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Show Host
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Phil
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Show Host
Offers may vary.
Phil
Visit albertsons or safeway.com for more details.
Show Host
The first show Melissa Carter for those that are listening for the first time, or those that might have just caught Penelope last time, who is she and why have we been talking to her for weeks now? Because she has told us she's clueless about dating, Right?
Melissa Carter
And that's exactly why she called. Because she said, you know what? In any other realm of my life, I do fine, I'm confident, I'm social, but when it comes to dating and guys that I really like, then I lose all cool and I don't know what to do. And so she said that there was a guy in her office this summer that she's interning with and his name is Ian. And she said that she really wants this guy, but she has no clue on how to get him. So we called it how to get the guy. And that's what we were going to help Penelope do. So she agreed that she would not do anything other than what we tell her to do, the suggestions we make. And she's done that over the past few weeks and things have worked. We've suggested when to talk to Ian, when not to talk to Ian, how to act, what to say, what to do. And so we even had Phil at one point go and take her out for lunch so that Ian could see another guy take her out to lunch because we knew that that would get him kind of pumped up, his, you know, competitive streak pumped up and it worked. So after that happened, he asked Penelope out for a date this weekend. This past weekend, yes. And they had a date in Athens, but unfortunately, she was all ramped up. This was the first date. It was going to be exciting, and. And then it didn't go so well.
Show Host
All right, so if you missed the last time that we talked to Penelope, here's about 90 seconds of the conversation to truly get you caught up. So you said you were going to give him the cold shoulder. Birch show listening community said, look, this is the way you got to go. You asked us for advice, so you have to take it. And they said, after hearing that this guy disrespected you the way that he did, by not calling back, you had to show him how angry you are. So for 24 hours, you were supposed to give him the cold shoulder.
Penelope
He got it, and he came over to apologize, and he said, oh, you know, I'm really, really sorry. My ex girlfriend and I had, like, a lot of, you know, water under the bridge. There was a lot that we had to let out, and you didn't deserve that, and I'm really sorry for the way I treated you. So he said, please. So he begged for another chance. Please let me make it up to you, because I'm not like this. I'm really sorry.
Show Host
Does he define what's going on with the ex?
Penelope
Well, he said that it was over before he got to say goodbye, and they never really got to talk about anything, and that there was just a lot of anger that he had that he had, and he just lashed out.
Show Host
All right, so what is the next step here? Does she give him the cold shoulder for four days? Is it two days? Does she go through the weekend? Adam, go ahead. You're on the Birch Show.
Penelope
She needs Phil to go back over there, and that's just going to make him realize that he ain't got her yet and she's still willing to date other people, which will make him fight a little bit harder.
Show Host
You're good with all that.
Penelope
I should just go out with Phil.
Show Host
Which was the suggestion to go out with Phil again to get Ian's interest up. So, Phil, did you guys have that date?
Phil
No, we did not.
Adam
Why?
Phil
Here's what happened yesterday. I called her because the first time we met up for lunch, it was probably about 1245 ish, and I was running not.
Show Host
I was.
Phil
I wasn't even running late. I just want to call, make sure we're still on the same time schedule and time frame called the first time, no answer. You know, no Worries. Gave it about another. Left her message, called her back about 10 minutes later. Hey, Penelope, it's Phil. I'm getting ready to head up that direction. Just want to make sure we're still on. Want to make sure we're good to go. Still no answer. Then I called her office and left a message at her desk and left her another message and say, hey, Penelope, it's Phil. Are we still getting together today? Just need to know what's going on. Give me a call back. And I left her three separate messages. Two on her cell phone and then one on her office phone. Probably all within a span of about 30, 35 minutes. And never heard back from her once.
Adam
And are all of your 14 girlfriends mad about that?
Phil
They love it. And so I never heard back from her, so I wasn't gonna waste my time and go up there and. And, you know, because she. She doesn't work super close to the station. I had other stuff I had to do, so I was just gonna sit around and wait. And I gave her a window until about 2:00', clock, 2:15. And I never heard from her, so I just gave up on her.
Show Host
She may have a perfectly good excuse. Hey, Penelope.
Penelope
Hi, guys.
Show Host
Hey. Part of the plan here was that you were gonna go out with Phil again. Ian the intern would see you in the office with Phil again, get jealous, kind of jumpstart his interest even more. What happened?
Penelope
Well, as far as I'm concerned, that Phil never showed up. I told Ian that I had a date for lunch and Phil never showed up.
Phil
I called you numerous times. I never heard back from you. I mean, I was ready to go.
Show Host
You sure you had the right number and all?
