The Bert Show — "Vault: Do You Regret Having A Second Child?"

Date: January 16, 2026
Host: Bert and The Bert Show Cast (Kristin, Abby, Cassie, Tommy, plus callers)
Main Theme:
A candid, real, and humorous discussion about whether parents ever truly regret having a second child, the personal and relational challenges involved, and the deep emotions parents experience when making family size decisions.

Episode Overview

This episode centers around co-host Bill's personal dilemma: whether he and his partner Stacy should have a second child. Stacy’s difficult first pregnancy, their son's early birth, and current family dynamics fuel a lively roundtable with listeners calling in to share their perspectives on growing a family. The hosts openly discuss the emotional complexities, societal expectations, and real-life challenges (and joys) tied to adding another child to the household.

Key Discussion Points & Insights

1. Bill’s Family Planning Struggle (00:02–03:31)

• Bill shares his longing for a second child but notes Stacy’s hesitancy due to her difficult first pregnancy and concerns over time and emotional demands.
  • "Everything he [Hayden] does to me is just so fun and so funny, and I have found more love in my heart over the last two and a half years than I even knew I had in me." (00:24)
  • Major tension: The fear of inviting more hardship versus the regret of never having tried.

2. Parent Regret: Myth or Reality? (00:50–03:31)

• Bill references advice from friends: Most don’t regret having a second child, but many regret not having one.
  • "I've never met anybody that regretted having that second child." (01:35)

3. Sibling Perspective & The Value of Companionship (03:31–04:54)

• Caller 1 confidently advocates for siblings, emphasizing the unique bond and lifelong companionship.
  • "It’s a relationship like none other in my life… I would want that for my children." (03:36)
• Christy and the group jokingly note siblings' ability to "compare notes" about their parents, lightening the conversation.

4. Honest Parental Experiences: The Challenging Second Child (05:01–06:14)

• Caller 2 admits her second child was far more challenging than the first, while expressing deep love and no regret.
  • "Had we had her first, there would never have been a second." (05:07)
  • "She was a difficult baby… but had she been born first, we just wouldn’t have done the second." (05:25)
• Highlights the unpredictability of each child’s temperament, and its impact on family dynamics.

5. Changing Family Dynamics and Strain (06:29–08:32)

• Bill discusses fears of a challenging child upending the family balance, referencing stories of “hell children” placing a strain on relationships.
  • He observes that these decisions are revisited anxiously before each child.
  • Host: "It's almost as if parents have this… stress over the decision to have a child, which you should because it's a huge decision." (06:42)

6. Expanding Beyond Two: The "Outnumbering" Phenomenon (07:07–08:05)

• Bill (Caller): Adds a comic note, stating he regrets the third child, not the second.
  • "Once the kids outnumber the parents, it's a losing battle." (07:18)
  • Encourages having at least a second, arguing that multiple children reveal the uniqueness in each one.

7. Personal Philosophies & Birth Order (08:05–08:58)

• Christy discusses how second children often develop divergent personalities, which can be both challenging and healthy for independence and household balance.

8. Special Needs & Strained Relationships (09:13–10:47)

• Jessica: Brutally honest about her special needs child, highlighting the increased strain on a marriage and daily life.
  • "I would not give him back for the world. But it is extremely hard to have a special needs child." (09:29)
• Bill expresses empathy, noting the visible strain on families dealing with such challenges.

9. Blended Families & Retrospective Honesty (11:11–11:57)

• Caller 3: Shares the unique challenge of having an “extra” child much younger than their siblings, candidly admitting some regret:
  • "I would not take a million dollars for him, but I wouldn't give a nickel for another one." (11:42)

Notable Quotes & Memorable Moments

• Bill: "Every time he does something really cool or we have a moment, I say to Stacy, how can we not want to do this again? This is so awesome." (00:27)

• Caller 1: “...the special relationship [with my brother]... I would want that for my children.” (03:36)

• Caller 2: “Had we had her first, there would never have been a second.” (05:07)

• Jessica: “I would not give him back for the world. But it is extremely hard to have a special needs child.” (09:29)

• Caller 3: “I would not take a million dollars for him, but I wouldn't give a nickel for another one.” (11:42)

Noteworthy Timestamps for Important Segments

• 00:02: Bill introduces his family planning dilemma
• 01:35: Bill reflects on the lack of regret among parents with a second child
• 03:31: Caller 1's heartfelt sibling testimonial
• 05:07: Caller 2’s honest account of a challenging second child
• 07:18: Bill (Caller) regrets the third child, not the second
• 09:29: Jessica shares on special needs and family strain
• 11:42: Caller 3’s humorous and real blended family perspective

Tone and Style

In classic Bert Show fashion, this episode maintains a mix of candor, humor, and heartfelt reflection. The hosts and callers keep the conversation lively, real, and sometimes self-deprecating, ensuring the discussion is accessible and resonant for anyone who's pondered growing their family.

Summary Takeaway

The episode offers a nuanced, multi-faceted view on the question, “Do you regret having a second child?” While the answer is almost universally “no,” the truth is layered: second (or third) children bring both unexpected joy and unique challenges. The journey isn’t easy, and the decision requires soul-searching—but, as the show’s guests and hosts reveal, the love shared in a growing family can outweigh the hardest moments.