Vault: She's Engaged To Multiple Men?!

Summary

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The Bert Show – "Vault: She’s Engaged To Multiple Men?!"

Date: January 26, 2026
Host: The Bert Show Cast
Main Guest: "Angela" (on a voice disguiser)

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Overview

This lively episode of The Bert Show revisits a jaw-dropping listener drama that originally unfolded before the holiday break: a woman named Angela calls in to discuss how she ended up engaged to three men at once, and how her current love life has gotten even more complicated. The cast digs into Angela's wild relationship history, the morality of her choices, and whether she just loves “the celebration of herself.” The hosts provide humor, skepticism, and invite listeners to weigh in, leading to a fast-paced, hilarious, and occasionally head-shaking exploration of modern romance.

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Key Discussion Points & Insights

1. "The Engagement Juggle": Angela's Story Unpacked

• Angela reveals she was engaged to THREE men at the same time:
  • First, a high school sweetheart (engaged, wedding set four years in the future after college).
  • While still engaged, she meets and agrees to marry a college boyfriend (wedding planned for after graduation).
  • Upon getting a job abroad in England, she meets a third man, also gets engaged.
  • She maintains involvement—at times overlapping emotionally and logistically—with all three (00:31–01:35).
  • Quote:

    “It wasn’t two. Sorry. It was three.” – Angela (00:31)

2. Holiday Gift Dilemmas & Relationship Honesty

• Angela admits she sometimes stays in relationships just long enough to get holiday gifts before breaking up.

• The cast debates the morality/hypocrisy of this, sharing laughs and their own tongue-in-cheek "guidelines" for breakups around the holidays.

• Angela receives lavish gifts—a Tiffany diamond tennis bracelet and earrings for her birthday and a Wii for Christmas (03:39–03:43).

  Quote:

  “He gave me a diamond tennis bracelet from Tiffany's... and for Christmas, I got a Wii with all the freaking accessories. It was great.” – Angela (03:39)

3. The Birthday Party Bombshell Proposal

• Angela’s mom throws her a huge 30th birthday party, inviting friends from high school and college—even international pals.

• Her high school sweetheart unexpectedly attends, and by the end of the night, proposes to Angela with a massive ring. She says yes—while still engaged to her current fiancé (04:00–05:03).

  Quote:

  “At the end of the night, he proposes with a freaking huge ring... What do you think I said? This is Angela, the black widow here. I said yes.” – Angela (04:01, 05:01)

4. Who Knows What? Layered Secrets & Double Engagements

• Angela's current fiancé is unaware she’s accepted another proposal; her high school sweetheart does know she’s engaged to someone else.

• She reveals how she juggles the engagement rings: wearing one, hiding it in the car when seeing the other guy (05:36–05:51).

• The hosts express both amazement and disapproval over how lightly she takes these relationships.

  Quote:

  “I wear his—the high school sweetheart ring, because it’s huge, and I just kind of take it off and put it in the ashtray every time I see my first fiancé.” – Angela (05:40)

5. The Psychology: Love, or Just Loving the Attention?

• The cast challenges Angela: Does she love these men? Or love the parties, rings, and celebrations?

• Angela insists she genuinely loves her current fiancé and wants to marry him, but can't ignore longstanding feelings for her high school sweetheart (07:13–07:44).

  Quote:

  “You just like the celebration of you… You like to get presents on Christmas. You like birthdays thrown for you. You like engagement rings… Do you really love this guy?” – Host (07:00)
  “I really love, I guess my current fiancé… but that’s my high school sweetheart. I’ve loved him for so long.” – Angela (07:13)

6. Listener Reactions: Gold Digger Accusations and Tough Love

• Multiple female callers express strong skepticism, calling Angela a gold digger, a narcissistic liar, and “crazy” (08:14–11:29).

• One caller, Sarah, shares she was once engaged six times before marriage—then divorced—and urges Angela to "back away from Mr. High School" for everyone's sake (11:29–12:02).

  Memorable Line:

  “You’re toying them like they’re catnip and you’re a cat.” – Host (09:49)

7. The Moral Debate: Is Angela Doing Anything Wrong?

• Angela claims she has done no intentional wrong, arguing she simply accepted a proposal that “just happened.”