Phil
Yeah, her voicemail. I've talked to it before. I even got her right voicemail at her office. Her desk, office phone.
Penelope
As far as I was concerned, you didn't show up. I didn't get any calls. I wasn't even looking for the phone. I was looking for. For you.
Phil
Did you not. Did you not get any of my voicemails yesterday? I left you two on your cell and one in your office at the.
Penelope
End of the day until I actually checked them. But I was waiting out the window looking for you. I was freaking out because I told Ian that we had a date. So I was humiliated in front of Ian when you just didn't show up.
Melissa Carter
All right, Penelope, hold on a second. Despite the miscommunication between you and Phil, why did you even tell Ian you had a date?
Penelope
What do you mean, why did I tell him that?
Melissa Carter
Because you were supposed to give him.
Penelope
The cold check me out to lunch. I told him I had a date.
Show Host
Who took you out to lunch?
Adam
He asked her out to lunch.
Penelope
I was doing for lunch. I told him I had. I had plans.
Veronica
And then. And then Phil stood you up.
Phil
I didn't.
Penelope
Yep.
Phil
I didn't stand you up. You have my number, too. How come you didn't call me?
Penelope
Oh, I didn't have my. My. My phone was all acting weird. It was just acting weird all day.
Show Host
Something doesn't smell right.
Penelope
Yeah, I had a weird day. So you guys got to help me get this guy, because I'm. It's not working out.
Show Host
Wait, we gotta back up for a second. Swear on your. On your water pipe that you weren't ditching.
Veronica
It's not a bong.
Show Host
That you weren't ditching Phil.
Penelope
Oh, I wasn't ditching Phil at all.
Show Host
Okay.
Penelope
No, I thought I was ditched, but it was. I say miscommunication. Fine. That's fine.
Show Host
Okay.
Penelope
Just fine. Just fine.
Adam
So when we told you to give him the cold shoulder. Right. What happened? Like, I'm confused on how he approached you to ask for lunch, because the.
Show Host
Last time we talked to you, he said something about, I apologize. I apologize about that. And you said, I need a couple of days to think about things. Just basically leave me alone for a couple of days. We'll check back at the end of the week type thing.
Penelope
Yeah. And he said, so, what are you doing for lunch today? He kept trying to be nice and kind. He came up to me, and weren't.
Adam
You supposed to say, dude, I need a couple days?
Penelope
Yeah, well, I said I had plans for lunch.
Melissa Carter
Well, wait a second. Okay, that happened yesterday. So up until. Yeah, so up until yesterday, from the time that you talked to us, then how have you given him the cold shoulder? Because I think what Jen's asking is, how did he feel comfortable enough to just randomly come up to you and say, I want to go to lunch to talk.
Penelope
He said we should talk. Do you want to go to lunch with me?
Show Host
That doesn't sound so out of the ordinary to me that he would press and press and press that. Look, I know she's hurting, but I can't take it. I gotta, like, talk to her.
Melissa Carter
Well, my thing is, I think humiliated is a little over the top. Like, I mean, there's a miscommunication between you and Phil. I don't know why you would think Phil would. Would stand you up when we've helped you this whole time, but, I mean, if things just didn't work out. They didn't work out. But I mean, I don't understand why you felt humiliated in front of Ian.
Penelope
Well, because I looked nice. I was ready for. I was, you know, we're ready for a date and somebody doesn't show up.
Adam
So you get in the car and tell him you're going to meet Phil somewhere.
Show Host
Didn't happen.
Penelope
No, that didn't happen.
Show Host
So you initially, like, right at the outset, said that you need help because things now are gone horribly wrong. So what has gone horribly wrong since then?
Veronica
Well, Phil stood her up, so she's humiliated.
Show Host
That's it.
Penelope
Uh huh.
Show Host
That's. No, that's not.
Melissa Carter
Well, my thing. I mean, I guess my thing is like if. Cause sometimes things just don't work out. Like you had plans and then. Well, they just didn't, you know, it just. Then you didn't. But.
Penelope
I know, but I was still humiliated. Waiting for a date, you know, looking nice and didn't work out.
Adam
I think that what we're missing here is that, you know, Penelope's told us from the beginning that she needed help, which means she lacks the ability to improvise. Improvising in this situation would have been, you know, pretending to be on the phone or actually checking your cell phone and calling Phil and maybe faking a conversation saying, okay, that sounds great, I know traffic's bad, I'll meet you there. And then go on your little pseudo lunch date. Which would have accomplished the same thing as actually going out with Phil is pretending like you had plans. But the improvisation factor in this dating game has been missing from the start.
