The Bert Show – Full Show PT 3: Wednesday, December 31 [Vault]

Air Date: December 31, 2025
Host: Bert and The Bert Show Cast (Kristin, Abby, Cassie, Tommy, and others)

Overview

This episode of The Bert Show spotlights the fun, drama, and real-life mishaps that relationships face, focusing on two main segments:

1. "Getting Out of the Doghouse"—What to do if you've made a major relationship misstep, especially forgetting Valentine’s Day.
2. “Idiot’s Guide to Marriage Proposals”—Advice on how not to mess up a proposal, with hilarious and cringe-worthy real stories.
   The show wraps with a jaw-dropping challenge where listeners call in with stories of the worst partners they've ever known. Throughout, the cast maintains a candid, humorous, and at times deeply empathetic tone.

Key Segments & Insights

1. How to Get Out of the Doghouse After Forgetting Valentine’s Day

Timestamps: 00:39 – 14:53

Main Discussion Points:

• Many men woke up “in the doghouse” for forgetting Valentine’s Day, and the cast crowdsources advice for how to recover.
• Listeners and hosts share personal stories of being forgotten or slighted on special days.
• The consensus is that making up for it is rarely a one-day fix—genuine remorse and effort are mandatory.

Steps & Tips for "Getting Out of the Doghouse":

• Grovel—a lot.

  "Grovel, grovel, grovel, grovel until you can't do it anymore."
  —Jen Hobby (03:12)

• Do something selfless, with no benefit for yourself.
• Absorb criticism; don’t make excuses.

  "Don't say why you couldn't do it. Just be honest and go, ‘I am a moron.’ Totally authentic apology."
  —Bert (10:29)

• Avoid big, after-the-fact gifts like jewelry.

  "A handwritten note on notebook paper that says the right thing goes a lot further than a diamond ring the next day."
  —Jen Hobby (06:01)

• Double down on the next occasion—make it even more special ("You'd better hope her birthday is February 16th!" —Bert, 07:37).
• Show public acts of love.
• Plan a big future event (like a trip) and build up to it.
• Send daily apologies (e.g., flowers with messages over a week).

  "Consistent groveling."
  —Kristin (13:53)

Notable Quotes:

• “Is forgetting Valentine's Day that big of a deal?”
  “Absolutely.”
  —Bert & Cassie (03:19)
• “You just did something in total disregard of your girlfriend.”
  —Cassie (03:37)

Memorable Moments:

• Jen recalls her own experience being forgotten on Valentine’s: “I was ready to break up with him.” (02:11)
• Hilarious impressions of frustrated significant others. (04:20)

Listener Calls:

• Multiple listeners echo that fast fixes don’t work, and genuine, sustained effort is needed (07:02–14:15).

2. Idiot’s Guide to Marriage Proposals

Timestamps: 15:02 – 29:50

Main Discussion Points:

• Staggering stat: 8 in 10 women are unhappy with their proposal story (15:04).
• Cast and callers share both “bad” and heartfelt proposal stories.
• Listeners help create a list of proposal dos and don'ts.

Rules for a Memorable Proposal:

• Make it personal and sentimental.

  “Just make it something special that she's told you in the past. Listen and connect it.”
  —Bert & Kristin (21:14)

• Do it in private (not at a party or in front of family).
• Have a real ring (not a bar straw).
• Pre-plan the proposal (don’t just wing it).
• Get down on one knee.

  “Take a knee, for sure.”
  —Kristin (23:29)

• Ask the actual question.

  “Four words have to be included... Will you marry me?”
  —Kristin (25:07)

• Pick a date significant to your relationship (not necessarily Valentine’s Day).
• If possible, ask her dad or a parent for permission.

  “Now that I look back at it... I’m sorry I robbed him of that. Only happens once.”
  —Bert (27:20)

• Never piggyback on someone else's occasion (graduation, birthday, etc.).
• Put in visible effort—sentiment beats extravagance.

Notable Quotes:

• "The wedding is the bride's time. The proposal is the groom's time. This is your time to shine."
  —Cassie (19:15)
• “If the proposal is boring, you can pretty much suggest that the sex life is going to be boring.”
  —Kim (26:12)

Memorable Moments:

• A listener’s proposal with pawn shop rings engraved with someone else’s name (19:23).
• Bad proposal stories include using proposals as last-minute birthday gifts and proposing with makeshift rings in bars (18:48, 22:21).

3. The Most Evil Partners—Listener Competition for “Worst Husband/Boyfriend Ever”

Timestamps: 30:01 – 44:44

Main Discussion Points:

• Bert details the “most evil guy in the world.” (CIA lies, affairs, absent for wife’s cancer walk, neglectful dad).
• Listeners attempt to “top” the story with their own:

Highlights:

• A cheating husband who lied about being in the CIA, abandoned his wife at her cancer walk, and missed his child’s life (30:01–36:18).
• Callers recount men who left pregnant wives, lied about cancer, ran elaborate scams with multiple women, and engaged in criminal acts (36:47–43:48).

Notable Quotes:

• "How does somebody like that face themselves in the mirror every morning?"
  —Kristin (36:18)
• “Lying about cancer. I’m so sorry that we have so many people in the competition.”
  —Cassie (41:50)

Memorable Moments:

• Genuine shock and empathy from the Bert Show cast as listeners reveal heartbreaking and outrageous stories.
• Listeners and hosts collectively marvel at the capacity for deception and cruelty in relationships.

Standout Quotes by Timestamp

• “I was ready to break up with him.”
  —Jen Hobby on her husband forgetting Valentine's Day (02:11)
• “You have to do something completely selfless.”
  —Cassie (04:04)
• “Eight in ten women are not happy with the way their men are proposing marriage to them.”
  —Bert (15:04)
• “This is your time to shine.”
  —Cassie, on proposals (19:15)
• “Four words have to be included in your proposal. Will. You. Marry. Me.”
  —Kristin (25:07)
• “If the proposal is boring, you can pretty much suggest that the sex life is going to be boring and unimaginative.”
  —Kim (26:12)
• “How does somebody like that wake up every day?”
  —Kristin (36:18)

Episode Flow & Tone

The episode skillfully balances playful banter, authenticity, and occasional shock, moving from light-hearted relationship tips to sobering real-life drama. The cast’s vulnerability and wit encourage listeners to share candidly, deepening the sense of community and catharsis. If you’ve ever fumbled a romantic day, wondered how not to propose, or questioned if your relationship is truly “that bad”—this episode serves laughs, lessons, and plenty of jaw-dropping moments.

Quick Reference – Timestamps

• 00:39 – 14:53: How to escape the “doghouse” (Valentine’s Day mishaps)
• 15:02 – 29:50: How to propose (including horror stories and dos/don’ts)
• 30:01 – 44:44: Worst partners—unbelievable listener stories