Vault: 2nd Date Update - Rick & Alica

Summary

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The Bert Show - Vault: 2nd Date Update - Rick & Alicia

Host: Bert & Cast (Lindsey, Melissa, Jeff)
Date: October 27, 2025

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Episode Overview

This throwback "2nd Date Update" episode dives into what went wrong after a seemingly fantastic first date between Rick (Richard) and Alicia. The episode explores communication, honesty, expectations in dating, and the unique challenges faced by single parents. Rick wants to know why Alicia hasn’t returned his calls after what he considered a perfect night out—a night that included high-end dinner and late-night fun. The truth comes out live, revealing clashing outlooks on dating when children are involved.

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Key Discussion Points & Insights

1. The Setup: Rick’s Side of the Story

• [01:44] Bert recaps Rick’s experience:
  • Rick went all out on a first date with Alicia: dinner at the Palm, a movie, and the Velvet Room.
  • He spent $400–$500 and felt they had a real connection.
  • After several calls went unanswered, Rick sought clarity on air.

"He thought it'd be a good idea to call us up yesterday and call Alicia out on the air while he was talking to her and find out exactly why there was no second date." — Bert [02:27]

2. Alicia’s Revelation

• [03:09] On air, Alicia reveals she has a three-year-old son, which she didn’t mention during the date:
  • She states she’s looking for more than a boyfriend—she wants a partner and a dad for her child.
  • Alicia felt Rick’s expressed disinterest in “settling down” made a 2nd date a dead end.

"I'm not just looking for a boyfriend or a husband. I'm also looking for a dad for my little boy. And you, you failed the audition." — Alicia [03:49]

3. The Debate: Disclosure and Responsibility

• [04:18] Rick’s reaction centers on not knowing about the child and his financial “investment” in the date.
• [04:32] Co-hosts and Alicia challenge Rick’s notion that she owes up-front disclosure and critique his attitude about expenses:
  • Lindsey: It was Rick’s choice to spend lavishly, Alicia never demanded it.
  • Melissa & Lindsey assert Rick is being unfair and rude for using the word “baggage.”

"It was your choice to spend that much money. She never said to you, I need a fancy, schmancy date." — Lindsey [04:37]
"Not to be rude, but, you know, baggage, if you can." — Rick [05:14]
"Rich, what is wrong with you? ... Now I understand why she doesn't tell anybody about the kid. Because you totally treat her differently and insult her." — Melissa [05:37]

4. Should a Single Parent Disclose Right Away?

• [06:19] The table debates if women (or men) should mention kids before or after the first date.
  • Alicia admits she rarely discloses being a parent on the first date; usually tells by the third or fourth.
  • She and the hosts discuss why: “The guy treats you differently” if they know up front.
  • Jeff voices concern: “Don’t you feel like you’re kind of roping them into it if you wait that many dates?”

"None of my friends do. No, because the guy treats you differently. Look at how Richard's impression of me has changed." — Alicia [06:28]
"Part of your package now is your son." — Jeff [07:48]

5. Reflections & Dating Realities

• [07:17] Bert and the team probe Alicia on her dating patterns:
  • She confirms she typically waits until date 3 or 4 to tell dates about her child, and reactions vary.
  • Alicia recognizes she also needs to evaluate men before letting them into her child’s life.

"I want to get to know them, too. I don't want to introduce my child to some guy who isn't what he seems to be. … A lot of guys act really nice on the first few dates because they're trying to impress you." — Alicia [07:58]

6. Where It Stands & Takeaways

• [08:36] Melissa points out Alicia chose not to continue after sensing Rick wasn't ready for her situation.
• [08:47] The hosts suggest perhaps a more direct, prompt conversation could help avoid confusion or hurt feelings in future.

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Notable Quotes & Memorable Moments

• "You, you failed the audition." — Alicia [03:49]
• "Oh, I mean, it was kind of just like a free night out for mom, otherwise." — Rick [04:32]
• "My child's not a dog." — Alicia [06:47]
• "If you were an honest person, you would have tried to impress me so hard." — Alicia [06:11]
• "We also have to remember that she decided not to go out with you again. … She cut it off when she realized that you weren't gonna be interested in that." — Melissa [08:36]
• "Maybe that's where the real fault lies there, Alicia. ... you called him up and then said, you know what? I just realized you're not the kind of guy that I'd want to go out with because I have a child. Maybe that's the way to handle it." — Bert [08:47]

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Timestamps for Important Segments

