Vault: She Wants To Date Someone Who Has Been Married Before

Summary

The Bert Show – Vault: She Wants To Date Someone Who Has Been Married Before

Episode Date: May 22, 2026

Episode Overview

This episode dives into Jen’s unique dating “filter”: her preference to date men who have previously been married. The Bert Show cast—primarily Jen, Melissa, Wendy, and Jeff—unpack the reasoning, stigma, and cultural shifts behind viewing prior marriage or divorce as a potential asset rather than a drawback. There’s genuine, relatable discussion about dating in your 30s and 40s, including personal insecurities, generational differences, and the oddly tricky world of dating as a local personality. Listeners also contribute personal experiences and challenge or validate the cast’s points along the way, keeping the tone open, real, and funny.

---

Key Discussion Points & Insights

Jen’s “Been Married” Dating Filter

• Jen opens up about a great recent first date but keeps details vague (01:43).
• The episode pivots to her desire to date someone who has been married before.
  • Jen: “I would like to meet somebody who had been married before. I’ve been married before. So right off the outset, there’s a judgment feeling about that... you just feel like you got a big stamp on your forehead” (02:38).
  • She feels a pre-existing relatability and less judgment when both parties are divorced (03:00).
  • There’s comfort in knowing the other person has navigated commitment and might be more open to it—or at least understands its weight.

Perceptions and Stigmas of Being (or Not Being) Married

• Jen theorizes: if someone is “smart, good looking, successful... but not married before” in their mid-30s or beyond, it might signal commitment issues (03:44).
• Melissa: “If you’re really that great, why hasn’t someone snagged you up to this point?” (03:51).
• Jen, clarifying: it’s less about ‘snagging’ and more about the willingness/ability to commit (04:00).

The “DINK” Discussion

• The crew jokes about acronyms, initially misusing “DINK” as “Divorced, No Kids.”
  • Melissa: “Divorced people with no kids are called DINKS” (05:17).
• A listener corrects them: DINK actually stands for “Dual Income, No Kids” (07:30; 07:35).

Shifting Social Norms for Divorcees

• Wendy finds it “fascinating” that, culturally, having been divorced is now sometimes seen as a plus.
  • Wendy: “...now that is something that's positive... where... especially on women, if you’ve been divorced before… now it’s an asset to have been married rather than not” (04:17).
• Jen and the other women discuss how dating life is different in the modern era versus two decades ago—when Jen and Wendy both recall real stigma.

Dating as Radio Personalities

• The cast commiserates about unique struggles: dating while being public figures means their lives, schedules, and even dates are on-air fodder.
  • Jeff: “You can’t go on a regular date. And I will say... one of the things that made me get to a second date with Katie... is the fact that Katie... didn’t act like she listened to the show... that was so refreshing” (05:55–06:27).
  • Wendy: “If you’re going to get in a relationship... this show is not going to be the most important thing in that relationship” (06:33).

Listener Perspectives

• Julie (Caller): Shares she didn’t marry until 37 and felt judged; she wanted to “do it right,” despite pressure. Message: “wait until you’re ready” is smart, but every story is different (07:51–08:29).
• Jen gently pushes back, noting every individual’s path is valid and not to assume “waiting” is inherently superior (08:29).

Approaching the Hosts – Lighthearted Moments

• A humorous exchange unfolds:
  • Melissa (joking): “Both Wendy and Jen just appreciate a good junk press. So what you try to do is just get physically close... and push your pelvis into—” (09:40).
  • Jen (deadpan): “Please don’t do that” (09:54).
• The group agrees a normal “hi” is best, and Melissa shares the best opener is an invite to a fun event, like “Want to go to the SEC championship?” (10:08–10:16).

