Podcast Summary: The Bert Show

Episode: Vault: We Attempt To Help A Listener Find A Date For her High School Reunion
Release Date: January 23, 2026
Host: The Bert Show Cast (Bert, Kristin, Abby, Cassie, Tommy, et al.)
Theme: Helping a listener, "Emma," find the perfect one-night date for a high-pressure high school wedding/reunion event.

Episode Overview

This episode centers around Emma, a listener facing the daunting prospect of attending a high school friend’s wedding—doubling as an unofficial reunion—as the only single guest. The Bert Show team mobilizes their audience, specifically seeking self-proclaimed matchmaking experts, to help Emma find an ideal date who can convincingly play her perfect boyfriend for one memorable night. The cast hilariously debates “boyfriend for hire” qualifications, the expectations Emma has, and how to keep things discreet, with the conversation underscored by real-talk, supportive advice, and the signature Bert Show humor.

Key Discussion Points and Insights

1. The Matchmaker Call-Out

[00:00–00:52]

• The cast appeals to their listener base for people with a knack for matchmaking, specifically those with a track record of successful couple setups.
  • A: "If you brag that there are five couples in your circle and you put them all together..." (00:32)

2. Emma’s Dilemma

[01:08–03:06]

• Emma joins the call, explaining her predicament: She’s the only single person attending a high school friend's wedding, which will also serve as a reunion.
• Several factors heighten the pressure:
  • A catty small-school atmosphere, where people will gossip if she arrives solo.
  • At least three now-married ex-boyfriends will be present.
  • Emma wants to look "impressive," meaning a charming, attractive, and socially adept escort.
  • A: "No less than three now married ex-boyfriends will be attending. Oh, so she is in need of someone to play the role of her boyfriend who is completely perfect. No pressure, though." (02:37)

3. Qualities of the Ideal Date

[03:06–04:48]

• The group distills what makes the perfect plus-one:
  • Charm and likability trumps looks or wealth.
  • The candidate should easily converse with anyone and handle social situations smoothly.
  • Emma prefers to meet and prep with the date beforehand to make their "relationship" believable, but not too elaborate.
  • Responsibility is key—no drunken shenanigans, please.
  • B: "I think that's more key than what he looks like...If it's somebody who can walk into a room and make friends quickly...that's exactly who you want." (03:25)
  • D (Emma): "I would like to be comfortable with each other and then say that we've known each other for a little." (04:08)
  • D (Emma): "I don't want to take somebody to a wedding with an open bar and be that guy in the middle of the dance floor..." (04:36)

4. Learning About Emma

[04:55–05:17]

• Emma’s brief intro:
  • Grew up in Atlanta, passionate about her job, enjoys live music and comedy, high school in Atlanta.
  • The show briefly jokes about small-world encounters and the risks of the date being a former classmate.

5. The Logistics & the Offer

[05:39–06:39]

• The wedding is just over a week away, so there's a tight turnaround for matchmaking.
• Compensation? Emma offers a trade: the selected date gets a night in which she'll be his designated driver for him and friends—“a night for a night.”
  • D (Emma): “Something in Atlanta that I would love is a DD for a night…so I thought that might be a good [trade]." (05:49)
  • A: "That's a night for a night." (06:08)

6. Laying Down the Ground Rules

[06:39–07:22]

• The team clarifies expectations: The date must convincingly play the boyfriend role, stay in character, and avoid revealing the arrangement.
• The show will post Emma's info for potential matchmakers and resume the story after the weekend.
  • A: "…then the matchmakers…will start scouring Atlanta to find the perfect guy… and then we can bring you together on the air on Monday morning." (06:59)

7. Q&A from Listeners

[07:55–09:14]

• Listener "Maria" (misnamed Kathy at first) calls in with a concern: Won’t Emma's high school friends figure out it's her from the radio?
  • The team reassures her: "Emma" is a pseudonym.
    • B: "Well, we did change her name." (08:29)
• Listener Kathy offers up a potential candidate but queries the acceptable age range.
  • The team promises to get clarity and pass along ages to matchmakers.

Notable Quotes & Memorable Moments

• On the pressure of being the last single guest:
  • A: "Reading from her email, it says this particular wedding is the epitome of every single woman's nightmare." (02:01)
• On preferring personality over looks:
  • B: "I think that's more key than what he looks like…somebody who can walk into a room and make friends quickly…" (03:25)
• Summary of responsibilities for the plus-one:
  • D (Emma): "I don't want to take somebody to a wedding with an open bar and be that guy in the middle of the dance floor..." (04:36)
• Exchange about discretion:
  • B: "Important that, like, the guy obviously can't get hammered and tell anybody the truth..." (06:39)

Timeline of Important Segments

| Timestamp | Segment Description | |-----------|------------------------------------------------------------| | 00:00 | Call for listeners with matchmaking experience | | 01:08 | Emma describes her predicament and the stakes | | 03:06 | Team and Emma specify ideal qualities for the plus-one | | 04:55 | Emma shares personal interests and background | | 05:39 | Logistics, trade offer (Emma offers to be DD for a night) | | 06:39 | Rules for date, prepping for the matchmaking process | | 07:55 | Listener calls: identity exposure concern, age question |

Episode Tone and Takeaways

True to The Bert Show’s style, the episode mixes genuine empathy for Emma’s situation with quick wit, lively banter, and interactive engagement from listeners. The conversation navigates the stakes of high school reunions, the social politics of being single at milestone events, and the lengths people will go for a bit of social protection, all while keeping things light and fun.

Conclusion

The show wraps up with Emma on hold, the team preparing to post for matchmaking volunteers, and listeners chiming in with both leads and concerns. The ultimate solution is to reconvene with Emma after the weekend, hopeful that a real-life fairy godparent will emerge from Atlanta’s matchmaking scene in time for her “night to remember.”