The Bert Show – Full Show PT 3: Tuesday, March 17 [Vault]

Date: March 17, 2026
Cast: Bert, Kristin, Abby, Cassie, Tommy, Joel, Trey, Jeff, Wendy, Melissa
(Episode content starts at 01:42, skipping ads and non-content)

Episode Overview

This episode centers around a lively, candid discussion on relationships, marriage, and the sometimes comical, sometimes sobering realities of dating in adulthood. The show dives into Trey's ongoing (and increasingly questionable) quest to get married, explores the social pressures of being single, and shares the team’s superficial New Year's resolutions, peppered with humor and listener call-ins.

Key Discussion Points & Insights

1. Trey’s Marriage “Challenge”

(01:42–18:25)

• Background:
  Trey annually claims he'll get married but never does, prompting his best friend Joel to take matters into his own hands by reserving hotel rooms and sending out save-the-dates for a supposed wedding (02:14–03:07).
• Radio Involvement:
  The Bert Show amplified Trey's challenge by bringing it to the airwaves—which led to a wave of date candidates and even involvement from Trey's mom (03:44–03:47).
• Outcome So Far:
  • Despite opportunities, Trey remains uncommitted, not currently in love, and only loosely entertains the idea of marrying for the challenge (04:08–04:30).
  • Trey's reflections: "Every human being I've met in a public setting has given me their opinion on marriage ... I'm a little jaded about the whole concept of marriage." (Trey, 04:36–05:04)
• Social Pressures and Stigma:
  The discussion shifts to societal perceptions—both men and women face suspicion if still unmarried in their 30s, 40s, or beyond.
  • "Why does it have to be that there's something wrong with you?" (Burt, 05:29–06:01)
  • "If you're a man who's in your mid-40s or near 50 and you've never been married, a woman's gonna look at you ... women will judge you for that." (Melissa, 06:38–06:50)
• Dating Experiences:
  Trey only went on two actual dates out of a wave of emails, found many participants “dependent,” and grew skeptical of their motives:
  • "Some of the girls that I met ... after the second or third date, I could see these dependency issues ... are they really into me, or are they just into this whole concept?" (Trey, 13:12–13:56)

Notable Quote:

“I wouldn’t bet that I’m getting married to somebody I love. I might still get married just to get married, because I said I was gonna get married.”
– Trey (16:59)

2. Listener Call-Ins & Marriage Perceptions

(10:17–16:23)

• Caller Perspective:
  A 43-year-old single woman calls in, sharing she's “happy by myself” (10:19–10:36), underlining that many prefer solitude over unsuitable partnerships.
• Stigma Discussion:
  The show debates whether singles in their 30s/40s lie about being divorced to dodge judgment (11:04–11:12).
• Matchmaking Pressure:
  Friends often try to couple up single friends, even when they're content solo (11:13–11:31).

Notable Quote:

“I’d rather be alone than with a horrible relationship.”
– Caller Arlene (10:32)

3. Superficial New Year’s Resolutions

(20:33–30:43)

• Bert: Wants to finally catch a marlin after years of failed attempts (20:33–22:45).
• Wendy: Hopes to date an NFL player (even if it's just the cousin of one) and sit in the family section during a game (24:39–25:33).
• Melissa: Lands a voiceover gig in a video game thanks to her radio visibility (23:05–23:37).
• Jeff: Seeks to be a contestant on a game show—and win, preferably a tangible prize (23:41–24:23).
• Joel: Aims to play an entire round of decent golf (22:45–22:58).

Memorable Moment:

When Wendy shares she was contacted on MySpace by a hopeful NFL Combine recruit and plans to meet up with him—potentially fulfilling her resolution in January:

“Ooh, Destiny, this is fun ... So we exchanged a couple emails ... We will be hanging out tonight.”
– Wendy (27:17–28:01)

Notable Quotes & Moments (with Timestamps)

• On Marriage Jadedness:

  "It's amazing the amount of people that are unhappy right now in their marriage." (Trey, 05:11)

• On Social Judgment:

  "If you’ve tried it once and you failed, all of a sudden you have more credibility." (Burt, 06:50)

• On Blind Dating Burnout:

  “You go on one of these and you meet and then you talk for an hour ... it just drags and drags ... it was kind of brutal.” (Trey, 12:09–12:38)

• Listener Skepticism:

  “If he wants to get married that badly, [the women who contact him] are not anybody you would really want to be in a relationship with anyway. So that kind of turned me off ... I just don’t want to make a bad decision or wrong choice again.” (Caller Mary, 14:22–16:00)

• On Competition Among Dates:

  “Half the people that contacted me were desperate ... but the other half were competitive. Literally, the girls were like, I have to win this thing regardless of what it is.” (Trey, 16:06–16:23)

• On Goal Setting and Lowering the Bar:

  “Sometimes you go for the quarterback. The other time you just get the punter or the long snapper.” (Wendy, 30:35)

Segment Timestamps

• 01:42–18:25: Trey's Marriage Challenge, listener perspectives, and marriage skepticism.
• 18:25–20:33: Ad break (skipped).
• 20:33–30:43: Cast shares superficial New Year's Resolutions; Wendy’s NFL dating quest.

Tone and Style

The episode’s tone is unabashedly humorous, honest, and self-deprecating, with the hosts routinely poking fun at themselves and each other. The discussions, especially those about marriage and dating, blend candid reflection with sarcasm, keeping the episode both insightful and entertaining.

Final Thoughts

For anyone who feels the pressure to settle down—or is just tired of awkward blind dates—this episode is both relatable and cathartic. The Bert Show continues to shine for its authenticity and wit in tackling the highs and lows of adult relationships and life’s lighter challenges.