---

Notable Quotes & Memorable Moments

• Jen (on shared marital status): “You can’t understand it until you’ve gone through it and been there.”
  • [02:38]
• Wendy (on divorce as an asset): “Now it is something that’s positive... now it’s an asset to have been married rather than not.”
  • [04:17]
• Melissa (misdefining DINK): “Divorced people with no kids are called DINKS.”
  • [05:17]
• Listener correction: “DINK stands for Dual Income, No Kids.”
  • [07:35]
• Jeff (on refreshing dates): “If you can go an entire conversation without mentioning [the show], points, because you want to make sure that the person’s there [for you].”
  • [06:27]
• Jen (on approach lines): “Just hi, come up and have a normal conversation.”
  • [10:08]
• Melissa (humor): “Both Wendy and Jen just appreciate a good junk press...”
  • [09:40]
• Jen (deadpan): “Please don’t do that.”
  • [09:54]

---

Timestamps for Important Segments

• 01:43 – Jen reveals she had a great first date
• 02:38 – Jen discusses her comfort in dating someone previously married
• 03:44 – The group debates what it means if someone hasn’t married by their late 30s/40s
• 05:17 – Misunderstanding and correction about “DINKS”
• 06:27 – Jeff and Wendy on the challenge of dating as local celebrities
• 07:51 – Listener shares personal experience marrying later in life
• 09:40 – Lighthearted advice about how to approach the show hosts
• 10:08 – Hosts agree, “just say hi” as a best opening line

---

Tone and Style

The episode is candid but light-hearted, full of playful ribbing, supportive women’s talk, and self-aware humor. While delving into the emotional complexities of dating after divorce, the style remains conversational, inclusive, and often funny.

---

Summary Takeaway

This Bert Show episode insightfully explores the emotional, practical, and even cultural logic behind seeking partners with similar marital histories—especially after divorce. With frankness and wit, Jen and her peers demystify the stigma around divorce, ultimately encouraging listeners to consider that everyone’s relationship path is valid, and relatability and timing may be more important than fitting traditional expectations.

The cast’s signature blend of humor, realness, and relatability ensures the topic is approachable, relevant, and surprisingly affirming—whether you’re single, married, or divorced.

Transcript

[Lowe's Announcer]

During Memorial Day at Lowe's. Shop household must haves for less. Save $80 on the Char Broil Performance Series 4 Burner Grill to chef up something special, plus get up to 45% off. Select major appliances to keep things fresh. Our best lineup is here at Lowe's Lowe's. We help you save valid through 527 while supplies last selection varies by location. See Lowes.com for details.

[Jen]

Visit your nearby Lowes.

[IQ Bar Announcer]

This podcast is sponsored by IQ Bar.

[Will (IQ Bar Creator)]

I've got good news and bad news. Here's the bad news. Most protein bars are packed with sugar and unpronounceable ingredients. The good news? There's a better option. I'm Will and I created IQ Bar plant protein bars to empower doers like you with clean, delicious, low sugar, brain and body fuel. IQ bars are packed with 12 grams of protein, brain nutrients like magnesium and Lion's Mane, and Zero Weird Stuff. And right now, you can get 20% off all IQ Bar products, plus free shipping, clean ingredients, amazing taste, and you'll love how you feel. Refuel smarter, hydrate harder, caffeinate larger with IQ Bar.

[IQ Bar Announcer]

Try our delicious IQ Bar Sampler Pack with nine plant protein bars, eight hydration mixes, and four mushroom coffee sticks. And now you can get 20% off all IQ Bar products, plus free shipping. When you go to iqbar.com today and enter promo code BAR20 to get this exclusive offer for our listeners. That's iqbar.com promo code BAR20 to get 20% off plus free shipping. Iqbar.com, code BAR20.

[Lowe's Announcer]

You're on the vert show.

[Melissa]

I don't think Melissa or Wendy or I or any of our interns or anyone who's been around you physically today can avoid the fact that you have been giddy.

[Jen]

Yeah, kind of. Yeah.

[Melissa]

So tell us about Saturday.

[Jen]

Well, I don't know how much I can tell you about it, except that I had a first date Saturday that was great. Okay, really great. But, like, if you say too much, I don't know, you can't say too much.

[Wendy]

Well, here's something that keeps it generic. If we don't say. If we don't say anything else, let's not say anything else. Except I think, Jeff, correct me if I'm wrong, that the interesting part of the conversation, I think that listeners can be peeked into is the marital status, like, of past marital status of him. Can we talk about that or.

[Jen]

No, I can just. I'll talk about my feelings on that in generic.

[Wendy]

Yes, let's go with that. Let's do that. We won't talk about him. But I thought the concept of this being kind of a filter in your mind was interesting.

[Jen]

Right. So the filter is. And I've been talking to my friends about this, and I'm really like, I've been in a space where I'm open to dating as a verb.

