Overdue Podcast: "Sit Me Baby One More Time" Ep 05 – Dawn and the Impossible Three (The Baby-Sitters Club #5)

Podcast: Overdue (Headgum)
Date: November 22, 2025
Hosts: Andrew and Craig
Book Discussed: Dawn and the Impossible Three by Ann M. Martin (The Baby-Sitters Club #5, 1987)

Main Theme & Episode Purpose

This episode continues Andrew and Craig’s “Sit Me Baby One More Time” miniseries within Overdue, as they make their way through The Baby-Sitters Club series. Here, they dive into Book #5: Dawn and the Impossible Three, which focuses on the newly-added babysitter, Dawn, as she navigates a challenging babysitting job with the Barrett family and works through evolving club dynamics, especially with Christy. The episode’s central focus is on how the book addresses heavy family themes like divorce, single parenting, personal responsibility, and the maturing relationships among the babysitters themselves.

Key Discussion Points & Insights

1. Book Overview & Translation Titles (06:00–07:30)

• Dawn is the “newest member” and gets her own perspective in the series.
• The hosts riff on international versions of the book’s title, which all paint Mrs. Barrett (the mom) as more of the issue than her children.
  • Andrew [06:14]: “The book title leads you to believe that the kids are the problem…but mostly it’s their mom who’s the problem.”
• They highlight the book’s focus on Dawn becoming a fully realized character after being introduced in the previous book.

2. Authentic Representation of Divorce & Single Parenting (07:41–13:00)

• Both hosts discuss how three separate divorced families are central to the story.
• The book, original to 1987, carefully explores divorce without overt moralizing, instead making Mrs. Barrett’s personal chaos — not her marital status — the focus.
  • Andrew [12:25]: “It has to be structured that way…to avoid making the divorce seem like the problem and not…the specific people and personalities at play.”
• Personal reflections from the hosts about growing up with divorced parents.

3. 1980s Setting & Club Structure (09:03–10:50 and 18:31–20:49)

• The 1980s setting creates logistical child-rearing challenges (no cell phones).
• The Babysitters Club (BSC) is “drowning in calls,” and Christy continues to make big, sometimes unilateral, decisions, such as naming Dawn the “alternate officer.”
  • Andrew [19:16]: “She’s the designated survivor. She can never be at Claudia’s house just in case somebody nukes it or something.”
• Fund policies and club hierarchy are discussed humorously, highlighting Christy's authoritarian approach.

4. Plot Summary & Structure

• Dawn’s Babysitting Challenge (21:58–27:02):
  • Dawn’s first big job is babysitting the Barrett siblings: Buddy, Suzie, and Marnie.
  • Mrs. Barrett is depicted as harried, disorganized, and often absent, setting Dawn up for “impossible” conditions.
  • The kids themselves aren’t really “impossible” — it’s the lack of parental structure.
    • Andrew [27:02]: “The kids are just not being taken care of properly.”
• “Bizarre Sign” Sideplot (27:07–29:41):
  • The hosts discuss Buddy’s “bizarre sign,” a cryptic, childish insult — leading to personal stories about childhood hand gestures and minor schoolyard social dynamics.
• Club & Family Subplots (17:14, 23:53–24:49):
  • Marianne’s dad is dating Dawn’s mom; Marianne herself gets to redecorate her room and embrace new freedoms.
  • Christy is adjusting to her mom’s marriage and her own impending move, which threatens club logistics.
    • Craig [19:18]: “If the club is gone, then…if I am gone, then the club is gone. The Babysitters Club will not outlast my membership.”

5. Christy & Dawn: Friendship & Jealousy (24:49–34:08)

• Dawn perceives and navigates Christy’s jealousy surrounding best friend Marianne.
  • Craig [25:16]: “It’s a pretty mature understanding on Dawn’s part to be like, her jealousy is not something I need to fight with. It’s something I could like, try to help her with.”
• The hosts praise Dawn’s emotional maturity and the book’s nuanced depiction of changing friendships.

6. The Barrett Family: Parental Responsibility & Boundaries (30:12–43:07)

• Mrs. Barrett’s negligence becomes more apparent — no emergency numbers, poor instructions, over-reliance on Dawn.
• Dawn’s sense of responsibility pushes her to take on too much; Mrs. Barrett both complains and lavishes praise, reinforcing Dawn’s stress.
• The hosts relate this to real-world babysitting ethics: boundaries, expectations, and what’s actually appropriate for teens.