Veronica
So she's not capable of it.
Adam
We're assuming she'd be able to do that.
Show Host
Well, what coulda does?
Adam
I know what assuming does.
Veronica
Playing Frisbee with a guy with no hands, huh?
Show Host
You just keep looking up. Cause that's where it all is. Penelope, I understand that it didn't work out well for you, but the panic that I hear, like, oh, things are gone so bad. I was humiliated. This, none of this, I think, plays into what his reaction would be to you.
Melissa Carter
Well, it depends on. Okay, so I want to know what happened. Okay? Phil. You figured out that you and Phil were not going to lunch. So I want to know what happened from lunch until the end of the day yesterday. Conversations you had with Ian.
Penelope
None.
Melissa Carter
None.
Veronica
Why do you sound so mad at us?
Penelope
Just because I'm feeling I'm supposed to have the guy by now.
Melissa Carter
I'm sorry, what?
Show Host
You feel like you should have gotten the guy by now.
Penelope
Oh, yeah. It's just been so long.
Melissa Carter
Well, honey, wait. Honey, we.
Veronica
And whose fault is it that you don't have the guy?
Penelope
Oh, wow.
Show Host
Well, keep that up. I think it's his.
Melissa Carter
Because the thing is, you got a date. Like, he asked you out, and we. And you went on a date. It's not our fault that he was a jerk to you on your date.
Veronica
But I think she thinks it's our fault.
Melissa Carter
Well, that's ridiculous. You got the date or Phil's fault.
Veronica
For standing her up.
Melissa Carter
And then. We're trying to help you. Like we told you, we think that he treated you unfairly and that you deserve better. But you decided that you wanted this guy so badly, so we're trying to help you get him back.
Show Host
You couldn't even approach this guy when we talked to you. Now you're setting up dates. You've gone on group dates, so you kind of. I think things are progressing just fine.
Penelope
Okay, yeah, well, maybe there's a little.
Show Host
Education going on here also. Like, maybe this is the reason why you've said that you've had no luck at all dating. Maybe you push things along too quickly. Like, you show too much eagerness right off the bat.
Melissa Carter
Mm.
Veronica
Crazy.
Adam
You do have to hold something back, I think, at the very start, just to sort of play that cat and mouse game. Guys love the chase.
Show Host
That's what we've been telling you since minute number one.
Melissa Carter
He asked you to lunch yesterday. I mean, like, he's. He's. You know. And all we've told you is to make sure that he doesn't treat you poorly again. That. That's why you needed to kind of make him work a little harder for that second date because he was so horrible to you on the first one.
Penelope
I'm ready.
Adam
For what?
Melissa Carter
Yeah, I mean, for what? Yeah.
Veronica
You can't, like, I don't know, that you have the right attitude. Yes. Attitude or spirit right now to find love. It sounds like you're harboring a big chip or something.
Show Host
She just wants to be with this dude no matter what. Our advice is not gonna matter.
Melissa Carter
Well, then she can take.
Adam
Do her own thing.
Veronica
Yeah, but why? She can't get mad at us for pushing her along.
Melissa Carter
Yeah, I mean, if you want to do your own thing.
Show Host
Veronica, good morning. You're on all the hits. Q100.
Veronica
Look, you can't get mad at me. Hey, guys.
Penelope
I love you guys. Hey, I just had one thing to say. Penelope is so gone, off the edge, she is gonna make excuses further down the road. For Ian. And he's just gonna be her, like, dating Antichrist one day. And then you can have her back on it further down the road for another bit. Just let her go. She's. She's gonna make excuses for this guy. She. It doesn't matter at this point.
Show Host
I think there's some validity in what she's saying. Like, it doesn't matter at this point what we say. You want this guy so badly that you can't see things clearly. And I don't. I don't even know that I'm comfortable even still setting you up with this dude. I don't think he's a good guy. Yeah, I'm not sure he's a great guy.
Adam
Well, I think that he could be a great guy that made a terrible dating mistake. And some mistakes in dating you just don't recover from, like, spending 90 minutes talking and arguing with your ex girlfriend while you're on a first date with another girl. Normally, just don't recover from that.
Show Host
Well, and then not apologizing the next day.
Adam
Exactly.
Show Host
Big time strikes right off the bat. Yeah, that's character stuff there.
Veronica
Like, as we told you last time, like, you probably shouldn't. Like, it should have ended when he did that.
Adam
Yeah. You know, if you were going to be a hot commodity, you would have just lost interest completely right there, Pierre.
Veronica
Kind of like you are with us.
Melissa Carter
Exactly.
