The Bert Show – Full Show Pt 2: Monday, January 26 [Vault]

Date: January 26, 2026
Hosts/Cast: Bert, Kristin, Abby, Cassie, Tommy, Melissa, Jen, Nicole
Podcast Theme: The Bert Show delivers a blend of authentic, humorous, and real-life conversations. This episode focuses on messy relationships, heartbreak, roommate drama, expectations around engagement, and the nuances of gift-giving in relationships.

Episode Overview

This episode of The Bert Show dives into the emotional turmoil of romantic entanglements: a caller debating “revenge” on her boyfriend after he rekindles a toxic relationship with his ex, ongoing anticipation of proposals and relationship milestones, and a lighthearted analysis of what holiday gifts indicate about the health of couples. Listeners call in with their own stories and perspectives, leading to thoughtful, funny, and sometimes biting debates among the cast.

Segment 1: Should I Send Revenge Pics of My Cheating Boyfriend?

Timestamps: 00:00 – 14:17

Key Discussion Points

• Michelle calls in, heartbroken after her boyfriend (who she took in post-breakup with his ex) goes back to the same ex.
• Michelle discovers evidence: a graphic photo of her boyfriend and his ex sent directly to her with a mocking message.
• Michelle’s dilemma: Should she send the picture to his friends, family, or even co-workers as revenge?
• The cast splits: Melissa advises the high road, while Jen plays the devil’s advocate for “send it all out.”
• Listeners call in with passionate perspectives, creating a heated moral debate about blame, respect, revenge, and closure.

Notable Quotes & Moments

• Host 2: “So it could be infidelity we’re talking about.” [00:24]
• Michelle: “I want to send this picture to everyone we know. I am just so beside myself.” [05:00]
• Melissa (high road): “Any action in the heat of passion is the wrong thing to do… Be the better person.” [06:36]
• Jen (low road): “I say go ahead and send it out to everybody… Give him a dose of his own medicine.” [07:05]
• Nicole (caller): “Karma is a son of a gun, and it will come back to him. Trust me, sweetie, you don’t need to do anything.” [07:27–08:03]
• Host 2: “Yes, she might have brought this on herself, but the way that he handled the breakup part of it was so malicious and so aimed to be hurtful…” [08:04]
• Chaz (caller): “I didn’t send them out, but I posted them on MySpace and Facebook… I wish, looking back on it, that I didn’t do that.” [13:14–13:38]

Insights

• Core debate revolves around the ethics and consequences of revenge in the face of betrayal.
• Several listeners caution against rash digital revenge, citing potential legal and emotional fallout.
• Significant focus on the distinction between being told there’s “no commitment” and assuming exclusivity due to romantic/roommate arrangements.
• The cast provides both emotional support and humor, while listeners offer hard-won perspectives from their own relationship disasters.

Segment 2: The Never-Ending Wait for a Proposal (Sharon’s Story)

Timestamps: 14:22 – 27:43

Key Discussion Points

• Sharon’s ongoing saga: Five-year relationship, waiting anxiously for a proposal—sees a “ring-sized” box under the Christmas tree, only to discover it’s earrings for his mom.
• The emotional rollercoaster of anticipating special moments and repeatedly getting let down.
• Cast reflects on the “deadline dilemma”—how long should someone wait for a proposal before moving on?
• Listeners and hosts share their own stories of ultimatums, deadlines, and communication breakdowns.

Notable Quotes & Moments

• Sharon: “He has a Christmas tree at his place, and underneath is a little ring box. I think it’s gonna be on Christmas…” [14:43–15:22]
• Jen: “Once you’ve been dating for that long… You’re ready for them to propose, you’re ready to take that next step, and they are just not on the same page.” [15:27]
• Melissa: “Men are almost taught this is the end of their freedom, where women are kind of groomed to dream about the day they’ll get married.” [24:03]
• Host 2: “I really do think that it’s a smart idea to have a deadline day in your head… If not, it’s time to move on.” [24:30]
• Nicole (caller): “Another mother sticker getting them free for five years…” [21:11]
• Sharon: “I give him till Valentine’s Day, and then I’m taking my toothbrush out of the house.” [27:34]

Insights

• The anxiety and disappointment of waiting for commitment resonates with listeners and the hosts, sparking a stream of advice both practical and humorous.
• Gender perspectives on marriage timelines and “ultimatums” are explored.
• Sharon’s story becomes a touchstone for similar experiences among the team and callers.

Segment 3: Gift-Giving Forensics: What Your Christmas Present Says About Your Relationship

Timestamps: 27:48 – 38:05

Key Discussion Points

• An email prompts a conversation about whether thoughtful (or thoughtless) holiday gifts predict the future of relationships.
• The Bert Show opens the “phone lines” for listeners’ stories about what they received for Christmas, then “diagnoses” relationship prospects.
• Themes include gift imbalance, misalignment of thoughtfulness, and what certain presents (or lack thereof) say about a couple’s stability.

Notable Quotes & Moments

• Host 1: “If he gives you four $20 shirts and two DVDs, and you shopped since November… that relationship’s over, inside of 90 days!” [28:25; 29:40]
• Melissa: “We set a $50 limit, but Katie Jo traded in old jewelry to get me diamond earrings for $50. She totally outdid me.” [30:23–31:26]
• Jessica (caller): “Two shirts, two pairs of pants and some costume jewelry… I got him an ipod.” [32:09–32:17]
• Host 1: “Not only did he try, he also thinks you have a little ass. You’re good. Congratulations.” [32:58]
• Angela (caller): “I got nothing. Not even a card… We’re married.” [37:03–37:17]
• Host 1: “I think you’re gonna get a late Christmas present. It’s gonna be divorce papers!” [37:47]

Insights

• The team pokes fun at the “science” of matchmaking according to gifting habits, with a consensus that a lack of thoughtfulness signals trouble.
• Multiple stories prove that it’s not about the gift’s cost, but its meaning and effort.
• “Getting nothing” for Christmas, especially in a marriage, is universally declared as a red flag.

Memorable Moments and Tone

• The Bert Show’s signature candid, relatable, and comedic style shines, whether offering tough love, playing devil’s advocate, or poking fun at their own experiences.
• Live caller interactions introduce real-world messiness and humor, infusing the show with unpredictability.
• Standout punchlines like “Karma is a son of a gun…”, “Don’t send the pictures—it’s never the right move,” and “You can’t reboot your attitude” showcase the show’s blend of empathy and sharp wit.

Timestamps for Key Segments

| Segment | Start | End | |--------------------------------------------------------|----------|----------| | Revenge Photos Drama (Michelle) | 00:00 | 14:17 | | Proposal Anticipation (Sharon) | 14:22 | 27:43 | | Holiday Gift “Diagnostics” | 27:48 | 38:05 |

Summary Takeaway

This episode delivers a rollercoaster of relationship drama: from the reckless impulse for revenge to the slow agony of proposal anticipation, to the playful “gift-ology” of holiday presents. The Bert Show’s cast and callers provide raw honesty, hard-won advice, sardonic observations, and plenty of laughs for anyone who’s ever loved—and lost, waited—and worried, or wondered if that thoughtless present is the beginning of the end.

New listeners will find a tight-knit cast, high audience engagement, and a commitment to “real talk” about real-life messes—served with humor and heart.