• [01:44] — Bert introduces the segment, recaps Rick’s story
• [02:27] — Alicia joins the call and the truth starts to unfold
• [03:49] — Alicia reveals she has a child and her reasons for not disclosing
• [04:18] — Rick laments about spending money, says he wouldn't have gone had he known
• [04:37] — Lindsey and other hosts challenge Rick's fairness and “baggage” comment
• [06:19] — Hosts and Alicia debate when to reveal she’s a parent
• [07:58] — Alicia explains wanting to vet dates before letting them into her child's life
• [08:36] — Melissa reiterates Alicia made the choice to end things

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Tone & Takeaways

The tone is candid, playful, and sometimes intense—true to The Bert Show’s real-talk style. The cast doesn’t shy away from calling out awkwardness and sparking honest discussion. The episode sheds light on dating as a single parent, the fine line between transparency and vulnerability, and the pitfalls of expectation versus reality.

Best for: Anyone navigating dating with kids, or curious about modern relationships and hard truths.

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Transcript

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[Bird]

The Bird show for the life of me, I can't figure out why guys want to do this every week. But here's second date update. Here's the premise behind it. Guy goes out with woman, thinks he has a great date. Can't get return phone call back. So what he'll do is what I think is really the smart way to go. Call her live on the air and find out why she won't return his calls. All right, let's go ahead and reset this. Richard Rick calls us up yesterday, has a great, great first date with Alicia, takes her to the Palm.

[Lindsey]

Yes.

[Bird]

Takes her to Blue Palm. Oh, yeah, takes her to a movie, takes her to the Velvet Room. They hang out till three in the morning, has a great time. So he's expecting a second date. He calls her back once, twice, three times, no callback.

[Lindsey]

Drops about $400.

[Bird]

Yeah, $400 or $500 on her and can't figure out why. So he thought it'd be a good idea to call us up yesterday and call Alicia out on the air while he was talking to her and find out exactly why there was no second date. So we did that. We called Alicia on the air. Hi, Alicia. Hello. Hi, this is Bird and Lindsey and Melissa and Jeff calling from Q100. Hey, Alicia, we have Richard on the phone here with you and he thinks that you guys had a great first date. Couple of weeks ago, he said that you guys had a great first time time at the Velvet Room. Dinner was great, the movie was kick ass. And he's called you a couple of times, emailed you a couple of times. And he's just been getting the cold shoulder and. Well, Richard, why don't you talk to her?

[Richard (Rich)]

Hi, Alicia.

[Alicia]

Hi, Rich.

[Richard (Rich)]

Yeah, what, what's going on? How come I haven't heard from you?

[Alicia]

Well, I had a great time with you and I thought so. Well, to be honest with you, during the course of the evening you made this statement about how you really worked hard in your 20s and now that you've turned 30, you want to start playing a little more. And I didn't tell you, but I actually have a three year old son.

[Richard (Rich)]

You have a three year old son?

[Alicia]

Yeah. And I know you're not looking to get married yet and you want to just kind of play and have fun for the next few years and you're not looking to settle down.

[Richard (Rich)]

You're not kidding. You have a three year old son?

[Alicia]

Yeah, I have a little boy. And I don't tell people when I go on a date with a guy. Just getting to know him, it's kind of like an audition, you know, because I'm not just looking for a boyfriend or a husband. I'm also looking for a dad for my little boy. And you, you failed the audition.

[Bird]

That's legit. I mean, she just feels like, yeah, she just feels like she's looking for somebody a little bit more settled, you know, some. She's also looking for, I mean, inevitably a father and somebody that she can spend the rest of her life with.

[Richard (Rich)]

I understand it. She has a kid that she's got to look out for. Not only herself, but the child is. I wish I had found out earlier, because, to be honest, I probably wouldn't have wasted all that money.

[Bird]

Oh.

[Richard (Rich)]

I mean, it was kind of just like a free night out for mom, otherwise.

[Bird]

Aw, that's okay, Rich, you know.

[Lindsey]

Okay, you know what? That's not nice. That's not fair. And also, it was your choice to spend that much money. She never said to you, I need a fancy, schmancy date. You could have taken her out to a nice restaurant and that's it. And that would have been a fun evening. She wasn't asking to. For you to drop $400 for her.

[Bird]

Alicia, you want to respond to him for all the single moms listening?

[Alicia]

Well, yeah. I'm kind of taken aback that he would say something like that. It isn't as if I asked you to take me to the Velvet Room into the Palm. I would have been just as happy if we'd done something less expensive. And it's not as if you asked if I had any kids.