Veronica
Yeah. You need to treat Ian the way you're treating us.
Show Host
Hey, Pierre. Good morning.
Penelope
Good morning. Virtual. Yeah. I think you're wasting your time with this girl. I mean, she's stupid. Sorry to say that. You wasting your time. She's made up her mind a long time ago. If this is. And she's going to be heartbroken.
Show Host
So you think it doesn't matter. What advice doesn't matter. Yeah, it doesn't matter.
Adam
Can we just keep him on the phone?
Show Host
You like that accent?
Melissa Carter
Talk some more.
Adam
Yeah, just say some other things to us.
Veronica
I say that one's fake.
Show Host
Pierre, what part of France are you from?
Penelope
No, I'm from Central Africa. From Cameroon.
Show Host
Which used to be owned by the French.
Veronica
Yes. All right.
Show Host
Thank you.
Melissa Carter
Yeah, you need to go by his accent, not his name. Bert.
Show Host
So.
Veronica
So you're from deep southern Pierre.
Adam
That was the name of half of the males in my class in French, too.
Show Host
Pierre.
Adam
Because you know how the teacher has to give you a French name?
Show Host
Everybody wanted to.
Veronica
That was my name in Spanish class, too.
Show Host
Penelope. I'm not exactly really sure where to go. He has not said to you, let's go out this weekend?
Penelope
No, but I also haven't given him every opportunity to do so.
Melissa Carter
Yeah, I. You know, my feeling now is that we accomplished what we set out to do with her. We got her the guy on the date, the date went badly. Because if he. Him. Not because of Penelope, because of Ian, then we gave the advice. Well, I mean, he doesn't look. Sound like he's a good guy. Penelope still wants to pursue him, and I say let her pursue him on her own.
Adam
Penelope, just curious. What are you blinded by with this guy? Because, obviously, you know, you're a cool girl. You've got this cool internship, you're in school, you got everything going for you. Why is this guy, like, able to be a jerk, but you still want him? What is it about him?
Penelope
I think everybody's had that guy in their life that may have messed up, but they really feel a connection with.
Adam
So you feel a connection with him, that's why you're blinded? Or is he just, like, hot? Like, what's the deal?
Penelope
It's everything. He's it for me.
Adam
He's what?
Penelope
He's it for me.
Adam
It's called dating Antichrist.
Veronica
He set your loins on fire.
Adam
Not yet. She's had one failed date with him. It's going there. He can't be the Antichrist.
Show Host
Yeah. She's on her way to dating Antichrist.
Melissa Carter
Let her do it. Like, the thing is, on her own.
Adam
Let her do it.
Melissa Carter
Yeah. On her own. Because, I mean, the thing is, Penelope, I mean, honestly, I mean, I just think that we have helped you. And. And, yeah. And I just think that just your attitude this morning is what I. I'm like. You know what? Good luck. Bye. Bye.
Penelope
All right. Thank you.
Show Host
That's it.
Penelope
Yeah. I'm gonna do it myself.
Show Host
You don't really. You don't need our advice. You don't want our advice. You want to do things by yourself.
Penelope
I'm gonna do it by myself.
Show Host
Okay. All right. I think that's it.
Penelope
Thank you.
Show Host
All right.
Veronica
Can you just put all my stuff in a box?
Show Host
I'm gonna send back. Oh, she's gone.
Adam
Oh, dang. That's the second person that's hung up on us today.
Show Host
She didn't. You know what? This was stupid.
Melissa Carter
She was mad at Phil. That was mad at she. And the humiliation in front of Ian, and it's like, that was ridiculous.
Adam
Improvise.
Melissa Carter
Yeah.
Adam
You know, that's what you gotta do.
Melissa Carter
And don't be humiliated is such a strong word. It was like, plans change, and it was lunch, and it's no big deal.
Show Host
Well, because she feels like there's so much at stake with this guy. The fact that Phil didn't show up. She really feels that is a crisis. Like she was totally humiliated in front of him. She can't see things. She does. She's not going to take our advice from here on out. She wants to be with this guy. It would have worked fine. We had it going fine.
Melissa Carter
Yeah, we. We accomplished the goal. Yeah.
Veronica
He went to. Where did he go again?
Melissa Carter
They went to Athens.
Phil
Athens.
Veronica
Where he hooked up with his ex girlfriend for 90 minutes. Arguing or making out, it doesn't matter. There's still passion.
Melissa Carter
And I still think, like I said before, like, both Ian and. Ian and Penelope are going to Athens this fall. And I do think that ex girlfriend is in Athens. And I do think Ian's eventually going to get back together with her when school starts.
