The Bert Show – Vault: 2nd Date Update - Jessica & Ken

Date: October 28, 2025
Podcast Host: The Bert Show Cast
Featured Speakers: Ryan, Jessica, Ken, and listeners

Episode Overview

This episode is a classic installment from The Bert Show's beloved "2nd Date Update" series, where awkward dating situations get unravelled live on air. Today’s scenario dives into an epic misunderstanding between Jessica, who believes she went on a promising first date with Ken, and Ken, who is adamant that their meeting was strictly business—and that he’s married. The segment showcases confusion, miscommunication, and the comedic fallout when expectations collide.

Key Discussion Points & Insights

1. The Setup: Jessica Seeks Answers

Timestamp: [01:59]

• Jessica reaches out to The Bert Show curious about why Ken hasn't called her back after what she felt was a great date involving a movie and drinks.
• Ryan sets the scene for the listeners and connects both Jessica and Ken live on air:

  "We've got a bit of a question for you because Jessica's a little miffed... she can't figure out why you haven't called her back for a second date." — Ryan [02:23]

2. The Confusion: Was It a Date?

Timestamp: [02:38]

• Ken responds with surprise, categorically stating:

  "Oh, my gosh. We didn't go on a date. What? You know we didn't go on a date." — Ken [02:38]

• Ken reveals they first met at a party where his wife was present, and affirms his marital status.
• The outing in question (movie and drinks) was with Ken’s 13-year-old daughter and her friends, not a one-on-one date.

3. Differing Impressions: Flirtation & Intent

Timestamps: [03:04] – [04:44]

• Jessica maintains that Ken was friendly and offered to pick her up, interpreting this as romantic interest.
• Ken insists all his actions were related to a business connection—Jessica is a networking coach, Ken works in sales, and he sought professional advice.
• Ken:

  "She coaches people on how to network. I work in sales... My wife was standing right there with me..." — Ken [03:04]

• Jessica claims Ken was flirting with her at the party, to which Ken audibly groans.

4. The Movie Night: Mixed Signals

Timestamps: [04:18] – [05:01]

• Jessica feels picked up, paid for, and accompanied at the movie—classic date signals.
• Ken reiterates that the movie was a family event and the follow-up drinks were at a mall food court with kids present.
• When Jessica wasn’t surprised by the presence of Ken’s daughter, she rationalized:

  "I thought, you know, sometimes when you go on a date with someone, they want you to meet their kids." — Jessica [04:53]

5. Fallout: Messages and Misunderstandings

Timestamps: [05:01] – [05:49]

• Ken’s wife heard multiple voicemails from Jessica, escalating the awkwardness.
• Jessica comments that Ken was physically close during the movie; Ken attributes this to his daughter being frightened during the film.

  "My daughter was afraid of the movie. She was practically in my lap." — Ken [05:18]

6. Resolution: Realization & Embarrassment

Timestamps: [05:53] – [06:15]

• Ryan and the hosts highlight the breakdown in communication, with Jessica finally conceding,

  "I mean, obviously, we got our signals crossed." — Jessica [05:35]

• Both parties hang up, with an air of resignation and embarrassment.

7. Listener and Host Reactions

Timestamps: [06:18] – [07:14]

• Listeners and hosts weigh in, some defending Ken and others expressing second-hand embarrassment for Jessica.
• Notable listener quote:

  "She played herself with a capital P. How in the world do you think...he don’t want you? She needs some friends." — Cicely [06:34]

• Ryan reflects on the power of wishful thinking:

  "I think maybe sometimes you just see and hear things that you want to see and you want to hear." — Ryan [07:03]

Notable Quotes & Memorable Moments

• "We didn't go on a date. What? You know we didn't go on a date." — Ken [02:38]
• "My wife was at the party also." — Ken [02:51]
• "He was also sitting very close to me in the movie." — Jessica [05:11]
• "My daughter was afraid of the movie. She was practically in my lap." — Ken [05:18]
• "Can I go?" — Jessica, realizing the situation [06:11]
• "She played herself with a capital P." — Listener Cicely [06:34]
• "This woman smoked too much crack." — Ken, in post-call commentary [07:17]

Important Timestamps

• [01:59] – Segment begins, Jessica explains her confusion to the hosts
• [02:38] – Ken’s surprise and declaration that it was not a date
• [03:04] – Ken explains the business context of their interactions
• [04:18] – Disagreement about the signals and invitations
• [05:11] – Jessica discusses proximity at the movie
• [05:35] – Jessica acknowledges crossed signals
• [06:34] – Listener Cicely’s commentary on Jessica’s misreading
• [07:03] – Ryan’s reflection on human perception and misunderstanding

Tone & Style

• Authentic, lighthearted, and filled with genuine moments of cringe and empathy.
• The hosts maintain a friendly, humorous, and occasionally teasing rapport with both participants.
• Listener call-ins add a candid, unfiltered edge—ranging from supportive to brutally honest.

Conclusion

This 2nd Date Update segment is a classic case of mixed signals, where one person’s networking opportunity is another’s would-be romance. The episode captures the best of The Bert Show’s charm: humorous, real, and occasionally mortifying dating moments dissected for all to learn (and laugh) from. The responses from both the studio cast and audience reveal how varied perceptions can be—and how sometimes, you just need a radio show to set the record straight.