The Bert Show – Vault: Massey's New 20 Year-Old Virgin Date

Release Date: November 7, 2025
Host: Jamie Massey with Jeff, Melissa, Caitlyn, plus listener call-ins
Podcast: The Bert Show, Pionaire Podcasting

Episode Overview

This episode centers on Jamie Massey’s latest dating adventure: going out with a younger guy—a 20-year-old virgin. The cast dives deep into the age gap, dating motivations, taboos, and societal double standards, all in the show's trademark spirited, bantering tone. Lively debates arise about what's "icky," what counts as a deal-breaker, and how personal and cultural values shape approaches to relationships—particularly when sex and age are involved.

Key Discussion Points & Insights

1. Jamie’s Dating Track Record & The Premise

• Jamie Massey recounts her dysfunctional dating history:
  • “We have told you before that the history of Jamie Massey's dating life is not sad. It's laughable.” (Jamie, 01:00)
  • Past issues: men revealing they’re married mid-date, guys ditching her with the check, etc.
• Jamie tries “something new” by dating a younger man, after previous attempts at dating older or married men haven’t worked out.

2. The Age Difference Debate (28 vs. 20)

• Jamie reveals she’s 28, dating a 20-year-old she met through friends.
• The cast jokes about the generational gap:
  • “You were walking in the Seafire side of the Caribbean and he was there to see cars.” (Jamie, 02:10)
  • “She was going to an R rated movie and he wanted to sneak in on her ID.” (Jeff, 02:15)
• Is it different if an older woman dates a younger man?
  • Caitlyn: “If I'm icked out by a 28 year old guy chasing after a 20 year old girl, then I can't be different if it's a 28 year old woman and a 20 year old guy.” (03:31)
  • Jeff points out an “ickiness” scale: “You're borderline icky… it's like a piece of chicken that's just raw still. Like in the very middle.” (04:11)

The "Icky Factor" Mathematical Formula

• Melissa introduces the “half your age plus seven” formula:
  • “The icky formula is what? Take half of your age, which is 20. Plus seven.” (04:00)
  • Calculated as 14+7=21; at 20, he’s one year below Jamie’s “minimum.”

3. Motivations & Double Standards

• Discussion about why older women date younger men:
  • “Let's be honest, there's one reason why you go out with a guy that's young. It's because he's good looking.” (Jamie, 05:19)
• Jokes about lessons learned and casting Jamie as a "predator" (in jest).

4. The Bombshell: He’s a Virgin (Saving Himself for Marriage)

• Jamie reveals her date is saving himself for marriage:
  • “He. I've. You say, but I don't want to say because I would look like—” (Jamie, 05:55)
  • “Is he a virgin?” (Jeff, 05:59)
  • “Yes.” (Jamie, 06:00)
  • “Are you going to deflower him?” (Jeff, 06:01)
  • “No.” (Jamie, 06:03)
• Jamie struggles with dating but not being able to have sex:
  • “If you're sexually frustrated now, wouldn't you rather be sexually frustrated alone rather than this hot piece of 20 year old meat in front of you that you can't do anything with?” (Jamie, 06:11)
• Jeff jokes about “high school stuff”:
  • “He can still do the old high school stuff… touch you above your bra, the dirty paint, pant rub, all those things.” (Jeff, 06:33)

5. The “V Bomb” Aftermath & Perspectives

• The cast interrogates Jamie about how the topic arose; Jamie explains it came up in casual religious conversation.
  • “He said, yeah, by the way, I'm saving myself for marriage. And I was like, saving what?” (Jamie, 07:46)
• Jamie reflects on the pressure of possibly being “the one” who changes his vow:
  • “I could not do that because… if he filled guilty about it, he would resent me for the rest of his life.” (Jamie, 09:06)
• Cast asks Jamie if she’ll still date him or “dump” him.
  • “Don’t I turn into like a complete—if all of a sudden I’m like, won’t date him anymore because he doesn’t do that?” (Jamie, 09:32)

6. Listeners Call In: Real-Life Experiences

• Dolores shares her story:
  • She married a 23-year-old who was a virgin when they met; he was also 20 when they started dating.
  • Overcame religious reasons eventually; no guilt involved.
    • “It was one of those where I had been married… he just said that, you know, he really had never found someone… who made him say, you know, yeah, I’m willing to go that far.” (Dolores, 11:15)
• Dolores’ advice: “Don't do it. Let somebody else be the person to take it from him, but don't do it.” (Dolores, 12:42)
  • Jamie: “Yeah, no, I don't want to be that person. That's too much pressure.” (Jamie, 12:48)

7. Final Thoughts: Should She Continue or Let Go?

• A second caller advises moving on:

  • “Let that go real quick. Honey, run in the other direction and find you another 20. 21, 2019, for God's sakes. But get you some ass and get it quick.” (Dolores, 14:23)

• Jamie seems undecided about whether to break up:

  • “I mean it's, it's not even to the breakup dumping point, you know…” (Jamie, 14:48)

8. Notable Quotes & Jokes

• On the age gap:
  • “28 and 20, he's very mature.” (Jamie, 04:05)
  • “Did you take him to the Disney store?” (Melissa, 04:42)
• On sexual tension:
  • “He's denying you that based on the Bible.” (Jamie, 13:39)
• On coping:
  • “If you've learned nothing from listening to the Burt Show today, I'll remember that last night.” (Melissa, 14:38)
  • “Go get you some hats and get it quick.” (Dolores, 14:42)

Timestamps for Key Segments

• Jamie Explains Her Dating Past & Younger Guy Reveal:
  01:00–02:35

• Debating the Age Gap, “Icky” Formula, and Double Standards:
  03:00–05:00

• Virgin Reveal, Jamie’s Dilemma, and Banter on Sexual Tension:
  05:38–09:06

• Listener Dolores Shares a Similar Experience:
  10:50–12:39

• Callers Advise Jamie (Should She Drop Him?):
  13:31–14:46

Memorable Moments & Quotes

• On the “Icky Formula”:

  • “So you're in the icky factor.” (Melissa, 13:14)

• On self-awareness:

  • “I cannot be the one to do that. Because, like, say he was. Felt guilty about it. He would resent me for the rest of his life.” (Jamie, 09:06)

• On learning from others:

  • “Don't do it. Let somebody else be the person to take it from him, but don't do it.” (Dolores, 12:42)

• Banter Highlight:

  • “Go get you some ass and get it quick.” (Dolores, 14:32)

Summary

This episode captures the Bert Show’s honest and irreverent approach to taboo dating situations, focusing on Jamie Massey’s new flame: a much younger, deeply principled (and very attractive) 20-year-old virgin. The panel’s laughter, teasing, and sincerity turn a potentially awkward topic into an entertaining and relatable exploration of age, sex, values, and the complexities women face in the dating world.

Listeners leave with:

• Food for thought on age gaps and double standards
• Firsthand accounts of handling sexual boundaries
• Plenty of laughs, sharp one-liners, and Jamie’s relatable journey to figure out what she wants

Essential takeaway:
While the group offers plenty of ribbing, they ultimately respect Jamie's decision—highlighting that it’s okay for dating to be a process, even if it’s not the fairytale ending we expect.