit on the floor" while getting the baby ready for the bathtub.

    Mar 29, 2022·31m·2 clips
  4. 4

    "Birthday Season" EP. 109

    The hosts revisit early-2000s music habits, including Walmart clean albums, LimeWire, Napster, Windows Media Player, and burning CDs with custom track lists.

    Mar 24, 2022·25m·1 clip
  5. 5

    "Check The Calendar" EP.108

    Hidden gem

    The episode turns into a debate about whether the calendar matters if nobody reads it.

    Mar 15, 2022·39m·2 clips
  6. 6

    "Just Don't say Anything" EP.107

    A request for a Spider-Man library book starts a bedtime dispute, prompting the parents to debate sharing and whether an older sibling should have to accommodate crying.

    Mar 8, 2022·36m·2 clips
  7. 7

    "You Awake?" EP.106

    Stay Winnin' EP.106 follows two hosts through a night of children waking and shifting between beds.

    Mar 3, 2022·43m·2 clips
  8. 8

    "Commanders" EP.105

    A New Jersey funeral trip gives the hosts a reason to talk about seeing family they had not seen since toddler years.

    Feb 22, 2022·32m·1 clip
  9. 9

    "Doctor in the House" EP. 104

    Feb 17, 2022·57m
  10. 10

    "Momcation" EP.103

    Feb 9, 2022·31m
  11. 11

    "102 but its 105" EP. 102

    Feb 2, 2022·34m
  12. 12

    "Sharing Bottles" Ep. 104

    Jan 26, 2022·48m
  13. 13

    "Small Jersey" Ep. 103

    Jan 19, 2022·28m
  14. 14

    "Go Under" Ep. 102

    Jan 11, 2022·48m
  15. 15

    "Its a New Year" Ep. 101

    Jan 5, 2022·44m
  16. 16

    "Black love all around" EP. 100

    A married couple celebrates their 100th episode by reflecting on their family life and holiday season.

    Dec 28, 2021·39m
  17. 17

    "No Refills" EP. 99

    Dec 22, 2021·33m
  18. 18

    "Our Coast is the Best Coast" EP. 98

    Dec 14, 2021·46m
  19. 19

    "I'm Slipping, I'm falling" Ep. 97

    Dec 7, 2021·42m
  20. 20

    "Young Old Head" Ep. 96

    Nov 30, 2021·42m
  21. 21

    "You Not a Captain" Ep.95

    Nov 24, 2021·34m
  22. 22

    "Spoiler Alert" Ep. 94

    Nov 16, 2021·40m
  23. 23

    "The Harder They Fall" Ep. 93

    Nov 9, 2021·37m
  24. 24

    "Tech Savvy" Ep. 92

    Nov 3, 2021·36m
  25. 25

    "You Better Figure It Out!" Ep. 91

    Oct 26, 2021·42m
  26. 26

    "TV Land" EP. 90

    Oct 19, 2021·41m
  27. 27

    "White Lotus" Ep. 89

    Oct 12, 2021·43m
  28. 28

    "Back From Vacation, Talking Vacations" Ep. 88

    Sep 28, 2021·38m
  29. 29

    "Short Week" Ep 87

    Aug 24, 2021·33m
  30. 30

    "Missing my Little Family" Ep. 86

    Aug 18, 2021·25m
  31. 31

    "Russel Westbrook Fashion" Ep. 85

    A married couple hosts a weekly podcast sharing updates on their family life, including trip planning and parenting challenges.

    Aug 11, 2021·22m
  32. 32

    "Sexy Beast" Ep. 84

    Aug 4, 2021·27m
  33. 33

    "Daycation" Ep. 83

    A married couple celebrates their anniversary and reflects on their relationship journey.

    Jul 27, 2021·37m
  34. 34

    "We Got a Generator" Ep. 82

    A married couple discusses movies they watched, including Black Widow and The Tomorrow War, and shares family updates.

    Jul 20, 2021·35m
  35. 35

    "Sick and Inside" Ep. 81

    Jul 6, 2021·28m
  36. 36

    "I don't drive with permitees" EP. 80

    A married couple discusses their family's love for sports, including basketball and the upcoming NFL season, with lighthearted banter.

    Jun 29, 2021·29m
  37. 37

    "All Year Sports" EP. 79

    Jun 23, 2021·26m
  38. 38

    "Watch that Fried Show" Ep. 78

    Jun 15, 2021·26m
  39. 39

    "Been in our Show Bag" Ep. 77

    Jun 8, 2021·35m
  40. 40

    "It wasn't the Real Reason" Ep. 76

    A married couple shares a lighthearted story about their kids fighting over Play-Doh on Memorial Day weekend.

    Jun 1, 2021·35m
  41. 41

    Talking Over The Mayhem Ep. 75

    May 25, 2021·24m
  42. 42

    "That's her pet peeve" Ep. 74

    May 18, 2021·32m
  43. 43

    Late but on time Ep. 73

    May 13, 2021·33m
  44. 44

    Morning Date Ep. 72

    May 4, 2021·47m
  45. 45

    "Date Night" ep. 71

    Apr 27, 2021·25m
  46. 46

    Take 2 Ep.70

    A married couple apologizes for a poor previous episode and catches up on their recent parenting struggles and life challenges.

    Apr 20, 2021·36m
  47. 47

    "Sorry for the Interruption" Ep. 70

    Apr 13, 2021·14m
  48. 48

    "Major Move" Ep. 69

    Apr 7, 2021·34m
  49. 49

    "Learning as We Go" EP 68

    Mar 23, 2021·32m
  50. 50

    "A Difficult Time" Ep. 67

    Mar 17, 2021·30m