Vault: The Holidays Hit Different When You're Alone

Summary

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The Bert Show: "Vault: The Holidays Hit Different When You're Alone"

Date: May 6, 2026

Episode Overview

This episode of The Bert Show delves into how the holiday season can feel uniquely challenging for those who are newly single. With a conversational and authentic tone, cast members share personal experiences, discuss the pressures single people face during family gatherings, and swap ideas on how to beat the “holiday blues.” The episode features anecdotes, honest vulnerability, and practical suggestions for making solo holidays more enjoyable.

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Key Discussion Points & Insights

The Unique Stress of a Single Holiday Season

• Opening Reflection:
  At [01:54], the conversation begins as one of the hosts, Jen (speaker C), describes discussing plans for Thanksgiving and Christmas with a newly single friend.

  • Quote:
    “It's a tough time of year, I think, to be single.”
    — Jen, [01:59]

• Family Dynamics and Societal Expectations:
  Dealing with family get-togethers tends to bring out uncomfortable questions and implied pity about single status.

  • Quote:
    “There's some sort of, like, implied, like, pity or something on single people… It's almost like annoying and frustrating.”
    — Jen, [02:27]

Coping Strategies for Beating the “Holiday Blues”

• Shortening Family Visits:
  Jen and her friend consider spending less time with family to avoid prolonged discomfort.

  • Quote:
    “Extended period of time at home... just gets depressing, I think...”
    — Jen, [02:54]

• Planning a Getaway:
  Instead of enduring the holiday lull between Christmas and New Year’s, Jen and her friend contemplate a trip together immediately after festivities wrap up.

  • Quote:
    “We're going to plan it where we're leaving Christmas night. Like, festivities are over. Okay.”
    — Jen, [05:04]

First Time Navigating Holidays as a Single Adult

• Personal Milestone:
  This will be Jen’s first winter holiday season single since age 19 ([04:28]).
  • Quote:
    “So the first time since you were 19 that you're single, single.”
    — Co-host, [04:35]

Friendships, Travel, and Changing Plans

• Potential Trip Complications:
  The group jokes about what happens if one friend finds a new relationship before the trip, leaving the other to travel solo.

  • Quote:
    "Oh, that would suck. If you and your single friend planned a trip and then one of y'all start dating somebody..."
    — Jen, [04:41]

• Excitement of Exploring Together:
  The idea is to make the post-holiday period something to look forward to, potentially traveling abroad (Europe is mentioned).

  • Quote:
    "Having something like that is gonna make getting through that sort of holiday bluesy feeling... it's a great idea."
    — Jen, [06:29]

Caller Stories: Single Holidays and Unexpected Romance

• Wendy’s Story:
  At [07:47], a listener named Wendy calls in to share how her single Thanksgiving unexpectedly led to reconnecting with her fourth grade boyfriend—and eventually becoming engaged.

  • Quote:
    “We were drinking wine, ended up on Facebook, ended up reconnecting with my fourth grade boyfriend, and now we're engaged.”
    — Wendy, [08:06]

• Hosts' Perspective on Destiny:
  The hosts frame Wendy’s story as an example of fate stepping in when holiday plans change ([08:19]–[09:04]).

Humor and Real Talk

• The “Single Bluesy” Ritual:
  The group recognizes the sometimes-pathetic rituals of single people during the holidays—wine, social media, and aimless planning—but with humor and camaraderie.

  • Quote:
    “That is such a single bluesy thing to do though. Refuse to hang out with family, with your girlfriend, drinking wine, on Facebook.”
    — Jen, [09:04]
  • Quote:
    “So pathetic.”
    — Co-host, [09:14]

• Anticipation and Motivation:
  The cast encourages Jen and her friend to go for their trip, acknowledging that the holidays book up fast and committing to plans takes a real act of will.

  • Quote:
    “If you're going to do it, you got to pull the trigger on it now.”
    — Co-host, [09:50]

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Notable Quotes & Memorable Moments

• On Leaving Quickly After Christmas:
  "We're going to plan it, like, where we're leaving Christmas night. Like, festivities are over."
  — Jen, [05:04]

• On Facing a New Kind of Holiday:
  "This is going to be your very first holidays. Single."
  — Co-host, [07:24]

• On Making the Best of It:
  "This one sounds like a great one… I think it'll be this sort of like beacon of something like super exciting to look forward to."
  — Jen, [09:36]

• On Unexpected Love:
  "Ended up reconnecting with my fourth grade boyfriend, and now we're engaged."
  — Wendy, [08:09]