• The hosts and callers push back, saying turning down the proposal, or telling the truthful situation, would have been the right thing.

• Angela says she’ll eventually tell her fiancé, but “couldn’t find the right moment.” (08:21–08:39)

  Quote:

  “I did not do anything wrong because I’m not out there...” – Angela (14:58)
  “You already engaged!” – Host (15:14)

8. The Cliffhanger: What's Next for Angela?

• Angela admits she's never actually been married—she just gets engaged.
• She claims her intention is to marry her current fiancé, but the cast and listeners remain highly skeptical whether she’ll follow through.
• When asked what advice she’d give a friend in her shoes, Angela says: be honest with your fiancé—a policy she herself hasn’t followed (16:23–16:31).
• The episode ends with the promise to check back with Angela in a few weeks (16:38–16:44).

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Notable Quotes & Memorable Moments (with Timestamps)

• “No, it wasn’t two. Sorry. It was three.” – Angela (00:31)
• “He gave me a diamond tennis bracelet from Tiffany’s… and for Christmas, I got a Wii with all the freaking accessories.” – Angela (03:39)
• “At the end of the night, he proposes with a freaking huge ring…” – Angela (04:01)
• “What do you think I said? …I said yes.” – Angela (05:01)
• “I wear his—the high school sweetheart ring, because it’s huge, and I just kind of take it off and put it in the ashtray every time I see my first fiancé.” – Angela (05:40)
• “You just like the celebration of you.” – Host (07:00)
• “You’re toying them like they’re catnip and you’re a cat.” – Host (09:49)
• “This time, at least most parties know about each other.” – Angela (12:07)
• “I want to marry my current fiancé because I love him.” – Angela (12:41)
• “Have you ever been married before?” “No.” – Host & Angela (13:06)
• “What is it? Caliente kiss? Is that what Bert calls me?” – Angela (11:21)
• “I would tell her to do the same thing I’m doing, except be honest with your current fiance.” – Angela, giving advice to a hypothetical friend (16:23)

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Key Timestamps

• 00:31 – Angela recounts her triple engagement history
• 03:39 – Lavish gifts and the birthday breakdown
• 05:01 – The high school sweetheart’s surprise proposal
• 07:00 – Hosts question Angela’s motives
• 09:49 – “You’re toying them like catnip”
• 11:21 – Angela jokes about her “moves”
• 12:07 – Admits overlapping engagements
• 16:23 – Angela gives (conflicted) advice
• 16:44 – Episode closes

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Tone & Style

• Playful, irreverent, genuinely bewildered by Angela’s audacity
• Hosts are both judgmental and amused—friendly ribbing mixed with real concern
• Angela herself is unapologetic, witty, and occasionally defiant (“This is Angela, the black widow here!”)

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For Listeners Who Missed the Episode

This episode of The Bert Show is a wild, funny, and occasionally exasperating look into the intertwining love lives of one memorable caller. If you enjoy real-life relationship drama, bold confessions, and sharp-tongued radio banter, this story of “the black widow’s” engagement entanglements is a must-listen—or at least a must-read summary!

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Transcript

[A]

The first show, way back before we left for Christmas break, we asked the question, who had been engaged to more than one person at the same time?

[B]

Mm.

[A]

And Angela called us up initially to talk about that, but then we got into a conversation about her and her boyfriend and their relationship, and she wanting to stick it out in the relationship until she got her presence right. Now, here's some of that conversation. Angela, you're on the voice disguiser. Were you engaged to two guys at the same time?

[C]

No, it wasn't two. Sorry. It was three.

[A]

Three.

