Vault: What was your extreme obstacle in your relationship?

Summary

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The Bert Show

Episode Title: Vault: What Was Your Extreme Obstacle in Your Relationship?
Air Date: June 30, 2026

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Episode Overview

This episode of The Bert Show centers around the theme of extreme relationship obstacles. Listeners call in and anonymously share the hardest challenge their relationship has faced—be it infidelity, financial secrets, or shocking betrayals—without initially revealing whether their relationship survived the ordeal. The show’s hosts and co-hosts then try to guess the outcome before the caller reveals the truth. The episode balances real-life drama with characteristic humor as the crew discusses big, messy, and unexpected relationship hurdles.

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Key Discussion Points & Insights

Introduction to the Game: "Extreme Obstacle"

• [00:59] Host ("Bird") introduces the concept: Listeners describe their relationship’s biggest challenge—without saying if they survived it—while the hosts guess the outcome.
• Celebrity examples (like Tiger Woods and Kobe Bryant) are used for context: extreme cheating scandals and whether such relationships can survive infidelity and public shame.
  • Quote: "If I had Tiger woods on the line right now... I had a little problem with fidelity in my relationship and I ended up cheating on my wife 17 times. Did my relationship survive or not?" — Host (01:07)
• The tone is playful, candid, and sometimes surprised at the capacity for forgiveness or endurance.

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Caller Stories

1. Abby – Cheated on Fiancé with Her Best Friend

• [03:07] Abby confesses to a month-long affair (10 times) with her best guy friend while engaged.
• Hosts take turns guessing the outcome:
  • Most say the relationship could not have survived.
  • Co-host 2: "I say they got married." (04:01)
• Outcome: Abby reveals they're still engaged. Her fiancé forgave her, though trust was tested but is now “gone.”
  • Quote: "Yeah, we’re still engaged. He forgave me." — Abby (04:10)
• Hosts react with a mix of skepticism and surprise.
  • Notable moment: Co-hosts challenge whether trust truly ever “goes away.” (04:45)

2. Denise – Pregnancy Amidst a Long-Term Lesbian Relationship

• [04:57] Denise, after nine years in a relationship with her girlfriend, had a one-night stand with a man, got pregnant, and kept the baby.
• Hosts speculate:
  • Majority think the relationship ended, but a few optimistically guess survival and co-parenting.
• Outcome: Denise says the relationship survived; both women are raising their 18-month-old son together. The baby’s father is absent.
  • Quote: "The relationship survived. Our son is 18 months old..." — Denise (05:57)
• Denise explains it was a “weak moment” during relationship difficulties.
• Humor ensues as the crew ponders how Denise was convinced to sleep with the man after a lifetime of lesbian identity (06:30–07:00).

3. Leslie – Cheated on by Husband with Her “Nemesis”

• [07:52] Leslie’s husband had an affair with her arch enemy from junior high and allegedly got her pregnant.
• All hosts unanimously vote no survival.
• Outcome: Turns out the nemesis lied about the pregnancy. Leslie forgave her husband, and they remain married.
  • Quote: "She made fake doctor’s papers and all sorts of crazy stuff... we've been married for three more years." — Leslie (08:31)
• Notable moment: Hosts discuss real-life nemesis stories, using Stacy and “Jamie Van Sickle” as a sidebar example (09:09).

4. Sheila (misheard as “Shiloh”) – Fiancé’s $130,000 Debt Revelation

• [09:47] Sheila’s fiancé admits, the night before their wedding, to $130,000 in undisclosed debt (mostly credit cards).
• Hosts split on whether they married; some anticipate a breakup, others commitment.
• Outcome: Sheila says they married, and are approaching their 10-year anniversary, still paying off the debt.
  • Quote: "May 21st will be our 10 year anniversary." — Sheila (10:28)
• Sheila’s practical approach to financial adversity is praised (10:41).

5. Becky – Years of Lies, Cheating, and Addiction

• [11:00] Becky was married for nine years, with two kids. Husband cheated for three years and struggled with drugs and alcohol.
• Hosts suspect the relationship ended. Becky confirms: “It did survive [for a while]. And then I collected all my evidence... and got out.”
  • Quote: "There was a brief survival period before I killed it." — Host, joking (11:54)
• The group reflects on emotional endurance and finally choosing to leave.

