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:
- "Getting Out of the Doghouse"—What to do if you've made a major relationship misstep, especially forgetting Valentine’s Day.
- “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
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