7. Climax: Missing Child Scare (43:07–50:34)

• A rainy day breaks, Buddy disappears in his Mets hat — sparking a town-wide search.
• The reality: Buddy’s dad, Mr. Barrett, picked him up by mistake to “teach a lesson” about custody — but failed to communicate, creating a panic.
  • Andrew [49:49]: “What was your plan, Mr. Barrett?...You really messed this one up.”
  • Craig [50:19]: “You made two of your children think that one of your children had been abducted.”
• Both parents’ failings are dissected; the hosts note how the 1980s context shapes community and police responses (no CPS involvement).

8. Resolution: Boundaries & Emotional Growth (53:11–54:33)

• Dawn learns to establish boundaries, telling Mrs. Barrett she can’t take on a parental role.
  • Craig quoting a Discord commenter [54:33]: “Part of taking on those responsibilities is also setting boundaries.”
• The club recognizes Mallory Pike’s competence — foreshadowing her eventual club membership.

9. Humor, Characterization & Culture (57:16–58:15)

• The hosts enjoy the recurring jokes about food differences (California tofu vs. Connecticut blandness), Dawn’s weather complaints, and Ann M. Martin’s character quirks.
  • Andrew [57:18]: parodying Christy: “If I can’t have hot dogs and mayonnaise for every meal of every day, I will pass away.”

Notable Quotes & Memorable Moments

• Andrew [06:14]: “The book title leads you to believe that the kids are a big problem…But mostly it’s their mom who's the problem.”
• Andrew [12:25]: “It has to be structured that way really carefully to avoid, like, making the divorce seem like the problem and not, like, the specific people and personalities at play.”
• Craig [19:16]: “She’s the designated survivor. She can never be at Claudia’s house just in case somebody nukes it or something.”
• Andrew [27:02]: “The kids aren’t that impossible. The kids are just not being taken care of properly.”
• Craig [25:16]: “It’s a pretty mature understanding on Dawn’s part to be like, her jealousy is not something I need to fight with. It’s something that I could like, try to help her with.”
• Craig [40:26]: “Adults certainly are hard to understand sometimes. They seem to have several faces… It’s as if they own masks.”
• Andrew [49:49]: “What was your plan, Mr. Barrett?...You really messed this one up.”
• Craig [50:19]: “You made two of your children think that one of your children had been abducted.”
• Craig [54:33]: “Part of taking on those responsibilities is also setting boundaries.”
• Andrew [57:18]: “If I can’t have hot dogs and mayonnaise for every meal of every day, I will pass away.”

Timestamps for Key Segments

• Book intro & theme discussion – 06:00
• Divorce & family themes – 07:41–13:00
• BSC Club politics & structure – 18:31–20:49
• Plot summary: Barrett babysitting – 27:02–30:52
• “Bizarre sign” childhood stories – 27:07–29:41
• Friendship, jealousy, and emotional maturity – 24:49–34:08
• Missing child plot & town response – 43:07–50:34
• Boundaries, growth, foreshadowing Mallory – 53:11–54:33
• Final jokes, food/California bits – 57:16–58:15

Tone & Style

The Overdue hosts keep their tone light and wry, mixing nostalgia with empathy and a clear-eyed literary critique. Their tangents and personal stories reflect the book’s themes of responsibility, growing up, and the quirks of childhood in the late ‘80s. They poke loving fun at both the book’s earnestness and the Babysitters Club’s proto-corporate authoritarianism, while highlighting the ways in which Ann M. Martin handles heavy topics with grace.

Overall Takeaways

• Dawn and the Impossible Three stands out for its nuanced depiction of single parenting and childhood responsibility.
• Dawn’s journey is about learning limits and boundaries, not just proving herself.
• The book’s portrayal of divorce and family upheaval feels authentic, especially for its time.
• Club dynamics are evolving, with Dawn emerging as a mature voice.
• The hosts find humor and insight in both the book’s datedness (no cell phones!) and its timeless themes (friendship, growing up, making mistakes).
• Foreshadowing for future club members, especially Mallory Pike, gets a nod.

Next episode: The series skips ahead to Book 14: Hello, Mallory! to track how the club changes as new members join and Dawn's story continues.