Vault: She had a first date on Valentines Day

Summary

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Episode Overview

Episode Title: Vault: She had a first date on Valentine's Day
Podcast: The Bert Show
Date: June 24, 2026

In this lively roundtable episode, The Bert Show cast—Bert, Jen, Wendy, Jeff, and friends—swap stories about their recent Valentine's Day celebrations. From romantic dinners and family gatherings to the ultimate adrenaline rush of skydiving, the group blends humor and warmth as they reflect on love, relationships, and weather-induced citywide panic. The highlight: Wendy's bold first date on Valentine’s Day, making for a memorable and relatable conversation about taking chances and savoring unexpected moments.

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Key Discussion Points & Insights

1. The Panel's Valentine's Day Recaps

• Bert’s Weekend with Stacy
  • (01:02–01:41) Bert details a sequence of small, continual celebrations with his partner, Stacy, including a romantic night at the W downtown, flowers from both him and the kids, and the exchange of gifts over the weekend. The variety led to “little things all weekend long, which was really kind of cool.”

2. Wendy’s First Date—On Valentine's Day

• Wendy’s Spontaneous Adventure
  • (01:41–02:07) Wendy recounts her surprising experience:
    • Met a new-to-town guy on Friday night; both open to a date, but she’d be leaving soon.
    • He suggested a dinner date for Valentine's, emphasizing “as long as we’re not ‘Valentine’s,’ let’s do it on Valentine’s Day.”
    • Evening included a nice dinner, movie (“Valentine’s Day”), and “a good time.”
  • Quote:

    “As long as we’re not Valentine’s, let’s do it on Valentine’s Day.”
    — Wendy (01:45)

  • The group reacts warmly; a relatable, lighthearted take on modern dating.

3. Jeff’s Family-Focused Valentine’s & Observing Snow Panic

• Jeff in Syracuse: Contrasting City Mindsets
  • (02:11–03:40) Jeff spends the weekend in snowy Syracuse with his parents and Jessica, highlights “feeding the ducks” as a peaceful highlight.
  • Detailed commentary on how residents in Atlanta panic over an inch of snow, compared to New York’s adaptation.
  • Memorable moment discussing his dad’s perspective:

    “Do you really live in a city where people are that freaked out about being inside with their families for 24 hours?”
    — Jeff’s Dad, via Jeff (02:54)

  • Jeff’s response underscores local culture:

    “People don’t like that thought at all. People really freak out at that.”
    — Jeff (03:31)

  • The cast laughs about traffic jams and people driving “with their hazards on” despite minimal snow.

    “It wasn't even sticking to the ground… people were freaked!”
    — Roundtable Host (03:40)

4. Jen’s Skydiving Date—Taking Love to New Heights

• Jen’s Weekend & Relationship Milestone
  • (03:54–06:47) Jen stays snowed in, enjoys the Olympics, has a lovely dinner—but the big event is her new relationship’s Valentine’s adventure: tandem skydiving.
  • Explains nerves from her first jump (broadcast live on the show), and how this second jump was pure fun, with both she and her partner relaxed and excited.

    “We were just, like, suited up… this was his second jump and my second jump, and so we were just both, like, way more relaxed about it, and it was so much fun.” — Jen (04:54)

  • Describes exhilarating details:
    • Skydiving at The Farm, instructor “Big Steve,” backflips exiting the plane, racing adrenaline, and sub-freezing temperatures at altitude.

      “I totally did that. So I was looking up, eyes open, and we do, like, two flips coming out the back. And I saw the bottom of the airplane. When else in your whole life do you ever see the bottom of an airplane in the air?”
      — Jen (06:07)

  • Promises to upload the video for sharing (“Let’s get it up on the website tomorrow”—06:39).
  • Ends humorously, with Jen’s recurring excitement:

    “All day in the afternoon I was like, hey, guess what? He’s like, what? I’m like, we jumped out of a plane today.”
    — Jen (06:47)

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Notable Quotes and Moments

• Wendy, on her Valentine’s first date:

  “He’s new to town, only been here for about two weeks and wanted to do a date…as long as we’re not ‘Valentine’s,’ let’s do it on Valentine’s Day.” (01:41–01:45)

• Jeff’s observational humor on Atlanta snow panic:

  “The whole city’s got two snowplows and one guy who knows how to drive them.” (03:17)

• Jen’s thrill during skydiving:

  “He was like, make sure you keep your eyes open. You’ll see the bottom of the plane. And that’s a cool feeling.” (05:58)
  “We do, like, two flips coming out the back. And I saw the bottom of the airplane. When else…do you ever see the bottom of an airplane in the air?” (06:07)

• Group laughter about typical Georgia snow reactions:
  “People were driving with their hazards on. I’m like, it’s not even sticking. There’s no ice. There’s nothing.”
  — Roundtable Host (03:40)

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Timestamps for Key Segments

• 01:02–01:41 — Bert recounts his low-key, multi-day Valentine’s celebration with Stacy
• 01:41–02:07 — Wendy describes going on a first date on Valentine’s Day
• 02:11–03:40 — Jeff’s family time, feeding ducks, and Atlanta vs. Syracuse weather story
• 03:54–06:47 — Jen shares her epic Valentine’s skydiving date, including technical and emotional details

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Tone & Takeaways

This episode is classic Bert Show: warm, funny, high-energy, and full of authentic voices. Each cast member’s story brings out a different angle on Valentine’s Day—from romantic partnership to new love, family bonds, and bold adventures. Listeners get both relatability and inspiration: whether you spent Valentine’s Day indoors, out on a date, or jumping out of a plane, the episode celebrates the diversity and fun in how we connect.

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Transcript

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[Roundtable Host]

Okay, our Valentine's Day roundtable here. What everybody do on Valentine's Day on for my weekend, it was kind of a. We did a little of everything this weekend. Friday night was really mine and Stacy's Valentine's night. So we went to the W downtown.

[Jen]

Nice.

[Roundtable Host]

And we ended up in this really cool room that overlooked the city, which was awesome because it was snowing.

[Jen]

Beautiful.

[Jeff]

Oh, that's cool.

[Roundtable Host]

So, yeah, it worked out awesome. And then flowers came on Saturday from me and then the kids sent her flowers also. And then yesterday we opened up our Valentine's Day present. So it was sort of like little things all weekend long, which was really kind of cool. Wendy had a first date.

[Wendy]

I know. First date on Valentine's Day with a guy I met out on Friday night. Wasn't gonna go out, but just met him. He's new to town, only been here for about two weeks and wanted to do a date. And I was like, I'm leaving next week. He was like, let's do it on Valentine's Day. As long as we're not Valentine's. Let's do it on Valentine's Day. And it was a first date. So we went to a really nice dinner, made reservations and then went and saw Valentine's Day, the movie after that, which was really sweet. So had a good time.

[Jen]

Cute.

[Wendy]

Yeah, it was very fun.

[Roundtable Host]

Cool. And Jeff was the lucky of all of us.

[Jeff]

You know what? I actually was in Syracuse for the. For the weekend. We where it snows like, everybody's talking about the snow and everything. And had a great time with just my parents and Jessica and didn't do anything. Hung out, fed the ducks. Fed the ducks. And that was the highlight of the weekend. But had more of an acute awareness of how ridiculous the panic this city feels when there's some snow. Based on one sentence that my dad said when we were at dinner. He says, so everybody's freaking out about the snow. What's gonna happen? I'm like, well, they're just panicked, you know, they gotta get home, they gotta do this. He's like, right, but it's gonna be 50 tomorrow, so the snow will be gone. I said, yes. And he said, do you really live in a city where people are that freaked out about being inside with their families for 24 hours?

[Roundtable Host]

The answer is.

[Jeff]

I was like, yep. Cause that's what people are panicked about when you think about it. Cause, you know, in New York, they're betterly better equipped, the snowplows and salt and all that. So life goes on. So I was trying to explain to him, I said, in Atlanta, people panic because the whole city's got two snowplows and one guy who knows how to drive them. You know what I mean? They're not prepared for that. And he goes, but the snow doesn't stay.