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Timestamps for Important Segments

| Timestamp | Segment Description | |------------|------------------------------------------------------| | 01:54 | Episode content starts; discussing singlehood & holidays | | 02:35 | Family reactions and frustrations as a single person | | 03:24 | Importance of holiday traditions and the post-Christmas lull | | 04:28 | Jen’s first single holiday since adulthood | | 05:18 | Planning post-Christmas travel as a coping strategy | | 06:29 | Considering an overseas trip—turning holidays into adventure | | 07:47 | Wendy calls in with a story of singlehood and unexpected romance | | 09:04 | Humor around “single blues” rituals | | 09:50 | Urgency to book travel—final encouragement |

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Final Thoughts

The episode captures the bittersweet, sometimes comical reality of the holidays for those who find themselves single, especially after years of celebrating as part of a couple. The hosts and callers normalize the experience, offer practical advice, and encourage listeners to embrace new adventures, whether that means booking a spontaneous trip or simply allowing fate to take its course.

Tone: Relatable, humorous, empathetic, and conversational—making the subject accessible and less daunting for anyone feeling anxious about the solo holiday season.

Transcript

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[C]

The bird show was talking to one of my girlfriends last week and she and I are both single now, newly single and you know, kind of having a hard time with it. And we were just talking about the holidays coming up and what everybody's plans are gonna be for Thanksgiving and for Christmas and all that kind of stuff. And you know, she's just realizing that it's, it's a, it's a tough Time of year, I think, to be single. Mm, absolutely. You know, because it's like you're going back to, like, family and everybody wants to know what's going on with you or whatever. And there's some sort of, like, implied, like, pity or something on single people, you know, and it's like almost. It's almost like, annoying and frustrating, and

[D]

people are like, you're single.

[C]

Oh.

[D]

And it's the holiday towards the house.

[C]

Oh, yeah. It's like this sort of, like, pity party thing or whatever. And it's like, no, really, it's gonna be okay. So I don't know. We were just trying to figure out, like, ways, like, the best ways to sort of, like, beat the holiday blues. And I think we're both shortening our trips home to see our families.

[E]

You're shortening?

[C]

I think so, because, like, extended period of time, like, at home. I don't know, it just gets depressing, I think, like, wow, I'm totally.

[D]

Did you see your mom?

[E]

I'm looking at you totally. Like, I can't understand where you're coming from, because I would assume, especially with a family as tight as yours.

[C]

Oh, my God, my family's amazing, right?

[E]

You want to spend more time with them around that time.

[C]

Well, and specifically, we're talking about that week between Christmas and New Year's. You know what I mean? Because, like, going home for Thanksgiving is kind of like a quick, short trip anyway.

[E]

Right.

[C]

And then going, like, before Christmas, you're still excited and you're doing all those kind of like, fun, traditional things. You're cooking food and you're going shopping and you're wrapping gifts and, you know, all the excitement and all that stuff, like, leading up to Christmas. But it's the day after Christmas and that time to New Year's Eve. Like, if I sat home with my folks for that week, I would probably want to shoot myself. I think I really would not because I don't love my family, but just because. Whatever. So we've decided to sort of, like, battle the. The potential single person blues. Like, during that time, we're going to just try to take a fantastic trip together.

[E]

I'm trying to get the timing down, right, of this whole thing. Were you single last year? Around the holidays?

[C]

Dating.

[E]

Dating. So you did have. I mean, you were dating somebody, but

[C]

it was still a little depressing. I mean, it's just. It's just a weird thing to be, like, home with your family and I

[E]

don't know, because, I mean, because this is going to be unusual for You. Because you and Ryan were with each other since you were 19, right?

[C]

Right.

[E]

So you've always had somebody in your life around the holidays.

[C]

Definitely.

[E]

So this is. And this year, you are single. Single, single, single, single. So the first time since you were 19 that you're single, single.

[D]

Well, there's plenty of time between now and Christmas. She could be engaged.

[C]

That's true. I'll just do that to avoid the holiday blues, right? Oh, that would suck. If you and your single friend planned a trip and then one of y' all start dating, somebody says, you know what? I'm going to back out of the trip. And the other one's like, okay, I'll take a trip by myself.

[E]

Hey, Jen, I found somebody. I can't go on our singles trip.

[D]

When did you go to the resort? Hacienda de la Fernando?

[C]

Oh, that was last September.

[D]

Oh, I thought those holidays.

[E]

Yeah.

[C]

No, you mean when I went to Mexico. Yeah, it's funny the way he phrased that. But anyway, we're just going to try to plan a trip, and it's been like, we're going to plan it, like, where we're leaving Christmas night. Like, festivities are over. Okay.

[E]

You're not wasting any time gone.

[C]

Like, we are both, like, not going to have that happen. Uh, forget it. So, yeah, so that's kind of the plan. Right now. We're trying to figure out exactly where

[D]

to go in the same city in Florida. Will you be able to leave?

