The Bert Show – Vault: Is There A Proper Way To Blackmail?!
Podcast: The Bert Show
Host: Pionaire Podcasting
Episode Date: January 5, 2026
Episode Overview
The Bert Show cast dives into the ethics and realities of blackmail, spurred by personal experience with sharing party photos and requests to remove them. The hosts open up the phone lines for real-life blackmail stories from listeners, leading to a mix of humorous takes and sobering reflections on how blackmail plays out in everyday life. The conversation is peppered with the show’s signature blend of humor, candor, and empathy.
Key Discussion Points & Insights
1. The Photo Scandal — Personal Stories Kick Off the Topic
- Jeff shares how he innocently uploaded party photos from a recent night out, only to receive multiple calls demanding their removal due to embarrassing or incriminating content.
- Melissa volunteers that she was one of the people who asked for photos to be taken down because she was embarrassed by an unflattering picture of a lump on her head.
- Discussion about how even harmless photos can spiral into potentially blackmail-worthy situations.
Quote:
“So I just, you know, I took him down. I'm not out to get anyone or anything, but I started to think this is how blackmail begins.”
— Jeff (05:25)
2. Is There a Right Way to Blackmail?
- The cast wonders aloud about real-life blackmail: Is it just a movie trope, or does it actually happen to regular people?
- Rodney Ho jokes about blackmailing friends for the website link but quickly turns the situation into a broader discussion about morality.
Quote:
“So anyways, so there's, you know, like, that's how blackmail begins. So if this ever occurs again... I fully intend on having the camera. Because pictures are cool.”
— Jeff (06:02)
- Melissa encourages listeners to call in if they’ve experienced blackmail, promising anonymity via a voice disguiser.
“If you've ever been in any kind of blackmail, you were the one doing the blackmailing. You got blackmailed. You knew of somebody. Want to know if this happens in real life? Real People, time...”
— Melissa (07:59)
3. Listener Blackmail Stories
Story 1: Blackmailed for Sexual Favors
(08:16–12:28)
- A female caller shares that after drunkenly keying a man’s car, she was caught on surveillance. Instead of pressing charges, the man blackmailed her into repeated sexual acts to keep quiet.
- She moves cities, changes her number, and is still pestered by the blackmailer.
- The cast is shocked and sympathetic, urging her to wait out the statute of limitations and asserting she “wouldn’t even get a ticket” for the original crime.
Quote:
“I was shown doing an act of vandalism, but I never heard back. But then he started calling... and would demand sexual favors to keep it quiet. Oh, no.”
— Caller (08:21)
Quote:
“At this point, it's very much worth it for me just to pay.”
— Caller (11:03)
Story 2: Roommate Revenge and Coerced Hookup
(13:06–15:28)
- Another caller recounts a college roommate blackmailing her after a spring break hook-up while she was engaged. The roommate forces her to go on a trip and have sex with her cousin, threatening to reveal her secret if she refuses. Decades later, the threat still hangs over her.
Quote:
“She wanted me to hook up with her cousin... she had this over me and she kept saying, I'm going to take you on this trip to Louisiana, and if you don't go, I'm going to tell.”
— Caller (13:49)
Story 3: Ex-Boyfriend Threatens with Tape
(15:39–17:17)
- A caller describes how her parents threatened to cut her off over her boyfriend. When her boyfriend found out, he threatened to send a sex tape to her parents if she broke up with him.
- She ultimately breaks into his apartment with help from a friend and steals the tape, hoping it was the only copy.
Quote:
“He said if I did not, If I stopped seeing him, if we broke it off, that he was going to send my parents the tape.”
— Caller (16:40)
4. Reflection on Blackmail in Everyday Life
- The hosts are surprised at the prevalence and seriousness of real blackmail stories from listeners.
- Jokingly, Jeff claims he doesn’t need trench coats and manila envelopes to blackmail but maybe needs a cousin in Louisiana (17:33).
- The group underscores the emotional and ethical toll of blackmail, despite their usual light-hearted banter.
Quote:
“You know what? Remember that when you have stress in your life, at least there's not a chance that someone's gonna send a tape of you having sex with someone to your mom and dad.”
— Jeff (17:00)
Notable Quotes & Memorable Moments
- “It's almost like what happens at Vision stays at Vision. And you were putting it on the Internet.” — Bert (04:38)
- “So if anybody calls with a blackmail story, we can put them on the Voice.” — Jessica (07:55)
- “There's nothing worse than having your parents think, well, first of all, they hated him anyway. And then for them to know that you're having sex and then to actually see it. There's nothing worse I can think of.” — Caller (17:17)
Timestamps for Key Segments
- 01:32 – Jeff opens the blackmail theme with the party photos anecdote.
- 04:38 – Bert raises the ‘what happens at Vision stays at Vision’ rule.
- 06:02 – Jeff considers the temptation and ethics of blackmail.
- 07:59 – Invitation to listeners for blackmail stories—lines open.
- 08:16–12:28 – First caller: blackmailed for sexual favors after vandalism.
- 13:06–15:28 – Second caller: coerced into a hookup by a blackmailing roommate.
- 15:39–17:17 – Third caller: ex-boyfriend threatens with a sex tape.
- 17:00 – Jeff closes with a reflection on life and blackmail stress.
Final Thoughts
Despite starting with laughs about embarrassing party photos, the episode delves into the shocking reality of blackmail in listeners' lives. The discussion balances humor, empathy, and ethical pondering, making for a strikingly memorable show that underscores how secrets—and their leverage—can deeply affect everyday people.
Recommended for listeners who enjoy candid, real-talk explorations of moral dilemmas, peppered with humor and authentic storytelling.