The Bert Show – "Vault: Did Her Boyfriend Surprise Her With A Proposal Over The Holidays?"

January 26, 2026 | Pionaire Podcasting

Episode Overview

This episode centers on listener Sharon’s ongoing saga of hoping for a marriage proposal from her boyfriend after five years together. The cast checks in with Sharon post-holidays to find out if her boyfriend finally popped the question. The group shares empathy, humor, and candid advice as Sharon details her anticipation, letdowns, and evolving feelings. The conversation broadens into a relatable discussion about relationship timelines, expectations, and the fine art of balancing patience with self-respect.

Key Discussion Points & Insights

Setting the Scene: Sharon’s Hopeful Wait

• Sharon has called into the show multiple times with updates, each time hoping her boyfriend would propose. This episode continues the thread as the holidays (Christmas and New Year's) have just passed.
  • Burt: "It’s pretty much the same story every time we talk to Sharon. ... That makes you think, okay, this is gonna be it." (00:04)
• Sharon spots a small box under her boyfriend’s Christmas tree, convinced it’s an engagement ring.
  • Sharon: "Underneath his Christmas tree is a small box and it's a little ring box." (00:22)
  • The cast jokes about the possibility that it's jewelry, but not an engagement ring.
  • Steve: “What about earrings?”
  • Stacy: “Shut up.” (00:30)

Unwrapping the Letdown

• Sharon recounts the Christmas gift-exchange – the box contained earrings, but for his mom, not her.
  • Sharon: "It was earrings from his mom. ... It wasn't even jewelry for me." (02:12, 02:19)
  • Sharon describes the awkward moment at his parents’ house expecting a proposal, only for the box to go to his mother.
  • Sharon: "He picked up this box and he hands it to his mom. I thought I was gonna die." (03:08)
• Presents from her boyfriend are met with indifference – Sharon only had eyes for the (mom’s) earring box.
  • Jeff: “She didn’t even try them on.” (03:51)
  • Sharon: “I don’t know, some crappy sweater, I don't know. Not really.” (04:34)

Reflecting on Relationship Timelines

• After feeling repeatedly let down, Sharon sets a mental deadline of Valentine’s Day to get serious about her future.
  • Sharon: "If it doesn't happen by then, because I have to get serious." (05:18)
• Jen relates, having gone through the same anticipation with her own husband:
  • Jen: "Once you've been dating for that long ... you're ready for them to propose. You're ready to take that next step in your life, and they're just not on the same page." (01:07)
• The group discusses the emotional difficulty of repeatedly psyching oneself up for an engagement that doesn’t happen.
  • Burt: “That’s the thing that Jen was saying was so dangerous about this whole scenario, is that you can’t reboot your attitude.” (05:43)
    • Jen: “It’s hard and it’s disappointing, and there’s nothing you can do.” (06:13)

Listeners Chime In: Advice and Tough Love

• Stacy, a caller, gives blunt advice about not “giving the milk away for free”:
  • Stacy: "Why buy the cow when you can get the milk for free? ... Baby girl, you've got to seriously move on." (06:37)
• Burt and the team explore how best to express one’s feelings without pressuring a partner:
  • Burt: “Stacy gave me an ultimatum ... So the ultimatum worked in my case.” (08:11)
  • Jeff: “It was when we were going to a friend's wedding, and she just pointed out the number of weddings of people that we have been to ... since we started dating together.” (08:58)

The Gender Divide and Internal Deadlines

• Steve notes men and women often perceive marriage differently, with men seeing it as the end of freedom and women viewing it as the beginning of a dream realized.
  • Steve: “Weddings and guys and proposals is not something they're looking forward to. ... Guys are a little slower to getting it done.” (09:43)
• Burt strongly advocates for personal boundaries and secret deadlines:
  • Burt: "Set a date in your own head. And if he makes it, great ... and if not, then it's time to move on." (10:09)
• Other listeners call in to echo the advice, sharing how setting an internal (or external) deadline shifted their mindset – and sometimes their relationships.
  • Stacy (caller): "I gave him a deadline and not really told him that this is your ultimatum. ... I got so disgusted ... I was like, I don't care if we get married. I'm getting myself ready to be single again." (10:49)
• Stacy also offers an amusing “stench” theory: when you truly stop caring, the desperation “stink” goes away, and that shift can actually prompt change in the partner.
  • Stacy: "As my husband likes to say, the stench will be off of you. ... Then he'll realize what he has and you'll be married." (12:14)
  • Burt/Jeff: "Stench of desperation. ... Not even a smell or a whiff. A stench like the rotting flesh of a roadkill raccoon." (12:51, 12:56)

Sharon’s Final Word

• Sharon sets a concrete timeline for herself:
  • Sharon: “I give them till Valentine’s Day, and then I’m … I’m taking my toothbrush out of the house.” (13:13)
• The group wishes her luck and promises to check in after Valentine’s Day.
  • Burt: "That's a start, right? All right, we'll talk to you soon." (13:19)

Notable Quotes & Memorable Moments

• "You can't reboot your attitude."
  — Burt, reflecting on the difficulty of shutting off hope once it starts (05:43)
• "Why buy the cow when you can get the milk for free?"
  — Stacy (caller), giving tough love to Sharon (06:37)
• "The stench will be off of you."
  — Stacy (caller), on how true emotional detachment changes relationship dynamics (12:14)
• "Set a date in your own head. And if he makes it, great... and if not, then it’s time to move on."
  — Burt, on personal boundaries and self-respect (10:09)
• "I give them till Valentine’s Day, and then I’m taking my toothbrush out of the house."
  — Sharon, drawing her own line in the sand (13:13)

Key Timestamps

• 00:22 — Sharon suspects boyfriend's small box is a ring
• 02:12 — Discovery: the box was earrings for his mom
• 03:08–03:37 — Sharon describes painfully watching the gift go to his mom
• 04:45 — The repeated letdowns across holidays (Christmas, New Year’s)
• 05:18 — Sharon sets a Valentine's Day deadline
• 06:37 — Stacy's "Why buy the cow..." advice
• 08:11 — Stories of how hosts handled or received ultimatums/deadlines
• 10:09 — Burt advocates secret personal deadline strategy
• 12:14 — Stacy's “stench will be off you” metaphor
• 13:13 — Sharon: “Valentine’s Day or I’m moving out” final declaration

Episode Tone & Takeaways

The episode is a classic Bert Show blend of humor, empathy, and straight talk. Listeners will find camaraderie and laughter in the cast and callers’ stories, but also receive hard-earned wisdom on the importance of knowing your worth and setting boundaries in long-term relationships. Sharon’s experience is both an entertaining saga and a springboard for a broader, honest conversation about love, timing, and self-respect.