[Richard (Rich)]

Well, I understand, but it's not as if you said either. I just think it. I don't see anything wrong with me taking you out, doing the best I can, the date, and treating you as well as I can. Obviously, I did it not knowing at all that you had, you know, not to be rude, but, you know, baggage, if you can.

[Melissa]

Rich, what is wrong with you? I mean, see, a little.

[Richard (Rich)]

I understand that she.

[Melissa]

You would not have taken her out if she had. Now understand why she doesn't tell anybody about the kid. Because you totally treat her differently and insult her.

[Bird]

What do you mean by her child? It's not baggage.

[Richard (Rich)]

Well, just be honest is all I'm saying up front from now on.

[Jeff]

Why does every guy who comes on this stupid second date thing bury themselves in singlehood forever?

[Bird]

Cause it's ego.

[Richard (Rich)]

It's not ego.

[Bird]

Yeah, it is.

[Richard (Rich)]

No, it's not. They.

[Bird]

Alicia.

[Richard (Rich)]

Alicia, didn't you expect me to be completely honest with you? I just expected the same.

[Alicia]

Well, if you were an honest person, you would have tried to impress me so hard.

[Lindsey]

Exactly.

[Richard (Rich)]

Well, I don't think that that's fair, is there?

[Bird]

Hey, Alicia, is there some validity to telling people before you go out on a date that you have a child? Is that something that other single mothers tend to do?

[Alicia]

None of my friends do. No, because the guy treats you differently. Look at how Richard's impression of me has changed.

[Bird]

Right, right.

[Alicia]

Just finding out that I have a little boy now. It's completely different.

[Richard (Rich)]

No, well, it's not like, hey, I didn't know you were allergic to dogs. And I have a dog at my apartment.

[Alicia]

My child's not a dog.

[Richard (Rich)]

I know, exactly. It's a big, big deal that you really should let people know ahead of time. But what if some guy had taken you out and you're having a great time and everything, and later on you find out that maybe he's been divorced a couple times and has, like, five kids and one at home and a few others with a couple other women or something? Aren't these things that you'd want to know up front what you're getting into?

[Jeff]

But I think up front is fair enough to be after the first date.

[Lindsey]

Exactly.

[Alicia]

Yes.

[Melissa]

Yeah. I mean, do you have to put everything on the table on the first date?

[Bird]

Alicia, this isn't the first date you've had in three years, Obviously.

[Alicia]

No, it's not.

[Bird]

And you never tell the guy on the first date that you have a child. Never have before.

[Lindsey]

When do you usually tell them?

[Alicia]

Yeah, like third or fourth. Yeah, third or fourth date.

[Lindsey]

What is the usual response or the typical response?

[Alicia]

The typical response is that they're not exactly excited. Well, actually, a few guys are. You know, they're happy to get to know my son, but, you know, it makes them jumpy.

[Bird]

Sure. I think.

[Jeff]

Don't you feel like you're kind of roping them into it if you wait that many dates where you're creating an interest in yourself? I mean, part of your package now is your son.

[Alicia]

And it's not just rubbing them in, though. I want to get to know them, too. I don't want to introduce my child to some guy who isn't what he seems to be. I mean, a lot of guys act really nice on the first few dates because they're trying to impress you, but that's not.

[Richard (Rich)]

I mean, you seem to be someone who's not a single mom, and then you turn out to be a single.

[Alicia]

What's a single mom supposed to be?

[Richard (Rich)]

Well, in other words, you say nothing about a child, and then three to four days. I mean, I was lucky enough to find out after one date. You're saying you tell some guys after three or four dates? That's not fair.

[Lindsey]

See, I think I'd just be surprised after the third date or the fourth date.

[Melissa]

We also have to remember that she decided not to go out with you again.

[Bird]

Yeah, that's right.

[Melissa]

She. She cut it off when she realized that you weren't gonna be interested in that. She went ahead and just said, you know what? No more.

[Bird]

Yeah. Maybe that's where the real fault lies there, Alicia. And you just after he called you two or three times, you called him up and then said, you know what? I just realized you're not the kind of guy that I'd want to go out with because I have a child. Maybe that's the way to handle it. The bird show dude, did you order.

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[Richard (Rich)]

I never looked so good.

[Bird]

You look the same.

[Richard (Rich)]

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[Bird]

You haven't changed your hair in 15 years.

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