6. Christy – Long Relationship, Hidden Addiction

• [12:23] Christy, after 16 years with her partner, discovers he’s been using drugs for 10 years and has gone to rehab five times.
• Some hope for recovery, others expect a split.
• Outcome: They’re still together, though he isn't sober. Christy has support from friends, not Al Anon.
• Quote: "He’s still struggling, but we are still together..." — Christy (13:01)
• Hosts show empathy for the ongoing fight and differentiate between perseverance and acceptance.

7. Terry – Married Girlfriend Despite Being Gay

• [13:26] Terry calls in, revealing that 30 years ago, he married his high school girlfriend though both knew he was gay. They had a son.
• Big reveal: They are no longer married—Terry has been in a same-sex relationship for 25 years and is very happy.
  • Quote: "If you're gay and you know it, don't marry a woman." — Terry (14:26)
• Hosts close the segment reiterating Terry's advice with laughter and appreciation for honesty (14:34).

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Notable Quotes & Moments (with Timestamps)

• "If I had Tiger woods on the line right now... I had a little problem with fidelity in my relationship and I ended up cheating on my wife 17 times. Did my relationship survive or not?" — Host (01:07)
• "Yeah, we’re still engaged. He forgave me." — Abby (04:10)
• On trust issues after infidelity:
  "It’ll never go away. But yeah." — Abby (04:43)
• "The relationship survived. Our son is 18 months old..." — Denise (05:57)
• "May 21st will be our 10 year anniversary." — Sheila (10:28)
• "There was a brief survival period before I killed it." — Host, joking about Becky’s story (11:54)
• "If you're gay and you know it, don't marry a woman." — Terry (14:26)
• "Everybody’s... Every guy’s got a lesbian who will give him one chance." — Co-host 1 (14:38)

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Segment Timestamps

• Intro & Rules Explanation: [00:59] – [02:56]
• Caller 1 (Abby): [03:07] – [04:46]
• Caller 2 (Denise): [04:57] – [07:04]
• Caller 3 (Leslie): [07:50] – [08:55]
• Caller 4 (Sheila): [09:38] – [10:43]
• Caller 5 (Becky): [10:53] – [11:54]
• Caller 6 (Christy): [12:23] – [13:22]
• Caller 7 (Terry): [13:26] – [14:38]
• Conclusion/Wrap: [14:38] – [15:11]

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Language & Tone

• The tone is lighthearted, direct, and often comedic, but respectful of callers’ experiences.
• Hosts use humor to soften heavy topics, and listeners provide raw, honest glimpses into real relationship turmoil and resilience.
• The game format brings both fun and insight as the team guesses outcomes, sometimes leading to surprising revelations about forgiveness, endurance, and personal boundaries.

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Summary

This episode is a rollercoaster of relationship challenges, revealing the unimaginable obstacles some couples survive—while others rightfully end. Whether it’s infidelity before the wedding, secret children, life-altering debt, addiction, or mismatched sexuality, The Bert Show’s crew and their callers explore the extremes of love, loyalty, and human folly. The format is engaging and informal, giving listeners both laughter and food for thought on the resilience (and limits) of relationships.

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Transcript

[Narrator]

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[Lady Luck]

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[Host (possibly 'Bird')]

Listen, it's the vert show, all right? I would like to do a little game with you guys called Extreme Obstacle, all right? If you have been in a relationship, maybe even your marriage, right, and you've gone through a crazy extreme obstacle in your relationship, I want you to call us right now, 404741 Q100, and you tell us what that Extreme Obstacle was. Don't tell us if the relationship survived or not, okay? We're gonna try to guess if you guys made it or not. For instance, like if I had Tiger woods on the line right now, right? 404-741-Q100. Tiger would call up and go, you guys, I'll tell you what, I had a little problem with fidelity in my relationship and I ended up cheating on my wife 17 times. 17 times. Did my relationship survive or not? Then we would go around the room and we would try to guess if you guys made it. Because in looking at their relationship, nobody would say that they've made it. But there were pictures this morning came out. They're kissing and stuff, right?

