The Bert Show – Vault: She Has One Target...Her Best Friend's Son!

Episode Date: April 10, 2026

Episode Overview

This candid and lively episode of The Bert Show dives into the dynamics of age-gap relationships—specifically, the sexual and emotional nuance when older women show interest in much younger men. The hosts are joined by listeners, including a 22-year-old man nicknamed "Joe the Cougar Slayer" and a woman named Bridget with a particularly tricky crush: her best friend’s son. The panel explores double standards, “sexual peaks,” and the awkward, often taboo, realities that come with crossing generational dating lines.

Key Discussion Points & Insights

1. Age Gaps & Double Standards (00:47–02:59)

• The hosts note that if the situation involved an older man pursuing a much younger woman, there likely wouldn’t be as much acceptance. However, since it's an older woman showing interest in a younger man, the conversation feels more “empowering.”
  • “If this was a 50 something year old dude going after a little 20 something year old female, I'd be like, gross, herby. But in this case, it's a woman going for a... It seems more empowering.” – Host 1 (00:52)
• The cast delves into sexual peaks:
  • For men: Early 20s (19–20).
  • For women: Early 40s and up.
  • “I think women, don't they peak in like their early 40s?” – Host 2 (01:50)
  • “A woman doesn't have confidence in her sexuality till she's in her 30s ... of course she's gonna peak higher.” – Host 1 (01:57)
• There’s exchange on whether rising sexual desire for older women is chemical or tied to confidence/freedom from shame.

2. Listener "Joe the Cougar Slayer" Joins the Show (04:09–08:57)

• Joe, a 22-year-old who suspects he is the “target” of an older woman at work (his 52-year-old subordinate), describes the situation.
  • “I've never been with anybody that old and ... I don't know how often this happens.” – Joe the Cougar Slayer (04:33)
• The group jokingly discusses men’s “mental trophy case” regarding sexual experiences:
  • “Dudes have a sort of like a mental trophy case when it comes to sex ... each and every experience that you have, you sort of put on your mental trophy case.” – Host 2 (06:29)
• Joe admits some apprehension about mixing work with pleasure, referencing bad past experiences.

3. Bridget’s Confession: Flirting with Her Best Friend’s Son (09:45–14:23)

• Bridget, a listener in her 50s, is dissatisfied with men her age and is increasingly tempted by younger admirers, especially her best friend’s 21-year-old son.
  • She recounts a provocative encounter: “I said, uh huh, keep that up and I'm gonna end up scooping you up and taking you home with me ... he just looked at me with this devilish grin and just says, I bet you could teach me something.” – Bridget (11:39)
• She is conflicted, feeling this attraction is “so wrong” due to her long-standing relationship with her friend and the boy’s age, despite them both being consenting adults.
• The conversation turns to performance concerns with older men and how sexual desire and ability fluctuate with age.

4. Panel’s Opinions and Playful Banter (12:59–14:09)

• Hosts have varying comfort levels with the topic:
  • “I'm not comfortable with this ... talking about where to pick up young boys on this Michael Jackson kind of tribute day.” – Host 3 (13:13)
• Bridget clarifies: “We're not talking young boys and our adults.” (13:21)
• The cast jokes about the “danger” of Bridget deflowering a young man:
  • “Let him lose his virginity to somebody his own age.” – Host 1 (14:21)
• Bridget reiterates she wouldn’t want to cross that line and ruin a good friendship, nor would she take a young man’s virginity.

5. Ralph Calls In: An Older Man’s Perspective (14:36–16:15)

• Ralph, 61, calls in to challenge the notion that older men can't “perform,” sharing that he and his wife maintain an active sex life.
  • “I'm 61, baby, and I'm still growing strong.” – Ralph (14:52)
  • “Everybody kept telling you where you're gonna reach your peak. ... I said, hey, dude ... it's not happening [for me].” – Ralph (15:21)
• Ralph’s account shows that sexual desire and activity can be very individual, regardless of age.

6. Advice, Reflections & Final Thoughts (16:15–16:51)

• The hosts agree that Bridget’s main issue is the scarcity of available, high-performing men her age—most are married or partnered.
• Encouragement (bordering on humorous provocation) is given for Bridget to pursue younger men—but not her best friend’s son or any virgins.
  • “Go trolling this weekend for some young guy and tell us about it on Monday!” – Host 2 (16:23)

Notable Quotes & Memorable Moments

• On Double Standards:
  “If this was a 50 something year old dude going after a little 20 something year old female, I'd be like, gross, herby.” – Host 1 (00:52)

• On Sexual Trophy Cases:
  “Dudes have a sort of like a mental trophy case when it comes to sex.” – Host 2 (06:29)

• Bridget’s Temptation:
  “I said, uh huh, keep that up and I'm gonna end up scooping you up and taking you home with me.” – Bridget (11:39)

• The Younger Man’s Perspective:
  “I've never been with anybody that old ... but she's extremely interested in me.” – Joe the Cougar Slayer (04:33)

• On Sexual Confidence:
  “A woman doesn't have confidence in her sexuality till she's in her 30s.” – Host 1 (01:57)

• On Older Men's Sexuality:
  “I'm 61, baby, and I'm still growing strong.” – Ralph (14:52)

Important Timestamps

• [00:47] – Debate on age/gender double standards begins
• [04:09] – Joe the Cougar Slayer joins, details his workplace age-gap crush
• [09:45] – Bridget’s call: admits feelings for her best friend’s son
• [12:59] – Hosts discuss the morality and awkwardness of such hookups
• [14:36] – Ralph shares that older men can still very much “perform”
• [16:23] – Hosts encourage Bridget to pursue what she wants (except her friend’s son!)

Episode Summary: Tone & Takeaways

This episode is sharp, cheeky, and frank. The Bert Show hosts skillfully balance humor ("Cougar Slayer," “mental trophy case”) with genuine exploration of the taboos and realities around older woman/younger man dynamics. Both Joe’s and Bridget’s calls bring relatable, real-world nuance to these questions. The cast acknowledges shifting desires, cultural double standards, and the unique conflict when family friendships are involved, ultimately suggesting that as long as everyone is a consenting adult and boundaries are respected—notably, not crossing the “best friend’s son” line—it’s all fair game.

For those who missed it: This episode shines for its honest talk, laugh-out-loud banter, and for giving voice to the complicated feelings around desire, age, friendship, and sex in modern dating.