[C]

Three guys at the same time. First guy. You know, high school sweethearts, we're gonna get married, yada, yada, yada. We get the engagement ring, and we set the date, started planning everything for four years later, after college. I wasn't ready for it then, so I wasn't like, we're not gonna last. Yada, y'. All, whatever. I'm doing my thing while I'm in college. Fall in love. My junior year, three years into our engagement, I still see my engaged boyfriend every holiday, every break, yada, yada, yada. So I fall in love with this guy junior year, and he asked me, and I was like, okay, so that's guy number two. Well, we set our marriage date for that summer. Okay. Well, the summer comes, and he gets this really great job opportunity, and we push it back to when I graduate, because he was a year older than me. Push it back to when I graduated from college. Well, he is away doing his thing. And immediately after graduating from college, I got this really great job that sends me abroad to England. And I'm in England for a year, and I fall in love with this guy, and he's like, yo, let's get married and everything. And so I'm like, why not? Let's go ahead and go for it.

[A]

All right, so that's the first part of the conversation. And the second part that you don't hear there is her telling us that she's in this relationship with a guy, and she's just sticking it out. She wants the Christmas presents.

[B]

Well, they're so close to the holidays.

[D]

Why not? I mean, he had already gone shopping. She was gonna save him the trip to return them.

[B]

Exactly.

[A]

It's a little hypocritical of us to come down on her, because I said in that certain window, you gotta stick it out.

[B]

That's true.

[A]

Like, if it's, like, after December 15th or something like that and you're not happy, you got to stick it out until January 1st.

[B]

Right? So because you don't well. And well, that was so that you would not hurt the feelings of the person that you were about to break up with. But in her case, it wasn't. She was concerned about hurting his feelings. She want to make sure that she got something. She got her goods before she left.

[A]

Hey, Angela.

[C]

Good morning, bro.

[A]

How are you?

[C]

Sorry about this morning.

[A]

That's okay. We got so late.

[C]

Okay. And one more thing. Am I on the voices? Kaiser?

[A]

You are.

[C]

Okay. Just checking. My baby's listening.

[B]

Your baby?

[A]

So you guys are still together?

[C]

Yeah. Oh, okay.

[E]

He must have given you something good.

[C]

Oh, my God, he did. He gave me. He gave me a diamond tennis bracelet from Tiffany's and he got me little diamond style tears. So I was really happy. That was my birthday, which is a couple days before Christmas. And then for Christmas I got a Wii with all the freaking accessories. And it was great. It was wonderful. But. Yes, let me tell you the story. So I had something for my rookies a couple days before Christmas. And we, during my birthday weekend, we sit down and we have this discussion. And he's like, baby, I sense that you're pulling away from me and I don't want to lose you. And I want to sit down and let's talk about what's wrong with you. Let's talk about this relationship. Put your trust in me. Don't leave me like you did the other guys. I'm different. I was like, okay, babe, sure. I sit down and I'm thinking to myself, can I be real with this guy? Can I actually get married? And I decide I can. And I take the relationship completely. And so I don't break up with him after Christmas like my plans were. But a couple days after that, my mom threw me this huge I'm turning 30 party. I mean, she outdid herself. She invited some of my high school buddies, some friends from college. I think some of my international friends even flew in for it. Well, my high school sweetheart found out about the party through one of my best friends and he flew in for my birthday party.

[D]

Really?

[C]

Yes. It was. It was so awesome. And we spent the whole night talking and catching up and all this great stuff. And at the end of the night, he proposed us with a freaking huge ring. Okay, the ring is huge.

[A]

Wait, wait, wait. I'm gonna back up for one second because wasn't. If I remember the story correctly, isn't the high school sweetheart one of the guys that you were engaged to at the same time as the other guys?

[C]

Yes, he was one. He was the one that I Also wanted to try it again with.

[B]

Right. She did tell us that this is the one that she still had feelings for.

[A]

Okay, so.

[D]

So your current sweetheart was not at this party?

[C]

Oh, no. My mom can't stand him, so he wasn't invited.

[A]

Okay.

[D]

That's how the high school boy got in.

[A]

All right, got access. And chronologically, here it goes. Conversation with current boyfriend, Christmas, whole bunch of gifts. And then the party.

[C]

No, no, it goes. Conversation with boyfriend, birthday, whole bunch of gifts.

[A]

Gotcha.

[C]

Then the party.

[A]

Got it.

[C]

Then proposal.

[A]

Okay.

[D]

Wow. And what'd you say?

[C]

What do you think I said? This is Angela, the black widow here.