[Co-host 1]

Yeah.

[Co-host 2]

They were in Windermere, Florida, which is where their home is in their neighborhood. And apparently they were spotted hugging and kissing each other. And sources close to the family say that they are definitely working it out and he is winning her back over again.

[Host (possibly 'Bird')]

Now this could be anything, okay? The guy I was dating, I found out was sleeping with my father. Did my relationship survive or not? Then we guessed. And this doesn't have to always be, you know, like you guys survived. It could be a breakup also, okay?

[Co-host 3]

But just don't tell us.

[Host (possibly 'Bird')]

Just don't tell us.

[Co-host 3]

Right.

[Host (possibly 'Bird')]

I'm trying to think what other actor or athlete we could use as an example.

[Co-host 4]

Kobe.

[Host (possibly 'Bird')]

Yeah, there you go.

[Co-host 4]

Yeah, because didn't he have an affair on his wife?

[Co-host 3]

Assault.

[Host (possibly 'Bird')]

Assault.

[Co-host 3]

Allegedly.

[Host (possibly 'Bird')]

So we'd get the details of the Kobe situation and we'd probably all say there's no way that that survived.

[Co-host 1]

Well, then we get all the details, including the ring, the size of my parents, one car garage.

[Co-host 2]

That's true.

[Host (possibly 'Bird')]

404741, Q100. Good morning, Abby. You're on the voice disguiser. And of course we can put all you guys on the voice disguiser. What's up, Abby?

[Caller/Guest]

Hey.

[Host (possibly 'Bird')]

All right, Abby, just give us the details and don't tell us if it survived or not.

[Caller/Guest]

Okay. I cheated on my fiance we. With one of my best friends. And like a whole month of it happened.

[Co-host 1]

So you had a 30 day affair with your best guy friend?

[Caller/Guest]

Yeah, my best guy friend.

[Co-host 1]

While you were engaged?

[Caller/Guest]

Yes.

[Host (possibly 'Bird')]

And you confessed this to your fiance?

[Caller/Guest]

Confessed it.

[Host (possibly 'Bird')]

Okay. And how many times did you have sex with this guy?

[Spinquest Promo Announcer]

10.

[Caller/Guest]

Yes.

[Co-host 4]

And how long was the relationship up to this point? Up, up to this point?

[Caller/Guest]

The fiance. Three years.

[Host (possibly 'Bird')]

Three years.

[Co-host 2]

Three years.

[Host (possibly 'Bird')]

All right. Cheated with one dude Best friend 10 times in a month before they were gonna get married.

[Co-host 4]

I'm going, no way.

[Host (possibly 'Bird')]

You say no, I say no.

[Co-host 2]

I say they got married.

[Co-host 1]

No way.

[Host (possibly 'Bird')]

I'm going with no way. Did you guys get married?

[Caller/Guest]

You wanna know now? Yeah, we're still engaged. He forgave me.

[Co-host 2]

No, still engaged. When's your wedding day?

[Caller/Guest]

In May.

[Co-host 3]

Is the best friend still around?

[Caller/Guest]

I chose to not keep him around.

[Co-host 3]

That's the only reason you're engaged?

[Co-host 2]

Wow.

[Host (possibly 'Bird')]

So he stuck around. Trust issues. Gone now.

[Caller/Guest]

The trust issue was there for a little bit.

[Caller (Taylor)]

It's.

[Caller/Guest]

It's gone now, though.

[Co-host 2]

I mean, it'll take time of course, but it's not. It never.

[Host (possibly 'Bird')]

It never goes away.

[Caller/Guest]

It'll never go away. But yeah.

[Host (possibly 'Bird')]

Okay, Abby, thank you.

[Caller/Guest]

Thank you.

[Co-host 3]

Good luck in that marriage.

[Host (possibly 'Bird')]

That one survived.

[Co-host 4]

Wow.

[Host (possibly 'Bird')]

At least now. Okay.

[Co-host 2]

All right.

[Host (possibly 'Bird')]

Denise wants to be on the voice disguiser. 404741, Q100. Hey, Denise.

[Caller/Guest]

Hi.

[Host (possibly 'Bird')]

All right, give us the extreme obstacle your relationship went through. Then we'll try to guess if it survived or not. Then you tell us the result. Okay?