[Jen]

So you just stay inside.

[Jeff]

So you gotta just stay inside with your family for a day. And I'm like, yeah, people don't like that thought at all. People really freak out at that.

[Roundtable Host]

Friday night, the traffic was so bad. People were freaking so bad. And it wasn't even sticking to the ground. And people were freaked. I was driving downtown and, like, people were driving with their hazards on. I'm like, it's not even sticking. There's no ice. There's nothing.

[Spin Quest Player]

People chill.

[Roundtable Host]

But Jen's Valentine's Day, this was pretty cool yesterday.

[Wendy]

So excited to get it.

[Jen]

It was definitely a cool weekend. I did use the excuse Friday night to sort of stay snowed in, which was really nice, and watched the Olympics. And then Saturday was sort of going out to a nice dinner. We went to one midtown Kitchen, which was great. And then to Bitterball. And then yesterday, we celebrated Valentine's Day, and this is the new relationship by jumping out of an airplane. So we went skydiving yesterday, which was incredible. It was my second time going. You guys know, I jumped on the air the very first time, and I had so much anxiety and nerves in the airplane going up. But I think it was because of the broadcast. You know, I was Just so concerned about it, you know, airing live on the bird show. And could you guys hear me? Because that airplane, you know, they're tiny little, you know, tiny little planes. And so it's so loud up there, you can't really hear anything. I was, like, so stressed the first time about making sure you guys heard me. And it was, you know, with two of my girlfriends and this, like, totally, like, emotional time in my life and this, like, you know, big, like, sort of emotional outpouring experience that came along with it that first time. Well, this time was completely different. Just fun. Like, no radio work to worry about or whatever. We were just, like, suited up, and of course, we both jumped tandem, but this was his second jump and my second jump, and so we were just both, like, way more relaxed about it, and it was so much fun. It was awesome. It was freezing yesterday.

[Roundtable Host]

Yeah, I was talking to them Saturday

[Jen]

night about this 14,000ft.

[Roundtable Host]

Was it, like, how cold was it?

[Jen]

They say it was 30 degrees colder up there than it is here. So it's probably what, like, 10 degrees maybe?

[Wendy]

Oh, wow.

[Jen]

Yeah, it's probably 10 degrees. Maybe 15 or 20 up there. I don't know. But you're just, like, so intensely with adrenaline, you kind of, like, forget about temperature or any of that stuff. But it was awesome. He made all of the plans. And so we jumped at a different place that I had been before. We went to the farm, and I jumped with a guy named Big Steve.

[Spin Quest Player]

Big Steve.

[Jen]

Big Steve was awesome. And so he knew that it had been my second jump. So he was like, do you want to do some cool stuff? And we get out of the plane. I was like, yeah. And he's like, let's do some backflips.

[Jeff]

I'll show you how big I can get.

[Jen]

And so we. So we sort of, like, jumped and turned and did two back flips coming out of the airplane. And he was like, make sure you keep your eyes open. You'll see the bottom of the plane. And that's a cool feeling. So I totally did that. So I was looking up, eyes open, and we do, like, two flips coming out the back. And I saw the bottom of the airplane. When else in your whole life do you ever see the bottom of an airplane in the air?

[Roundtable Host]

Only if I'm laying on my back and I'm on a Runway.

[Jeff]

Guess what? Everybody on Lost has seen that. Big deal.

[Roundtable Host]

So now you've got a video again of it, right?

[Jen]

Yeah, I do. I do. I have a video from the place. So maybe I'll try to get that up on YouTube. I don't really know how to do all this stuff.

[Roundtable Host]

Let's get it up tomorrow. If it's 24 hours, we'll put it

[Jen]

up on the website tomorrow. Okay. Yeah, that'd be awesome.

[Roundtable Host]

Okay, cool. So you can see Jen jump out of the plane tomorrow. Well, congratulations. Awesome.

[Jen]

It was a blast. It was so much fun. And then like all day in the afternoon I was like, hey, guess what? He's like, what? I'm like, we jumped out of a plane today.

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