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

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

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.

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.

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]

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

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.