[Caller/Guest]

Okay.

[Host (possibly 'Bird')]

All right, go for it.

[Caller/Guest]

My, at the time, nine year relationship with my girlfriend. I had an affair with a man, got pregnant and kept the baby.

[Co-host 1]

And you were in a relationship with a woman at the time?

[Caller/Guest]

Yes.

[Co-host 1]

For almost a decade?

[Caller/Guest]

Yes.

[Caller (Terry)]

Wow.

[Host (possibly 'Bird')]

I would say the relationship did not survive.

[Co-host 4]

I'm gonna go with no.

[Co-host 3]

Hell, no.

[Co-host 2]

I'm going with yes. You and your girlfriend are raising the baby together.

[Co-host 1]

I'm gonna go with yes. You're still together, and Melissa will use this model to have her baby.

[Co-host 3]

Right? You keep trying, Jeff.

[Co-host 2]

Keep trying.

[Co-host 3]

I'm right here on that door.

[Co-host 1]

Listen, I got a trombone in your hands. And that's where it starts.

[Host (possibly 'Bird')]

Denise, did the relationship survive?

[Caller/Guest]

The relationship survived. Our son is 18 months old, and

[Co-host 2]

you and the girl are together raising the kid.

[Caller/Guest]

We are together.

[Co-host 1]

And where's dude, where's daddy?

[Co-host 2]

Where's the baby daddy?

[Caller/Guest]

God only knows, really.

[Host (possibly 'Bird')]

And you were. You were lifetime lesbian up until that point?

[Caller/Guest]

Yes.

[Host (possibly 'Bird')]

And had one night with this guy?

[Caller/Guest]

Yes.

[Co-host 1]

How'd you do it? How'd he do it? Like, what did he say?

[Co-host 3]

Oh, no.

[Co-host 4]

Can you hold.

[Co-host 1]

Can I talk to you off the air?

[Host (possibly 'Bird')]

Yeah. Like, for. I mean, your whole life, you held out. So what did this guy say that you, like. You know what? I'm gonna give this try one time.

[Co-host 3]

Thank you so much for all lesbians out, honey.

[Co-host 1]

No, seriously, how did it happen that one time?

[Host (possibly 'Bird')]

Why'd you choose him there?

[Caller/Guest]

Well, it wasn't. It wasn't like that. It was just. There had been some other circumstances in the relationship that caused me to have a weak moment, and he caught me at the right time with a guy.

[Co-host 3]

Yeah.

[Co-host 2]

Wow.

[Co-host 4]

Yeah. I just can't.

[Host (possibly 'Bird')]

He hit the lottery. He hit the lottery.

[Co-host 1]

Are you feeling weak or strong today, Carter?

[Lady Luck]

Yeah.

[Co-host 3]

These stories do kind of irritate me because. Yeah, I wouldn't. Yeah, there's. I could be weak. There's never a moment in which a guy could be in bed with me.

[Host (possibly 'Bird')]

This is for a guy. This is a. This is a really moment. Like, it would be like you finally saying yes to Jeff and him going, really?

[Co-host 3]

Yeah.

[Co-host 1]

I would ask you, while it's happening, are you sure you want to be doing this? Are you 1000% positive that we all should be here?

[Host (possibly 'Bird')]

I wouldn't even give you a millisecond to think about it again as soon as you said yes. Right on it. All right, Leslie, you tell us the extreme obstacle your relationship went through. Just don't tell us if the relationship survived until we ask you.

[Caller/Guest]

Okay?

[Host (possibly 'Bird')]

Okay.

[Caller/Guest]

My husband cheated on me with my worst enemy and got her pregnant.

[Co-host 1]

Did not survive. No way.

[Host (possibly 'Bird')]

Oh, now, was this the worst enemy from, like. I mean, it started in junior high and went through high school, or is this adult Enemy.

[Caller/Guest]

It started junior high. Went through high school with your adults.

[Co-host 2]

Oh, I saw Nemesis. Okay, Nemesis.

[Host (possibly 'Bird')]

Lifetime nemesis.

[Co-host 1]

I think a woman could survive her husband having an affair with her best friend over having an affair with her arch enemy.