[Caller/Listener]

Right.

[Jen]

We've talked about that. So that's anybody, everybody or whatever. But I was talking to some friends of mine and I was saying, I would like to meet somebody who had been married before. I've been married before. So right off the outset, there's a judgment feeling about that. And you can't understand it until you've gone through it and been there. But you just feel like you got a big stamp on your forehead or whatever.

[Melissa]

Big D, the Scarlet letter type thing.

[Jen]

Exactly. And so for me, that would be a comfortable situation, not saying that another situation might not work out great or

[Wendy]

whatever, unless there's a relatability there.

[Jen]

Right. It would be a relatable thing. And right off the bat there wouldn't be any judgment. And then I also was saying. Saying that I felt like if I found somebody that was my age or older and married before, that that would be a good thing because. And this is gonna sound really bad about if anybody hasn't been married before, but my theory was that maybe there was something wrong or there was commitment issues. If somebody had been smart, good looking, successful, and all these other things, but

[Wendy]

not married before, in their mid-30s and up, if they have never been married.

[Jen]

Yeah, like late 30s, late 30s.

[Melissa]

Like, if you're. If you're really that great, why hasn't someone snagged you up to this point?

[Jen]

No, not necessarily that. It's more like.

[Melissa]

I didn't think so.

[Jen]

It's more like commitment issues.

[Melissa]

Right.

[Jen]

If you haven't tried it by 40, why not? And would you ever be somebody that would be open to commitment? So that's what I was saying to my friends. I said, I want to meet a nice boy who's been married before, which

[Wendy]

I think is funny.

[Jen]

And I've been saying that for about

[Wendy]

the last month because I don't think that it's. I don't think it's unique that Jen feels that way, that I think a lot of women probably feel that way about guys. Like, if you haven't been married by 40, and like you said, you have all these attributes, then what's going on? And I just found it fascinating that now that is something that's positive. If you've been Divorced where? I mean, even though I'm surprised, for me, I'm surprised that Jen still feels a sense of judgment because my sister was divorced long time ago and she definitely felt it back when she got divorced some 20 years ago when there was definitely judgment on. Placed especially on women, if you've been divorced before. So I just find it fascinating that it's now an asset to have been married rather than not. You know what I'm saying?

[Jen]

Yeah, it's not. Yeah, it's. It would definitely be an asset to me.

[Caller/Listener]

Right.

[Jen]

I'm sure to other women it wouldn't be. But what do we call it? I wanted. Oh my friends and I said that we wanted somebody that was dying and k. Divorced, no kids.

[Wendy]

Dinks.

[Melissa]

That's Dinks. That's a real category.

[Jen]

Really?

[Melissa]

Uh huh. Divorced people with no kids are called Dinks.

[Jen]

Really?

[Melissa]

Huh. You thought you were all creative and whatnot.

[Wendy]

I mean, no, it was yours. It was all yours.

[Jen]

No. Yeah, I didn't come up with the actual name for it, but yeah.

[Melissa]

So that's a good. There's a promotion idea right there. A Dinks party. There you go. Hosted by Jen.

[Jen]

That's right.

[Melissa]

So yeah, we've learned. And by we, I'm only referring to Wendy and Jen and well, Melissa to some extent anybody who spent any time single on this show. Oh my God, that is certainly exploited.

[Wendy]

Totally did. Yes. It sucked because it, because it's.

[Jeff]

Because the guys listen, it's just, I

[Wendy]

mean it seems like, oh my God, you know, you're on the air and you could, you know, exposing yourself and you could have anybody in the city, you know, but it's like you can't go on a regular date. You can't go on a regular date. And I will say that one of the things that made me get to a second date with Katie that we've talked about since then is the fact that Katie at the time didn't act like she listened to the show. She didn't ask me a thing about me or a thing about the show. And that was so refreshing that she got a second date on that.

[Jeff]

I'll agree with that one. If you can go an entire conversation without mentioning it points because you want

[Wendy]

to make sure that the person's there. Because if you're going to get in a relationship with somebody, this show is not going to be the most important thing in that relationship. So you don't want somebody that's sitting there across from you just like, oh my God, I'm such a Burt show fan. And I just listened to Burt show. It's like, God, I can't do it.

