The Bert Show: Vault — "What Not To Ask Your Current Boyfriend"

Date: November 7, 2025
Cast: Bert, Kristin, Abby, Cassie, Tommy, Producer Tracy, and callers Lauren, Cynthia, Nathan
Main Theme:
This episode revolves around the minefield of “dangerous questions” in relationships: things you should absolutely never ask your current boyfriend, girlfriend, spouse, or partner. The Bert Show cast and listeners contribute to an evolving, lighthearted but honesty-fueled list of these no-win curiosity traps.

Key Discussion Points & Insights

Why We Ask Dangerous Questions (01:40–02:49)

• Bert introduces the topic by confessing to asking his wife, Stacy, a question he knew he didn’t want the answer to: “If I wasn’t around, which ex-boyfriend would you have ended up with?”
  • Quote (Bert, 02:10): “For her, it’s a no win because I’m not going to be happy with the answer. I don’t even really want to know the answer. So why do you even ask?”
• The cast jokes about the name “Glenn,” Stacy’s answer (with playful banter about mustaches and small penises).

The Classic Traps: Numbers & Ex-Comparisons (03:16–04:27)

• Never ask:

  • “How many people have you slept with?”
  • “Am I the best you’ve ever been with?”
  • “Who was the best?”

• The cast discusses how these questions usually lead to insecurity, jealousy, and the temptation to ask further comparison questions.

• Quote (Kristin, 04:18): “You don’t wanna go down that road… You open the door of ‘how many people,’ then that gate is open and all sorts of things can escape.”

Digging Up the Past (04:40–05:25)

• Bert and the cast expand the list:
  • “Which of my friends would you date if I wasn’t around?”
  • “What’s your least favorite body part about me?”
• Bert shares how he was “trapped” by Melissa into admitting his least-favorite thing about his wife (on air).

Listener Call-Ins: Real-Life Regrets (05:16–07:40)

• Lauren: Never ask if your partner has slept with any of your friends. She says if you know it might haunt you, better not to know.
  • Real tension: Some cast members would rather know (to avoid being “the fool”), while others want the bliss of ignorance.
• Cynthia: Made the mistake of asking her boyfriend what his exes looked like—regretted triggering unhealthy comparisons.
  • Quote (Cynthia, 07:05): “In my head… I think of some homely looking girl that is 10 times worse than I am just to kind of boost my self esteem a little bit. But if I ask… I go against everything I thought and I don’t want to know that… but my curiosity just kills me.”

The Spiral of Insecurity (07:31–08:02)

• The cast cautions against leading questions like:
  • “Who had better [body part]?”
  • “What’s the wildest thing you did with your ex in bed?”
  • These are almost guaranteed to have answers that hurt or haunt you.

Morbid Hypotheticals & Extreme Scenarios (08:26–10:46)

• Producer Tracy’s additions:

  • “If I died, how long would you wait to start dating again?”
  • “If I died, who would you be with?”
  • “If we broke up, how long before you started seeing someone else?”

• Nathan (caller):

  • “Would you still love me if I became a quadriplegic?”

• The team jokes about physical caretaking (e.g., “Would you wipe my ass if both my arms were broken?”), mixing honest reflections with irreverent humor.

• Quote (Cassie, 10:36): “In this situation, are you financially well off to hire a caretaker to wipe the butt?”

When Even the Honest Answer Doesn't Help (08:59–09:29)

• Pro Vita (caller): Shares the futility of asking, “Was that person better than me?”—no one tells the truth, and even if they did, no good can come of the answer.
  • Quote (Pro Vita, 09:18): “Don’t ask a question because I don’t think people will really honestly answer it.”

The Ex Factor (09:29–09:41)

• All agree: Most disastrous questions relate to partners’ exes.
  • Quote (Cassie, 09:29): “Every single one we’ve written down has to do with the ex. That’s what causes problems in these questions.”

Notable Quotes & Moments

• Bert (02:10): “For her, it’s a no win because I’m not going to be happy with the answer. I don’t even really want to know the answer. So why do you even ask?”
• Kristin (04:18): “You don’t wanna go down that road… You open the door of ‘how many people,’ then that gate is open and all sorts of things can escape.”
• Cynthia (07:05): “In my head… I think of some homely looking girl that is 10 times worse than I am just to kind of boost my self esteem a little bit. But if I ask… I go against everything I thought and I don’t want to know that…but my curiosity just kills me.”
• Cassie (10:36): “In this situation, are you financially well off to hire a caretaker to wipe the butt?”
• Pro Vita (09:18): “Don’t ask a question because I don’t think people will really honestly answer it.”

Timestamps for Important Segments

• Main topic intro: 01:40
• Bert’s Europe story & ex-boyfriend question: 01:57–02:49
• Opening the floodgates with “How many people?” 03:16–04:27
• Comparison questions (“Am I the best?”): 04:15–04:27
• Listeners Call-In: Lauren on friends and exes: 05:16–06:31
• Cynthia on asking about exes’ looks: 06:51–07:40
• Wildest ex stories in bed: 07:52–08:02
• Producer Tracy’s morbid hypotheticals: 08:26–08:38
• Physical caretaking scenarios: 09:46–11:40

Takeaways & Tone

• Tone: Playful, self-deprecating, and honest—with humor used to take the edge off uncomfortable truths.
• Key Message:
  Certain questions in relationships serve no constructive purpose and are usually asked out of insecurity or morbid curiosity. Most revolve around exes, comparisons, and extreme “what ifs.” The show encourages self-restraint and healthy boundaries for the sake of your own—and your partner’s—emotional well-being.
• Final Word:
  If you know the answer won’t help (or could only do harm), it’s best not to ask.