[Host (possibly 'Bird')]

So you say, no, it did not survive. No way, Jen.

[Co-host 2]

I say you left him and you did. His best friend, Melissa.

[Co-host 3]

I can tell by your tone, no, it did not work.

[Co-host 4]

No way.

[Host (possibly 'Bird')]

I say no way.

[Caller/Guest]

Actually, we found out a couple months later that she was lying and that it was just a one time thing. So I forgave him. And we've been married for three more years. What?

[Co-host 3]

I suck at this game.

[Co-host 1]

Did she target your husband because you guys are enemies?

[Caller/Guest]

I don't think so. She like made fake doctor's papers and all sorts of crazy stuff. So yeah, it was. It was fun.

[Host (possibly 'Bird')]

My wife Stacy has a nemesis in her little itty bitty town up there in Pennsylvania that was just bullying Stacy for like three years. I mean, it was really, really bad. And I know her. Jamie Van Sickle and Stacy.

[Co-host 3]

What were their names?

[Co-host 2]

Jamie Van Claris.

[Host (possibly 'Bird')]

Stacy hates her as much when she talks about her.

[Co-host 1]

She hates her today.

[Host (possibly 'Bird')]

It happened yesterday.

[Co-host 4]

Really?

[Spinquest Promo Announcer]

Yes.

[Co-host 3]

The fact that you just said her name on the air. Stacy threw something.

[Co-host 2]

I can't believe they hit each other.

[Caller/Guest]

What's her last name?

[Host (possibly 'Bird')]

Van Sickle.

[Co-host 4]

Van Sickle.

[Co-host 3]

Yankee names.

[Host (possibly 'Bird')]

Shiloh doesn't need to be on the Voice Disguiser. Go ahead. Tell us about the extreme obstacle.

[Caller/Guest]

Oh, it's Sheila.

[Host (possibly 'Bird')]

Oh, Sheila. Hey, Sheila. You don't need to be on the Voice Disguiser.

[Caller (Taylor)]

No, that's all right.

[Host (possibly 'Bird')]

Okay, Taylor, just call her Shiloh.

[Caller (Taylor)]

Okay. The day before I was supposed to get married, my fiance sat me down in the middle of our floor and told me that he was $130,000 in debt. And I had no idea.

[Host (possibly 'Bird')]

The night before you got married?

[Caller (Taylor)]

The night before I was supposed to get married, Invitations were sent, wedding was set.

[Co-host 1]

Everything was this like cash debt or is this like mortgages and stuff?

[Caller (Taylor)]

Like credit card debt?

[Co-host 3]

Oh, damn.

[Narrator]

Dang.

[Host (possibly 'Bird')]

You went through with it. You married him, Wendy.

[Co-host 4]

No, she didn't. No, no.

[Co-host 3]

Yes.

[Co-host 1]

Yes, she did.

[Co-host 2]

Yes, you married him.

[Host (possibly 'Bird')]

Go ahead.

[Caller/Guest]

You want me to say now?

[Host (possibly 'Bird')]

Yes.

[Caller (Taylor)]

May 21st will be our 10 year anniversary.

[Spin Quest Announcer]

Wow.

[Co-host 1]

How long until you pay off that debt?

[Caller (Taylor)]

A long time.

[Co-host 1]

Still working on it, huh?

[Caller (Taylor)]

We're still working on it yet, but it is very close to being paid off.

[Co-host 2]

Good for you. That's amazing.

[Co-host 1]

You know, we give $1,000 away at 7:15 every day. Just saying.

[Co-host 4]

Wow, that's A lot to take on.

[Host (possibly 'Bird')]

Here is Becky. Good morning, Becky.

[Caller/Guest]

Good morning.

[Host (possibly 'Bird')]

How are you?

[Caller/Guest]

I'm okay.

[Host (possibly 'Bird')]

All right. Extreme obstacle.

[Caller/Guest]

Extreme. Okay, well, let's see. Married for nine years and we had two kids together. He was cheating on me for about three of those nine years. As well as drugs mixed in with it and some alcohol.

[Host (possibly 'Bird')]

Drugs, Alcohol. Affair for you say three years?

