Vault: Is It Cheesy To Propose On Valentine's Day?

Summary

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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

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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.

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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)

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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)

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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+” |

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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.

Transcript

[A]

Get it? The bird show. Let me ask you guys a question. I want this to be more like one of those five calls, says it all type thing. But this is just for women to call in with this morning. Because over the weekend, I was hanging out with a guy that's about 23 years old, and we started talking about Bitterball, and he said he's not gonna be going because he's planning on proposing to his girlfriend on Valentine's Day. And. Right. And at first I thought, oh, how romantic. But then I remembered you guys in the back of my head going, it's a cliche day.

[B]

It is a little hallmarky.

[A]

It's a little cliche ish day. Right? Is what you guys have said in the past.

[B]

But I do have some friends who got engaged on Valentine's Day because he knew that would be the only day he could actually surprise her because it was like this. Because they typically aren't that kind of couple that would celebrate Valentine's Day or make a big deal out of it or anything like that. And it was kind of at that stage in their relationship where they had been talking about getting married for a while. They've been together a really long time. They lived together, all that kind of stuff. And he kept trying to come up with a way to surprise her and just thought that anything he planned would be. She would sort of assume. So he did it at dinner on Valentine's Day. And she was shocked. Absolutely floored. So it was like, because it was so opposite of them as a couple, it worked.

[A]

It made sense. Only because she would never see it coming.

[B]

Exactly.

[C]

I think that's unique because I think it is cliche. You don't want to. You don't want to share the anniversary of being, you know, proposed to with the. I mean, with the majority of women, if this is the only day that guys can think of to ask, you know, the girlfriends to marry him, it's just. It just seems so unoriginal, I think.

[A]

Too easy.

[C]

Yeah.

[A]

All right. 404, 741Q100. He was saying that he knows the statistics are out there. Like, 65% or 70% of women don't like the way that they were proposed to. And he's like, I don't want to be one of those guys. But I think on Valentine's Day, and he had a really romantic night, like, all planned for. But I don't know if just the day itself, excuse me, is such a cliche that it doesn't matter what you do on that day. It'll take away from it because so many others are getting proposed to on that day.

[B]

It's like he should almost do it Wednesday, like day before or something, you know, like, just to beat the cliche to the punch, I guess.

[A]

Hey, Christy, Good morning.

[D]

Good morning, Bert.

[E]

I think it's cheesy. My husband, I've always, number one, thought Valentine's Day was a Hallmark holiday. And 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.

[B]

That's a good idea.

[A]

Do you agree that the. I mean, and this guy was going to do it in front of a whole bunch of people? I think at the restaurant also. So to add to that, does. We've said before that maybe the public engagement, the public proposal doesn't work so well either?

[E]

Not on Valentine's Day. It's usually crowded, it's loud, it's not intimate. And although everybody want to think it is and it's not, I just think it's a Hallmark overrated day. And I think it. And it depends on the girl also, if she thinks it's a cheesy holiday or it's going to be a cheesy engagement.

[A]

So as a general rule, would you tell guys not to propose on Valentine's Day?

[E]

Not to propose on Valentine's Day.

[A]

All right, that's just one call there, though.

[C]

Now, is he. He plans on doing it on the 14th at dinner in front of everybody at the restaurant.

[A]

Exactly.

[C]

He may not be the only one. Like, that's the only danger there is that he's going to think he to do it and then some other guy's gonna be beat him. And you know, that's the thing, like thunder.

[A]

If you're not the first one that proposes in front of everybody, then it's really not a big deal, right?

[C]

What do you mean?

[A]

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.

[B]

Right.

[A]

Then everybody after him. It's like, now it becomes a joke.

[B]

People are rolling their eyes like, dude, I just want to eat my creme brulee.

[A]

We get it. We get it. Good morning, Sarah. You're on Q100.

[D]

Good morning, Burt Show. I do not think that it's a cheesy holiday to get proposed on. I got proposed last year on Valentine's Day, and it was such a surprise. My boyfriend and I have been going out for a very long time and he took me on a helicopter ride over Atlanta and proposed to me there.

[B]

You had to know that was coming, though.

[D]

I had no idea.

[B]

Are you sure? Are you just being nice to him for his story?

