The Bert Show Podcast Summary

Episode: Vault: Is It Cheesy To Propose On Valentine's Day?
Date: January 27, 2026
Main Host(s): Bert, Kristin, Abby, Cassie, Tommy & The Bert Show Cast

Episode Overview

This episode explores the divisive question: Is it cheesy to propose on Valentine’s Day? The Bert Show team invites primarily women to weigh in with their perspectives—drawing from personal experiences, opinions on public proposals, and thoughts about originality versus tradition. Listeners call in with their stories and verdicts, leading to a lively and often humorous examination of romance, surprise, cliches, and expectations.

Key Discussion Points and Insights

1. The Valentine’s Day Engagement Debate

• Bert’s Prompt (00:00): Bert kicks off with a scenario about a young man planning to propose to his girlfriend on February 14th, questioning whether it’s romantic or just predictable and “Hallmark-y.”
• Panel Opinions:
  • Most of the team initially leans toward “cliche,” citing the sense that Valentine’s Day proposals lack originality and might blur together with other couples doing the same thing.
  • There’s acknowledgment that, for some, the element of surprise can outweigh the cliché—especially if the couple isn’t typically into Valentine’s traditions.

“It is a little hallmarky.” — Kristin (00:30)
“It made sense. Only because she would never see it coming.” — Bert (01:16)

2. Listener Call-Ins: Real-Life Proposals

Christy’s Story (02:15)

• Proposal Date: Feb. 15th—not Valentine’s Day—“in front of all my family.” Total surprise, best possible outcome for her.
• View on Feb. 14th: Opposed to Valentine’s Day proposals, finding the day “overrated” and “not intimate” in public settings.

“My husband surprised me on the 15th instead of the 14th in front of all of my family. And I thought it was the best thing, and I was totally surprised.” — Christy (02:17)

Sarah’s Helicopter Proposal (03:49)

• Proposal Date: Valentine’s Day, on a helicopter ride over Atlanta. Absolute surprise, loved the experience.
• Panel’s Skepticism: The team jokes she must have anticipated it with such a big event, but Sarah insists she had “absolutely no idea.”
• On Being Against 2/14 Proposals: She wasn’t opposed beforehand, and the unique scenario won her over.

“I got proposed last year on Valentine's Day, and it was such a surprise… I was totally, totally, totally shocked.” — Sarah (03:49–04:27)

Tiffany’s Story (05:18)

• Proposal Date: On her husband’s birthday; “the best birthday present he could ever give himself.” Admits she finds Valentine’s Day cheesy.

“I think Valentine's Day is cheesy.” — Tiffany (05:18)

Baseball Jumbotron Proposal (05:41)

• Scenario: Another caller describes her husband proposing at a restaurant in front of everyone, with the proposal on a stadium Jumbotron.
• Reaction: Emotional, shocked, and completely happy; doesn’t find it cheesy.

“We went to a restaurant at a baseball complex, and he put it on the big Jumbotron. And everyone looked, and I was totally surprised… I don't think it's cheesy.” — Listener (05:41–06:08)

Christina & Alternative Celebration (07:02)

• Christina argues for separating the engagement from the holiday: “Do it on a different day where we get two holidays.”
• She convinced her fiancé not to propose on Valentine’s Day.

“That's the one day of the year that we can actually, you know, expect something nice. Do it on a different day where we get two holidays.” — Christina (07:10)

3. Public Proposals: Love Them or Hate Them?

• The cast and callers echo skepticism about public proposals—especially on busy holidays—since it can reduce intimacy or feel performative.

“It's usually crowded, it's loud, it's not intimate... It depends on the girl also, if she thinks it's a cheesy holiday or it's going to be a cheesy engagement.” — Christy (02:47)

• The hosts joke about multiple proposals in the same restaurant on Valentine’s Day: being the “second” or “third” guy to propose can make it feel less special, even laughable.

"If you're the second or the third or the fourth guy that proposes in the restaurant, it's a big deal for the first guy that proposes. Then everybody after him... now it becomes a joke." — Bert (03:33–03:39) "People are rolling their eyes like, dude, I just want to eat my creme brulee." — Kristin (03:41)

4. The Takeaway: Know Your Partner & Make It Meaningful

• There’s consensus that whether a Valentine’s Day proposal works depends on the personalities involved. If it’s unique or deeply meaningful for the couple, it can work—even offsetting the cliche.
• Several suggest choosing a different day to “spread out” the celebrations and keep the engagement special.

“I think the lesson you could learn here is that if you're going to do it on Valentine's Day, it's got to be so over the top that it offsets... the cliche.” — Bert (05:04) “Just know that there may have to be some, like, last-minute change to your plan.” — Cassie (07:52)

Notable Quotes & Memorable Moments

• Kristin: “It is a little hallmarky.” (00:30)
• Bert: “If you're not the first one that proposes in front of everybody, then it's really not a big deal, right?” (03:27)
• Kristin: “People are rolling their eyes like, dude, I just want to eat my creme brulee.” (03:41)
• Bert: “So as a general rule, would you tell guys not to propose on Valentine’s Day?” (03:03)
• Christy: “Not to propose on Valentine’s Day.” (03:08)
• Cassie: “Do it on a different day where we get two holidays.” (07:10)
• General Advice: “If you wait for appetizers, it could be too late, right?” — Bert on timing public proposals (08:09)

Timestamp Guide to Important Segments

| Timestamp | Segment | Highlights | |-----------|---------------------------------------------|--------------------------------------------------------| | 00:00 | Episode introduction & setup | Valentine’s Day proposal scenario posed | | 02:15 | Christy’s call | Surprise proposal on Feb 15, anti-2/14 stance | | 03:49 | Sarah’s helicopter proposal | Pro-Valentine’s proposal via unique, memorable event | | 05:18 | Tiffany’s birthday proposal | Unique date > Valentine’s Day, personal meaning | | 05:41 | Restaurant/Jumbotron proposal | Major public proposal, strong emotional response | | 07:02 | Christina’s alternative view | Arguing for separate engagement and Valentine’s Day | | 07:52 | Planning pitfalls & advice | Be ready to adapt plans on crowded nights | | 08:09 | Final thoughts | Timing is everything; avoid being “proposal number 2+” |

Final Thoughts

The episode’s lively debate and first-person stories paint a nuanced picture: While Valentine’s Day proposals are often seen as cheesy or overdone, exceptions abound—especially when the event is truly surprising, customized, or resonates with the couple’s unique story. The main advice? Know your partner and don’t be afraid to personalize your special moment, even if that means breaking with Hallmark tradition.