[Caller/Guest]

About three years. He's having the affair. Yeah.

[Host (possibly 'Bird')]

Okay. Did the relationship survive, Wendy?

[Co-host 4]

No. Her tone makes me say no.

[Co-host 3]

No.

[Co-host 4]

Nope.

[Co-host 1]

I'm basing it on her tone too.

[Caller/Guest]

Well, it did survive. And then I collected all my evidence and took some of his money and got out.

[Host (possibly 'Bird')]

So it did not survive.

[Co-host 1]

It did not survive.

[Caller/Guest]

And I said, okay, you can have it right back.

[Co-host 1]

It did survive until the divorce was finalized. Then it no longer survived.

[Co-host 2]

Then it was finally done.

[Host (possibly 'Bird')]

There was a brief survival period before I killed it.

[Co-host 1]

He survived until I wrapped my arms around his neck and choked the life out of him. Then he was no longer a survivor.

[Host (possibly 'Bird')]

This is all based on the whole Tiger woods thing, man. The fact that he had all these affairs and they were taken. A photo was taken yesterday with them kissing. That he's gonna survive this? No way.

[Co-host 3]

Stupid. I just see Elon, like, oh, my God. Anyway, just. I can't believe she's doing this to herself.

[Host (possibly 'Bird')]

Hey, Christy.

[Caller/Guest]

Hey.

[Lady Luck]

Hi.

[Co-host 4]

Hi.

[Caller/Guest]

I have been in a relationship. We've had like a 16 year relationship, and of 10 of those years, I found out he was using drugs and I had no idea. I'm a little naive, I guess. And he's been to rehab like five

[Co-host 4]

times during your relationship?

[Caller/Guest]

Uh huh.

[Host (possibly 'Bird')]

He's been a rehab five times.

[Co-host 2]

I say that he's sober now and you guys have made it.

[Host (possibly 'Bird')]

Melissa, no. Yes, Jeff.

[Co-host 1]

I'm saying yes just because every one of them's yes.

[Host (possibly 'Bird')]

I'm gonna go with yes. It made it.

[Caller/Guest]

Yeah. Well, he's still struggling, but we are

[Co-host 2]

still together, so he's not sober.

[Co-host 3]

Wow.

[Caller/Guest]

Yeah.

[Co-host 2]

Are you an Al Anon?

[Caller/Guest]

No. I tried it, but I didn't work for you. It didn't work for me, but I have a lot of, you know, support friends that have been through similar situations that I. That I talked to. So, yeah.

[Host (possibly 'Bird')]

Okay. I'm not judging. All right, thank you. And here, we'll end this one with Terry here. Hey, Terry.

[Caller (Terry)]

How you doing, guys?

[Host (possibly 'Bird')]

Okay, you're on the voice disguiser. Go for it.

[Caller (Terry)]

Love the show. Love the show. Just wanted to add my comments. 30 years ago, I married my childhood high school girlfriend, even though both of us knew that I was gay.

[Co-host 3]

Want us to know if it survived or not.

[Caller (Terry)]

Well, hold on, hold on, hold on, hold on.

[Co-host 2]

He married his childhood high school girlfriend and they both knew at the time they got married that he was gay.

[Co-host 3]

Right, and you said that was 30 years ago.

[Caller (Terry)]

30 years ago.

[Co-host 3]

I say.

[Host (possibly 'Bird')]

No, no, no.

[Co-host 2]

I say you're so married.

[Caller (Terry)]

And to add to the mix, I have a 30 year old son.

[Co-host 2]

Okay, my guess is that you're married.

[Caller (Terry)]

We are not married anymore. And I've been in the same relationship with the Same guy for 25 years. Blissfully happy, really. Let me just add to that. If you're gay and you know it, don't marry a woman.

[Host (possibly 'Bird')]

If you've. If you've learned nothing from the show today, this is what you need to take away from it. Terry, one more time, your advice.

[Caller (Terry)]

Don't get married. If you know you're gay, don't marry someone of the opposite sex.

[Co-host 1]

Well, and what I've taken away from it is. Yeah, every. Everybody's. Every guy's got a lesbian who will give him one chance.

[Host (possibly 'Bird')]

This is the Bird show.

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