The Bert Show – “Vault: Her Birthday Proposal Plan Hits Another Snag”

Date: March 18, 2026
Participants: Bert (host), co-hosts (including possible Jen or Megan McCardell), Kimberly (caller/guest)

Episode Overview

In this episode, the Bert Show revisits a listener’s ongoing relationship dilemma: Kimberly’s plan to propose to her boyfriend on his birthday, after previous failed attempts, and the complexities surrounding their mismatched desires for marriage. The Bert Show team dives into the nuances of relationship expectations, personal boundaries, and the risks of pushing a partner to commit.

Key Discussion Points & Insights

1. Recap of Kimberly’s Journey

• Kimberly’s Initial Plan: Originally, Kimberly wanted to propose to her boyfriend on Christmas but was thwarted when he found out in advance and asked her not to do it (01:30–02:06).
• Her Certainty: “I really feel with 100% certainty that he's gonna say yes. He's the love of my life.” – Kimberly (01:36)
• The Boundary: The boyfriend had clearly stated he was not ready for marriage and was not the marrying type, but Kimberly was still hopeful (01:30–02:46).

2. The Birthday Proposal Attempt

• Setting the Scene: Kimberly described a perfect birthday: brunch, shopping, a homemade dinner, and wine. She planned to propose with a “man engagement ring,” emphasizing her seriousness (03:55–05:01).
• Interrupted Again: As she tried to present the ring, her boyfriend pre-empted her:
  “He saw me going in the cabinet, and I turned around and he's like, stop. If you are going to do what I think you're going to do, don't do it.” – Kimberly (05:07)
• Boyfriend’s Reasoning: He reiterated he loved her and wanted to be together, but wasn’t ready for marriage:
  “I'm not saying never. I’m just not ready to get married right now.” – Kimberly, paraphrasing her boyfriend (06:12)

3. Panel Reaction: Is She Pushing Too Hard?

• The panel debates Kimberly’s persistence versus respecting her boyfriend’s boundary:

  • “The relationship is sort of going that way naturally. Why are you pushing it?” – Bert (07:24)
  • “If this is your line in the sand, then you have to stick to it.” – Co-host, possibly Jen or Megan (08:10)

• Kimberly clarifies she’s seeking a next level of commitment, not just a wedding:

  • “It’s not that I want to change him. … I just want to be married to him.” (07:02)

4. Personal Timelines and Expectations

• Setting Boundaries: Co-hosts stress the need for Kimberly to enforce her standards, suggesting if she wants commitment after two years, she must act accordingly if it's not met (08:10–08:40).
• Kimberly’s Line:
  “If we're engaged by, you know, by the time I'm 28…” – Kimberly (12:11)
• Discussion on how relationship timetables and boundaries help avoid later resentment (08:41–09:43).

5. Promise Rings and Commitment Symbols

• On Promise Rings: The role and definition of promise rings versus engagement rings is discussed, with some lighthearted teasing among the hosts (09:12–10:12).

6. Listener Call-In and Outside Perspectives

• Listener ‘Ronnie’ Weighs In:
  “I think this girl is pushing it to the limit, that this guy just gonna leave.” – Ronnie (13:24)
• Hosts and Kimberly discuss outside opinions and how others perceive her commitment level.

7. Kimberly’s Resolution

• Pulling Back: Kimberly agrees (reluctantly) to stop proposing, stating she’ll wait another two years and, if nothing changes, re-evaluate the relationship (13:42–14:14).
  • “I'm not gonna ask him again. I mean, I'm gonna wait. I'm gonna give him, like another two years, and then I have to do what I have to do...” – Kimberly (13:42)

Notable Quotes & Memorable Moments

• On Knowing When to Let Go:
  “Are you ready to cut yourself loose and allow this guy to take off based on your timetable? Are you sacrificing too much of yourself right now?” – Bert (10:36)

• On Changing for a Partner:
  “He told her straight up, that’s just not for me. … But that was before she came along, so it feels like it’s different.” – Bert (03:39–03:45)

• On Relationship Labels:
  “You’re tired of being called a girlfriend.” – Co-host (09:27)

• On Emily’s Honesty:
  “I think that she's not being completely honest when she says it's two years. I think she wants it now…” – Co-host (11:46)

Timestamps for Key Segments

• 01:26–02:46: Recap of Kimberly’s proposal history and boyfriend’s initial rejection.
• 03:55–05:21: Kimberly’s birthday proposal story and boyfriend shutting it down.
• 07:24–08:40: Panel questions Kimberly’s urgency and discusses relationship pacing.
• 08:40–09:43: Boundaries, standards, and the “line in the sand” discussion.
• 09:12–10:12: Promise rings and what labels mean in relationships.
• 13:24–13:42: Listener Ronnie’s call and the “desperation” debate.
• 13:42–14:14: Kimberly’s closing resolution on waiting another two years.

Tone and Language

The episode blends empathy for Kimberly’s perspective with sharp wit and trademark Bert Show banter—light teasing, honest advice, and candid conversations. The panel oscillates between supportive advice and gentle ribbing, keeping the tone both real and entertaining.

Summary Conclusion

Kimberly’s saga highlights the challenges when personal relationship timelines clash. The Bert Show crew encourages honesty with oneself and partners, the importance of boundaries, and self-respect—reminding listeners that moving at one’s own pace is crucial, but a relationship should never come at the cost of one’s personal standards or happiness. For Kimberly, the episode ends with her committing to pause her proposals, giving both herself and her boyfriend space—at least for two more years.