[Melissa]

Just for the record, if you're trying to wow me, talk really a lot about me. Talk about how you listen to me on the show.

[Wendy]

Hey, Jeff.

[Jen]

How I say you're married? Honey, I'm just saying, Wendy, you can understand this too. It's also difficult because if you have, say there's different dates that are set up. Like you can't.

[Wendy]

Yes.

[Jeff]

Cause they're gonna know about them.

[Jen]

Right.

[Jeff]

And you're not leaving anything to their imagination. You know how we're supposed to play the game and we're supposed to be unavailable? Well, they can tell when you're available and not available because you're talking about

[Jen]

it all the time.

[Wendy]

Your life on the air.

[Jen]

Right.

[Melissa]

I was wrong by that Dink thing. I was wrong.

[Jen]

What does that mean, Melissa?

[Melissa]

You were wrong with me. So I'm not alone.

[Wendy]

No, I wasn't. Hey, Kelly, I didn't take you.

[Melissa]

Hey, what's up?

[Caller/Listener]

Love this show. Thanks a lot. Dual income, no kids is what Dinks stands for.

[Jen]

Dual Inc. So you and Jessica are Dinks?

[Melissa]

Yes, F you start calling names.

[Wendy]

Thank you.

[Caller/Listener]

Have a great day.

[Wendy]

Thank you.

[Jeff]

Dink.

[Melissa]

Hey, Julie. Welcome to the bird show.

[Caller/Listener]

Oh, thank you.

[Wendy]

Hi.

[Caller/Listener]

Hi. I just wanted to make a comment that I didn't get married until I was 37. And I had people looking down on me, asking me if I didn't like the institution of marriage, what was my problem? And there wasn't a problem. I love the institution of marriage, but I only wanted to do it once. I wanted to wait until I did it right now. I had been engaged twice before. Everybody else was getting married when I broke up my engagements. And the only smart thing my sister in law ever said to me is, wait until you're ready. Your friends will be divorced two and three times. When you finally find somebody, it'll be a while, but you'll do it. For I'd never get married after a while. For I'd never have kids. I've been married eight years with two kids.

[Jen]

Yeah, I mean, I think that's good for you, that that's your story. But I also think that that was kind of judgmental to be like. And her path was better. Right. Like, well, I waited, so my decision was better. I don't think that's necessarily the right thing.

[Melissa]

It's not a statement. Keep in mind, a lot of times we say stuff on the show, we stay like they are. Our personal opinions, like, you don't like we're not standing on the mountain and dispelling what we think is the gospel to the masses.

[Wendy]

Well, she was sending. But I. Yeah, I agree that. I think that you end up. You want to be. You want to relate to who you're with. And for some people, you know, waiting. Like, for instance, myself waiting to have children until I'm probably gonna be in my 40s. Being the older mother is what's right for me. But I totally can see the benefit of having had kids in your 20s. You know what I mean? But. So one decision is not better than the other.

[Melissa]

Hey, Paul. What's going on?

[Caller/Listener]

Hey. I was just wanting to comment on Jen. Hobbies. Dating with guys. Or maybe even Wendy with guys. Maybe people don't know or guys don't know how to approach them because they are so popular.

[Melissa]

Well, we've talked about this on the show before in Both Wendy and Jen just appreciate a good junk press. So what you try to do is just get physically close to them and push your pelvis into.

[Jen]

Please don't do that.

[Melissa]

No, it's not right.

[Jen]

Hi. Works only just because that's what you do. Doesn't work for everyone.

[Melissa]

I thought you guys were into that. Mistaken. What would be the best opening line for a guy to use on either one of you?

[Jeff]

Just hi, Come up and have a normal conversation.

[Melissa]

Give me a drink. Wendy had one this weekend. You want to go to the SEC championship?

[Jen]

That was it.

[Melissa]

Listen, it's the vert show

[Lowe's Announcer]

during Memorial Day at Lowe's Shop household must haves for less. Save $80 on a Char Broil Series 4 burner grill to chef up something special. Plus get up to 45% off select major appliances to keep things fresh. Our best lineup is here at Lowe's. Lowe's. We help you save valid through 527 while supplies last selection varies by location. See lowe's.com for details.

[Jen]

Visit your nearby Lowe's.