The Bert Show – Vault: This Guy Is Convinced These Women Are Desperate

Date: March 17, 2026
Main Theme:
The episode revisits the ongoing saga of Trey, a long-time friend of the show, who, after years of joking about not finding "the one," accepted a challenge to get married by a certain deadline. The discussion humorously and honestly explores dating pressures, cultural expectations around marriage, and the experiences of singles in their 30s and 40s—especially the stigma attached to being unmarried at a certain age. The team gets real about love, urgency, social expectations, and the madness of orchestrated relationships.

1. [01:00] Background: The Marriage Bet

• Burt resets the context—every year, Trey laments his single status, so his proactive friend Joel took matters into his own hands by booking wedding venues and rallying the show behind Trey's quest for a wife.
• Joel: "I've done everything I can, Burt. My friend's a loser." (01:48)
• The show then orchestrates dates for Trey, involving the audience and even Trey's mom, leading to an avalanche of attention and emails.

2. [02:27] The Challenge & Social Pressure

• Joel’s “marriage challenge” is both a joke and social experiment, putting real pressure on Trey to meet the deadline.
• Trey admits he’s told everyone for years “I’m getting married next year,” pushing the whole event further as an ongoing bit.

3. [03:57] Opinions on Marriage: Stigma and Skepticism

• Trey shares that being public with his quest for a spouse has led to endless unsolicited advice and jaded opinions on marriage.
  • Trey: "Every human being I've met in a public setting has given me their opinion on marriage." (03:57)
• Many people counsel him to avoid a hasty marriage, sharing their dissatisfaction with the institution.
  • Trey: “It’s amazing the amount of people that are unhappy right now in their marriage.” (04:30)

4. [04:46] Age, Singleness & Judgment

• Burt and Trey debate the stigma of being unmarried past your early 30s or 40s, revealing the assumptions people make.
  • Trey: “If I get married and divorced, and then I'm 40, 41, 45 with a divorce, I look less like a psycho than I do if I'm 40, 45, and have never been married.” (05:21)
• The group agrees similar judgments go for both men and women: there’s an ingrained societal suspicion around long-term singles.

5. [06:40] Are the 'Candidates' In It for Marriage or for Trey?

• Trey confides he feels that several of the women interested in the marriage challenge are more invested in getting married itself than in him as a person.
  • Trey: “After the second or third date, I could see these dependency issues... they just want to be married. That is their whole goal.” (12:32)
• This pattern is paralleled with stories about both genders feeling the heat to 'pair up,' especially in more traditional cultures.

6. [08:03] What Married & Single Friends Say

• Trey and Joel relay what they've heard from people:
  • Married guys in bars usually sum it up as: “You’re crazy.” (08:18)
  • Married women, and people who’ve been through the institution, want to detail their mixed or negative experiences.
  • Many reveal they’re staying together “for the kids,” or are going through the motions despite dissatisfaction.

7. [09:37] Listener Calls: The Other Side of Singleness

• Mary, a happy single woman at 43, calls in to reject the idea that being unmarried equals unhappiness.
  • Mary: “I’d rather be alone than with a horrible relationship.” (09:52)
• The hosts note that judgment still remains, regardless of personal satisfaction.

8. [10:51] The Reality of the Dating Experiment

• Despite a flood of emails, Trey only went on about two serious dates, though he met around 25 people in person (11:01).
• The experience, he admits, was “overwhelming...kind of brutal,” with most dates feeling forced or unfulfilling after initial excitement.
• Trey feels both bombarded and disillusioned with the process, leaning into recluse behavior as the experience soured him on dating.

9. [13:16] Desperation vs. Competition

• A second Mary calls with insight: “If he wants to get married that badly, you know, I bet the people that are going to contact him are the ones that are so desperate to get married.”
  • She points out that participating in such a contest may attract those more interested in “winning” or just getting married, rather than a true connection. (14:28)
• Trey concurs, breaking down the interested women into “desperate” and “competitive” types.
  • Trey: “Half the people that contacted me were desperate...the other half were competitive. It’s like The Bachelor.” (15:26)

10. [16:19] Will Trey Go Through With It? Commitment Phobia vs. A Man of His Word

• The hosts press Trey: Are you still going to get married for the sake of it?
  • Trey: “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 going to get married.” (16:19)
  • The panel advises against marrying just for the story or to check a box.
• In true Bert Show fashion, the segment closes with playful skepticism about whether Trey will actually keep his word, or if the whole episode is an elaborate running joke.

11. [17:24] Conclusion & Takeaway

• The show summarizes — Trey's mission hasn't found the magic, most potential matches seemed more eager for marriage itself than for him, and the looming “wedding” date is more a product of social pressure and radio antics than authentic romance.
• Burt: “It doesn't look like there's anybody that he's very excited about marrying, but the marriage still may be on just because he told everybody he would do it.” (17:24)

Notable Quotes & Memorable Moments

• Joel: "I've done everything I can, Burt. My friend's a loser." (01:48)
• Trey: "Every human being I've met in a public setting has given me their opinion on marriage." (03:57)
• Trey: "It’s amazing the amount of people that are unhappy right now in their marriage." (04:30)
• Trey: “If I get married and divorced...I look less like a psycho than I do if I’m 40, 45, and have never been married.” (05:21)
• Mary (caller): “I’d rather be alone than with a horrible relationship.” (09:52)
• Trey: “After the second or third date, I could see these dependency issues...they just want to be married. That is their whole goal.” (12:32)
• Trey: “Half the people that contacted me were desperate...the other half were competitive. It’s like The Bachelor.” (15:26)
• Trey: “I might still get married just to get married because I said I was going to get married.” (16:19)

Key Timestamps

• [01:00] – The history of Trey’s marriage “challenge”
• [03:57] – Trey shares how public attention changed his view on marriage
• [04:46] – Societal judgment on singles in their 30s and 40s
• [08:03] – What married & single friends really say
• [09:37] – Listener Mary calls with the single perspective
• [10:51] – Trey’s dating stats and emotional fallout
• [13:16] – Are participants desperate or competitive?
• [16:19] – Would Trey marry for the story?
• [17:24] – Final summary: no magic match (yet), just lots of social pressure

Tone and Takeaway

With characteristic self-deprecation and honesty, The Bert Show explores the absurdities and realities of modern dating and marriage. The hosts and callers bring humor, skepticism, and candid reflections to the universal questions: Does not being married mean you’ve failed? Why is there so much pressure—and what happens when you make marriage a contest? If you ever wondered what might happen if your love life became a radio bit, this episode is an entertaining, empathic answer.