[B]

Okay.

[E]

You said yes?

[C]

I said yes.

[A]

So this is the second time you've been engaged to this guy?

[C]

Yes, this is the second time. And you should have heard the proposal. He was like, I know we tried it before, but I still love you. You're the only one for me. Soulmate. Yeah. Womp, womp, womp. It was beautiful, guys. It was beautiful.

[A]

And the current has no idea of any. Does he know yet that you're engaged?

[C]

It depends on how savvy he is. If he's really good at being my baby, he knows that I'm talk about him now on the radio, but other than that, no, he's.

[E]

So this is the. This is the first time he's going to hear about it. It's broadcast on Q100.

[C]

Yeah, yeah.

[B]

Where's the ring? Where do you hide the ring he has?

[C]

I wear his. The high school sweetheart ring because it's huge, and I just kind of take it off and put it in the ashtray every time I see my. I guess, first fiance in the car ashtray? Yeah.

[B]

Okay. It's in your car. Okay.

[A]

I don't understand. Like. I mean, you seem so. The thing that I find so interesting about you is, you know, all of this is so wrong, yet you're so callous about it, and you really, like, can go from guy to guy and you really don't care.

[C]

Whoa, whoa, whoa. Wait. Wait a minute. Wait, wait, wait. First of all, I didn't go from guy to guy. He came to me. He came to me and he was. Cause we talked. My high school sweetheart, we talked the entire night. He was well aware that I wasn't engaged and set to be married in three months. He was willing to. You know, he was like, baby, you're making a mistake. Let's try it. And so if he knows that I'm already engaged and he's willing to wait for me to work it out, it is not my fault.

[D]

Now, was this more orchestrated from your mom than we even know about?

[E]

Yes, totally.

[F]

It could have been.

[C]

Because, like I said, he was out of the country, and I don't have information from him. He's in the military. But, you know, it makes sense. Cause he landed a couple days before my birthday, and he does talk to a lot of my friends a lot. So he could have just heard about it through them.

[A]

Don't you? The more we talk to you, the more I realize you just like. You like the celebration of you like. I'm not really sure this engagement is really gonna go anywhere, but. You like to get presents on Christmas. You like to have birthdays thrown for you. You like to get engagement rings. You like the whole process. You just like the celebration of you. Do you really love this guy?

[C]

I really love, I guess my current fiancee, the one I'm marrying in March. I really love him. Really do. I really want to marry him. But that's my high school sweetheart. I've loved him for so long. I'm not. It would be wrong for me to say, well, no, I'm not gonna entertain this because you're a couple months too late, you know?

[B]

Did you say March?

[F]

March?

[C]

Yeah.

[A]

Okay, I'm confused now. We're talking about so many guys now I got it all confused. So you just said that you're really in love with your current, but you're prepared to marry the ex high school sweetheart?

[C]

Yes.

[B]

Who are you marrying in March?

[C]

That's when our wedding date was set for the current.

[B]

With the current one?

[D]

Yes.

[C]

The one I was gonna break up with.

[D]

The Tiffany's bracelet one.

[C]

Yes.

[A]

Are you lying about all this?

[C]

Oh, dear. No.

[A]

So why wouldn't you just tell him?

[C]

Then?

[A]

The engagement is off and I'm gonna be with the ex.

[B]

Oh, that's silly, Bert. Because then she'd be cutting off some of her goods. The tennis bracelet cut off the engagement ring, and she's got another engagement ring.

[E]

Why would she end the celebration of her.

[D]

That's true.

[C]

You guys make me sound so bad. No, no, no. I mean, if you don't want us.

[E]

To make you sound bad, we'll take calls.

[C]

No, no, no, no, no. I mean, my current boyfriend. I mean, my current fiance. I told him. I was like, you know, I had this big birthday party. My ex was in town, and I wanted to hang out with him. He knows I'm hanging out. He just doesn't know. He asked me to marry him, and I'm gonna tell him. It's just that it Was the holiday time, and I couldn't find the right moment.

[A]

All right. Stephanie thinks you're making this whole thing up. Hey, Stephanie.

[C]

Hi.