Adam
It's passion. And if anybody knows passion, it's Jeff dollar passion.
Veronica
That's for sure. Sometimes I say it like this.
Adam
Passion.
Veronica
And that means a lot of passion.
Adam
Save that.
Show Host
Yeah. I mean, the way she hung up the phone, she was over this whole thing when she got on the phone with us, which is fine. I'm just sorry that we wasted so much time with her over the last couple of weeks because we had her at a place where if he was a decent guy, things would have been fine. Yeah.
Adam
I think everybody can learn from her overeager mistakes. That. And if you are waiting on somebody to come meet you for lunch and they are not there yet, why would you not at least check your voicemail?
Melissa Carter
Like, look at your cell phone?
Adam
I mean, that's nuts.
Veronica
Well, if you heard her, she was having a weird day.
Melissa Carter
It was.
Adam
Her phone was weird that day. Yeah.
Show Host
Morning, Burchell. Hello.
Penelope
Hi.
Adam
Good morning. How are you?
Show Host
Good. How are you?
Penelope
I'm doing great. You guys need to tell her to just call back, try to win the money and get some therapy.
Melissa Carter
Cute cash card for you.
Adam
Penelope.
Show Host
You are absolutely right.
Penelope
She is a beanbag. And it no help. She needs professional help.
Show Host
Yeah. This thing's done. Thank you, Melissa.
Adam
Bye.
Show Host
Bye. Now.
Phil
The first show.
T-Mobile Announcer
Introducing family freedom from T mobile. We'll pay off four phones up to 3, 200 and give you four free phones all on America's largest 5G network. Visit t mobile.com family freedom. Up to 800 per line via virtual prepaid card. Typically takes 15 days. Free phone via 24 monthly bill credits with finance agreement. Example Apple iPhone 16, 128 gigs. $829.99 eligible. Trade in example iPhone 11 Pro for well qualified credits end and balance due if you pay off early or cancel.
Melissa Carter
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Melissa Carter
Prices that get your budget at DSW stores or dsw.com.
Date: November 10, 2025
Main Cast: Bert, Melissa Carter, Veronica, Adam, Phil, Penelope (caller)
Episode Theme: The ongoing romantic drama of Penelope, an intern struggling with dating confidence, and her quest to "get the guy"—Ian—at her office. The show’s team tries to coach her through the highs, lows, and missteps of navigating office romance, jealousy tactics, and self-sabotage.
This episode revisits Penelope’s weeks-long saga on The Bert Show as she attempts to win over Ian, a colleague she’s infatuated with. The team recaps their advice and the convoluted dating maneuvers—like making Ian jealous with Phil—which ultimately unravel due to miscommunication. Emphasis is on how self-doubt, eagerness, and lack of dating improvisation contribute to dating dilemmas. Tensions rise as Penelope’s frustration mounts and the show weighs at what point to step back and let her learn on her own.
Penelope on her struggle:
"In any other realm of my life, I do fine, I'm confident, I'm social, but when it comes to dating and guys that I really like, then I lose all cool and I don't know what to do." (01:16 – Melissa Carter recounting Penelope’s words)
On dating tactics:
"Improvising in this situation would have been, you know, pretending to be on the phone or actually checking your cell phone and calling Phil and maybe faking a conversation..." (09:22 – Adam)
Penelope’s disappointment:
“I feel like I should have the guy by now.” (10:46 – Penelope)
On Penelope’s attitude:
"She just wants to be with this dude no matter what. Our advice is not gonna matter." (12:44 – Show Host)
Listener’s blunt take:
“Penelope is so gone, off the edge, she is gonna make excuses further down the road. For Ian... she's gonna make excuses for this guy.” (13:01 – Veronica, listener)
Host’s honest frustration:
"I just think that we have helped you... I'm like. You know what? Good luck." (16:32 – Melissa Carter)
The episode is lively, irreverent, and full of playful sarcasm, but layered with genuine concern and exasperation for Penelope’s emotional struggle. The show’s playful ribbing turns pointed as they realize Penelope is stuck on Ian regardless of red flags, and their tone shifts from guidance to tough love and eventual resignation.
This episode provides a microcosm of modern dating struggles: miscommunication, the temptation to use jealousy, the pitfalls of over-eagerness, and the importance of listening to trusted advice. The cast’s dynamic, the listener call-ins, and Penelope’s emotional candor create a mix of humor, hard truths, and relatable cringe, culminating in her decision to pursue Ian alone against the collective wisdom of the show. It’s a sharp, funny, and sobering take on why sometimes, you have to let people make their own mistakes in love.