[C]

No, we might leave from different cities or come back to Atlanta and connect and do a red eye that night.

[D]

Cause what if you got to the other city and your friend just didn't show up? And then you check your phone and there's a text message, I'm sorry, I just can't do it. Having too much fun with my family. Like, you're, like, in the Buenos Aires airport going, fernando,

[C]

This is so inside. Don't even watch your time.

[E]

Well, it won't be when we explain that when Jen went to Mexico, she met a very interesting yoga instructor named Fernando.

[C]

Fernando.

[E]

So the what I my thinking on the whole deal is, if you do take off Christmas night and you guys end up on a destination with each other, you know, together, but separate. That when you get to where you're going, you're gonna be around people just like you, which will be awesome.

[C]

Yeah.

[E]

Cause they're all in the same place. I just had to get away from my folks.

[C]

Exactly. Yeah. And we're even talking about potentially going to Europe. So that's like. I think that, like, Having something like that is gonna make getting through that sort of holiday bluesy feeling. It's a great idea, like, you know. Cause it's like something to look forward to. And we're gonna be about like, you know, trying a new place together, exploring somewhere new. We're just trying to figure out if we can figure afford the flights and afford that kind of a trip. Like, you know, that's kind of a quick turnaround to go somewhere that far. But we're like, you know what, let's just do it. Like that'll be our Christmas present to ourselves or whatever. Like just to. Just to have that to look forward to, you know. Cause it's awesome to spend time with family. And I have an amazing family in Florida. Like my aunts and uncle and my cousin and her kids. And like, it's just this like whole big crazy family, which is awesome. But I think like that lull afterwards could seriously send me to like Lexapro land.

[E]

Especially because it really is the first time you're doing it as an adult. You're how old now?

[C]

32.

[E]

And this is going to be your very first holidays. Single.

[C]

Single, I guess since 19.

[E]

I mean, this is your first one as an adult.

[C]

Yeah.

[E]

That's exciting.

[C]

You just got to. You both have to commit to the trip though. Oh yeah, the trip. Now once we're. Once we can figure out the flights and once it's booked, oh, it's done for sure. Ten months from now, something happens in one of yalls personal lives. You have to dick with the committed.

[E]

Hey, Wendy, Good Morning. You're on Q100.

[F]

Hey. I was just going to tell Jen. Jen. Last Thanksgiving, I was supposed to go to Las Vegas last minute. My mom backed out of daycare for me. I didn't have childcare. So I ditched my family and refused to go to Thanksgiving. I stayed home with my girlfriend. We had this exact same conversation that you had with your girlfriend. We were drinking wine, ended up on Facebook, ended up reconnecting with my fourth grade boyfriend, and now we're engaged.

[E]

Whoa, whoa. That's a roundabout story in a very short amount of time.

[C]

Wait, how did it go down? You went on Facebook and you found him on a wine night, and then did you all ever do a trip? I'm confused.

[F]

Well, we ended up not ever doing our trip. We did it in March for my girlfriend's birthday. But he and I were together then, so I went on a girls thing. Anyway, later. But we were just at home goofing around. My girlfriend looked at old Exes. And she was like, hey, you know he's on here. And I said, oh, I think he's married. She said, no, it says he's single. So I sent him a message. The day after Thanksgiving, we had coffee and that's all she wrote.

[E]

Now let's look at this through the eyes of destiny, okay? Because she wasn't supposed to be there that day. She was supposed to be somewhere else.

[C]

Yep.

[F]

I was supposed to be in Vegas.

[E]

And she points, she gets pointed in the direction of fourth grade dude. And sure enough, connection on that day. That is destiny right there.

[C]

That is such a single bluesy thing to do though. Refuse to hang out with family with your girlfriend drinking wine on Facebook.

[F]

Yeah, sorry.

[C]

So sad about that.

[E]

So pathetic.

[C]

Like, really. And that's what we did last weekend. We were like Saturday night sitting on the couch, having wine and we were on Orbitz. We were not on Facebook. We were like looking on, you know, to look for travel or whatever.

[E]

But sometimes those trips in your mind, they don't seem to make sense unless you're all wind up or whatever. But this one sounds like a great one.

[C]

I think it'll be this sort of like beacon of something like super exciting to look forward to.

[E]

Great idea. Yeah, good for you.

[C]

We'll see. I'll let you know if we actually

[E]

book it at 6:27 right now. You guys are going to have to do something quickly though, because that's the time of year where everything books up fast.

[C]

Yeah, I know.

[E]

So if you're going to do it, you got to pull the trigger on it now.

[C]

Yeah, we're. We're talking about maybe doing it this week.

[D]

Do it.

[C]

Great. Yeah.

[B]

This is the bird show.

[G]

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