[A]

Hey.

[F]

I have a girlfriend who is just like her. She is a narcissistic, delusional liar. Just crazy. There may be a little bit of truth to her story, but the rest of it is all embellishment. She's embellishing this story.

[A]

Angela, you promise you're not making any part of this up?

[C]

I promise I'm not making any of this up.

[E]

Why do you say. I'm curious to why she thinks that the same thing that applied to a friend applies to. To her.

[A]

I don't know. She's gone.

[C]

Hello? Where'd she go?

[A]

She's gone. I hung up on her accidentally. I thought she was just done with her point. Hold on. Good morning, Deborah. You're on Q100.

[C]

Hey, Bert.

[F]

How are you guys doing this morning?

[A]

Shaking our heads. How are you?

[C]

Great.

[F]

I think the girl is crazy.

[B]

Okay?

[C]

Loony.

[F]

And if she think that she's not doing anything wrong, that just, you know, seals my case. I mean, why would you not think you're doing something wrong? I mean, why would you think that? It's just their. I mean, they're doing everything wrong and you're just reaping the benefits. I think she's crazy.

[B]

Yeah.

[A]

You know, you're totally toying with these guys. I mean, you're. You're toying them like they're catnip and you're a cat.

[C]

Wait, no, no, no, because I'm. First of all, I'm not. Okay, the first three fiance's, when I was younger, that was all wrong. But this one is not. Like, I asked the guy to fly in for my birthday, and it's not like I told him to marry me and it's. I let him on.

[E]

You said yes.

[C]

You said yes That I was in. I had on my fiance's ring. He knew that.

[E]

But you said yes when he asked.

[C]

He asked in front of my entire. All my friends and family and nephews and nieces. What the hell was I. What the heck was I supposed to say?

[A]

No, no, they all knew that you were engaged to another guy.

[C]

Okay, but like, I'm still. There are still feelings there. And there is a. There are still feelings there that I would be wrong if I did not explore them before I walked down the aisle to another man.

[A]

Well, I have feelings for the girl I went out with in the seventh grade.

[E]

That's gonna be a fight later.

[A]

I'm not marrying the girl.

[B]

Well, you know, the people that hate her the worst are the people who can't get their boyfriends to. To ask them to marry him. Like our Birch show listener that's been married, dated the same guy for five years, and he still won't propose to her. And then every. I mean, I'm surprised that you can't go to the mall today and some random guy comes up and proposes to you. Like, what is it that you do that's different?

[C]

I'm a great gal. I mean, hate to blow my own point in, but I'm a nice person, I guess.

[D]

You got some sort of move. I need to learn something.

[C]

What is it? Caliente kiss? Is that what Bert calls me?

[A]

You got more than that.

[C]

That's what it is.

[A]

You got way more than that. Sarah, you're on Q100. Hey.

[C]

Hey.

[F]

When you're not that nice of a person, you wouldn't be leading both these guys on like that. But the thing is. And I used to be a lot like you, and I was engaged, like, six times before I actually got married, and now I'm happily divorced, but anyway, that's all beside the point. But the thing is, what you need to recognize is that this guy, the one from high school, he is disrespecting, like you and your current fiance and himself by just walking in and saying, oh, no, marry me instead, and it's just all a big mess. You're getting yourself into nothing but trouble, so just back away from Mr. High School.

[A]

I mean, this is the second time now that you've been engaged to multiple people at the same time.

[C]

This time, at least most parties know about each other.

[D]

Most parties know about it.

[A]

Well, you said he doesn't know about.

[B]

Who knows about who.

[C]

Okay, the high school sweetheart knows about my current fiance.

[A]

Yeah, but the current doesn't know about the high school sweetheart.

[C]

He doesn't know that I'm engaged. No, but if he does know that, we spend quite a bit of time together.

[B]

And does the boy, the high school dude, know that the current you are engaged to him?

[C]

He knows. What? I mean, he knows. He's seen my wedding dress. He knows the date. He knows everything.

[D]

So who are you gonna marry?

[E]

Neither of them.

[B]

Nobody.

[C]

I want to marry my current fiance because I love him.

