The Bert Show – Vault: “She’s Worried About The Shirt Her Son’s Wearing to School”

Date: November 11, 2025
Hosts: The Bert Show Cast, featuring Crystal (Caller, Mom), Steve (Assistant Principal), Tara (Licensed Social Worker), Mandy (Caller), Kim (School Counselor), and others.

Episode Overview

This episode dives into a heartfelt, funny, and at times contentious dilemma from Crystal, a mom facing her son’s insistence on wearing his sparkly “Princess” T-shirt (a hand-me-down from his older sister) for his first day of kindergarten. The hosts, alongside expert and listener call-ins, explore questions of parental authority, childhood self-expression, gender norms, and practical “first day” anxieties. The episode brings together diverse perspectives — from parental instinct, school administration, child psychology, and “let kids be kids” advocates — in The Bert Show’s trademark candid, humorous style.

Key Discussion Points & Insights

1. Background: The Dilemma (01:03–04:44)

• Crystal’s 5-year-old son wants to wear his favorite shirt — a black, sparkly, “Princess” T-shirt from his big sister — for the first day of kindergarten.
• Crystal feels uncomfortable with this. Her husband thinks it’s “no big deal.”
• Crystal: “He sleeps in it... I think it’s the spark. He likes the black with the sparkles... He doesn’t know what it says. Obviously he can’t read. But to me, I just… I don’t want my son going to his first day of school with a T shirt that says Princess.” (02:57–03:19)
• The hosts gently rib Crystal about how emotional these “first day” rituals can get for parents.

2. What’s Really the Issue? (04:46–05:11)

• The hosts press Crystal about why she’s upset.
• Co-host: "I guess I want to know your underlying issue with the word princess. Like, what are we really talking about here?" (04:46)
• Crystal: “Well, it’s for a girl. Exactly. And he’s a boy.” (04:53)

3. School Perspective – Warnings about First Impressions (05:26–08:24)

• Steve, Assistant Principal, calls in:
  • “First impressions are very important. It’s not so much the kids you’re gonna have to worry about, it’s the faculty, it’s the staff. The parent is sending their child, a male student, to school with a princess shirt on… That really can set up some things for later on, perception wise.” (05:30–05:50)
  • Steve argues that kids can be “labeled” by peers and teachers, and these impressions can stick.
  • “It’s very easy for everyone to judge... then that’s going to be talk of the school the rest of the day.” (06:06)
  • Suggests parents should “control what their child wears at school.” (07:49)

4. Child Psychology/Social Work Insight – It’s About Security (09:13–10:23)

• Tara, Licensed Social Worker, weighs in:
  • “...It’s security. And we are talking about, this is a big day... that might make him feel more comfortable in a really new situation.” (09:27–09:37)
  • Tara suggests compromise: shirt could be kept in his backpack or used as a comfort object, but not worn.
  • “Give him an option but not taking away maybe what makes him feel the most comfortable.” (10:14–10:23)

5. Compromises and Creative Parenting (10:28–11:10)

• Mandy (parent caller): Proposes layering — let him wear the “princess” shirt, but cover with a button-down.
  • “I’m gonna pick out a shirt that you wear over it... so it’s almost like a layered type look.” (10:42–11:03)
  • Hosts joke about how layered clothing might look even weirder.

6. Husband vs. Wife Viewpoint (12:16–13:14)

• Crystal recaps: Her husband “couldn’t even care about the issue whatsoever. He really thinks I’m making such a big deal about it.” (13:40)
• Hosts share anecdotes about their own “make it disappear” approach to kids’ odd attachments, comparing Crystal’s son's T-shirt to baby dolls and beloved toys.

7. “Let Him Be!” vs. “Protect Your Kid” (14:27–21:48)

Let Him Wear It:

• Multiple callers and co-hosts argue that kids need some freedom to express themselves.
• Caller: “Let him wear whatever he wants.” (14:34)
• Caller: “Not making it that hard for him. You're giving him a lesson… approve the fact that he is his own person and can make his own decision.” (15:49)
• Another caller: “He's going to get teased about more things than wearing a princess shirt the first day of school. That's life.” (15:36)

No, Redirect:

• Kim, School Counselor:
  • “He will forever be that child who wore the pink shirt on the first day of school. These kids grow up together and stay together. And… it sounds so silly that something like that can stigmatize them, but it really, really can.” (16:53–17:15)
  • Advocates for redirecting kids to a new, special shirt “Kids can be redirected very easily.” (17:38)

On Parenting Authority:

• Co-host: “You’re the parent and you can steer the child in certain directions... I think you have to say at times I’m the parent and what I say goes… this may be your line in the sand on that.” (21:08–21:48)

8. Long-Term Worries vs. Is it Really a Big Deal? (20:13–22:31)

• Host makes the case that elementary memories can “haunt” kids in middle and high school via yearbooks and photos:
  • “All it’s going to take is somebody looking through their pictures… especially if he is one of the less popular kids that is going to come back to haunt him.” (20:13–21:08)
• Final caller: “To me it’s just… too overdramatic. I just, I mean, I guess as a parent… I just think… you’re making too much of a big deal about it.” (22:11–22:31)

Notable Quotes & Moments

• Crystal: “He sleeps in it… he doesn’t know what it says.” (02:57)
• Steve (Assistant Principal): “First impressions are very important. And it’s not so much the kids you’re gonna have to worry about, it’s the faculty, it’s the staff.” (05:30)
• Tara (Social Worker): “It's security... give him an option but not taking away maybe what makes him feel most comfortable.” (09:27–10:23)
• Kim (Counselor): “He will forever be that child who wore the pink shirt…” (16:53)
• Caller: “Let him wear what he wants — that’s life!” (15:36)
• Host (summarizing): “Right down the middle. Glad to help.” (22:31)

Important Timestamps

• 01:03 – Crystal’s call and outlining the T-shirt dilemma
• 02:23 – The shirt’s origins and Crystal’s discomfort explained
• 05:30 – Steve (Assistant Principal) weighs in: first impressions at school
• 09:13 – Tara (Social Worker) on the importance of security objects for young children
• 10:28 – Mandy provides a compromise (layering shirts)
• 14:27 – Debate intensifies on the seriousness and implications
• 16:53 – Kim (School Counselor) on the long-term impact of “standout” moments in early school years
• 21:08 – Co-host on picking your “parental authority” battles
• 22:31 – Closing remarks: Crystal, uncertain, thanks the hosts and listeners

Takeaways

• The dilemma bridges the personal (a child’s attachment and comfort), the social (gender norms, peer judgment), and the parental (navigating authority and compassion).
• The show offers a humorous, real-parent take — admitting that sometimes, even with all the debate, there isn’t a “one size fits all” answer. Many listeners and hosts wind up split on whether to let the boy wear his beloved shirt or redirect him for his own protection.
• The conversation highlights the mixture of anxiety, love, and second-guessing that comes with modern parenting — all in a relatable, sometimes laugh-out-loud morning radio style.

For those weighing a similar parenting challenge: You’re not alone, and, as The Bert Show proves—sometimes the debate is the real answer!