[D]

Absolutely no idea.

[B]

Okay.

[A]

I don't know, because most know, like, as soon as you got in the helicopter, you must have gone, okay, something cool is going on here, right?

[D]

No, I still. He had me going forever. The only way that I knew it was about to happen is when he started to give me this long speech about, you know, I love you and this and this and this and that. And then he pulled it out of his pocket. I was totally, totally, totally shocked.

[C]

Let me ask a question. Before he proposed to you, were you against guys proposing on Valentine's Day?

[B]

No.

[A]

You know what?

[B]

Actually.

[D]

Actually, I had it in my mind, like, he better do it. He better do it. But the night, the way the night went on, I was like, oh, well, I'm not doing. He's not doing it. He's not doing it.

[A]

I think the lesson.

[D]

It happened.

[C]

Okay.

[A]

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. The cliche. That could be the proposal on Valentine's Day.

[B]

Yeah.

[A]

Like a helicopter ride. Still pretty cool.

[B]

That's very cool.

[C]

Yeah.

[A]

Good morning, Tiffany. You're on Q100.

[D]

Good morning. My husband proposed to me on his birthday and said it was the best birthday present he could ever give himself. I think Valentine's Day is cheesy.

[B]

That's so sweet.

[A]

That's pretty good right there.

[D]

I liked it.

[A]

And you said Valentine's Day works or does not work?

[D]

Does not work for me.

[A]

It does not work for you either. Okay.

[C]

That's a great idea.

[B]

That's cute.

[A]

Good morning, Q100.

[F]

I don't think it's cheesy that my husband proposed to me on Valentine's Day and he actually did it at a restaurant, and he did it in front of everyone. 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 because we had talked about getting married, and he was like, well, I don't know when we can do it because I can't afford your engagement ring. And so I don't think it's cheesy.

[D]

I was totally surprised.

[F]

I was shocked in tears and crying. And we were both nervous as could be. So I don't think it's cheesy. I don't think it's the Hallmark holiday.

[A]

Thank you for calling.

[F]

Thank you.

[A]

All right, Melissa, now that she's gone, you can tell everybody why you rolled your eyes when she brought up the Joe Motron.

[C]

Well, I just felt like it was geared towards. I felt like it was geared toward him, you know, like, it was. He took her to a baseball complex and put it on the Jumbotron, and it just. A lot of people liked it. She cried like that.

[B]

Public engagement, like the, you know, like, announcing to the world, you know, will you marry me to this woman?

[C]

But that's a violation of what we've said before, right?

[A]

Yeah, I think just. Guys, we keep setting the bar lower and lower and lower for y', all. So, I mean, it could happen. Stuck in traffic on Spaghetti Junction right now. Most of you'd be like, this is the coolest thing ever.

[B]

He was so thoughtful.

[A]

He was so thoughtful.

[C]

I think that's what we're getting is, well, I got proposed to him Valentine's Day, and I don't think it's a Hallmark car, but you did five years ago, maybe.

[A]

Hey, Christina, you're on Q100.

[F]

Hey.

[A]

Hey.

[D]

I think it's completely cheesy. I mean, I'm all for Valentine's Day.

[E]

But 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.

[A]

So extend it, you're saying.

[B]

Spread it out.

[A]

Spread it out a little bit. You guys are making us work so hard.

[E]

I mean, come on.

[A]

Come on now.

[E]

Hey, my fiance had to do it, so I actually asked him not to.

[A]

Do on Valentine's Day, and he honored that wish.

[E]

You said he honored it, and he.

[A]

Did it on another day. There's a whole bunch of dudes listening right now that we're all set to propose on Valentine's Day and are pulling a complete U turn right now.

[B]

Or just do it early. Do it on the 13th. Or like that woman said, do it on the 15th.

[C]

But if you have everything planned, just know that there may have to be some, like, last minute change to your plan. Because if you're in that restaurant like Burt's friend and somebody else gets up and proposes, then you better just drop those plans that night and plan on it another day. Don't be the second dude to get up and propose to your girlfriend.

[A]

As soon as you sit down, even before the waiter gets there, get down on the knee. Because if you wait for appetizers, it could be too late, Right?

[B]

True.

[A]

Get it the Birch Show.