[D]

No. Who are you going to marry?

[B]

Neither.

[E]

We should have Hoss ask for a.

[D]

Seriously, Are you gonna actually be able to walk down the aisle with either one of them?

[C]

I want to. One of them?

[D]

Which one? You just want to clone the good parts of both of them, meld them together, and then that's the guy you'll marry.

[A]

Have you ever been married before?

[C]

No. No, I haven't.

[A]

So you've never gone through the, you know, the celebration of a wedding day or anything? So that's not. The idea of. It is intoxicating to you?

[C]

Actually, the idea is kind of overwhelming.

[A]

Well, yeah, because you've done it nine times.

[B]

Well. And you have to stay there. Like, you have to stay with the same guy once you go through the.

[C]

Ceremony and you got to stay faithful for the rest of your life.

[B]

Yeah.

[A]

You think. You think you have that in you?

[C]

I'm going to marry my current fiance.

[F]

I just.

[C]

I. It would be wrong of me to go down the aisle and say yes to this man, knowing and wonder what could have been or what would have happened if.

[A]

So are you going to pursue a relationship with the ex through the engagement and then just get married to the current?

[C]

Not all the way through the engagement. We need some time to get to know me, because I haven't seen this man in about six years. I want to get a chance to get to know him, see what he's all about.

[B]

Well, that's good.

[C]

Say again?

[B]

Yeah, you take before. Yeah, before you get to know him. It's. I mean, perfect. Perfect plan.

[C]

Yeah, it is.

[A]

It's so simple. Hey, Jennifer, you're on Q100.

[C]

Hey, I think she's a gold digger. What the heck? What the heck? What the. Why do I need to. If you want to, then that would be fine. But you don't need to sit there and say engaged. Engaged means married for the rest of your life. You're taking marriage as a joke? How am I taking it? Okay, because obviously you're sitting here engaged.

[F]

To three different guys. How is that not a joke?

[C]

And the joke is on you because you're the idiot doing it. Much younger. I admitted that one was wrong. Okay?

[F]

But this one is just as wrong as the one before, because you are still sitting here engaged to two separate men.

[A]

Angela, you can honestly take a look at your own situation right now, and you can say, I'm not doing anything wrong.

[C]

It's not like I called up my high school sweetheart and said, hey, come in and ask me to marry you because I need another engagement ring. I didn't do that. I didn't invite him to the party. I didn't ask him to marry me. I did not do anything wrong because I'm not out there.

[E]

You said yes. You said yes.

[A]

You already engaged me.

[E]

The proper answer. The answer Is, I'm sorry. I'm engaged to someone else.

[C]

Okay, so suppose I would have said no, right?

[A]

Yeah.

[C]

And my wedding day comes, right? And I am walking down the aisle and I see my high school sweetheart in the audience, and all of a sudden I am filled with, oh, my God, what would have happened?

[E]

That's great.

[C]

After I get married and supposed to be faithful to the man for the rest of my life, I cheat. Because I've always. I would have wondered what happened.

[E]

Hey, black widow, listen, the proper answer is no. And then you go back to the other guy if you have doubts, and you say, hey, we gotta call off our engagement because I gotta explore some things with a past flame who's come into my life and maybe wants to rekindle some things.

[A]

But, you know, you'd lose the guy, so you can't do that, right?

[C]

I don't think I would lose him, would I?

[E]

I hope so.

[A]

Well, there must be a reason why you didn't tell him.

[C]

Because he wouldn't understand. And he wouldn't say yes before. I mean, before even acknowledging Lord Amber.

[A]

All right, we're gonna have to follow up with you.

[B]

Wow.

[D]

I want to find out what advice you would give to a friend of yours if she were going through the same situation.

[C]

I would tell her to do the same thing I'm doing, except be honest with your current fiance. Let him know what play.

[A]

But you haven't done that.

[C]

I wasn't giving the advice to myself, though. You said my best friend.

[A]

Okay, so it'll be different for you. All right. We'll check back with you in a couple of weeks, see where your head's at.

[B]

Okay.

[C]

All right.

[A]

All right. Bye.

[C]

Bye.

[A]

The bird show.