The Bert Show – Vault: She Thinks Online Dating Is Pathetic…So Why Does She Keep Doing It?

Episode Date: March 19, 2026

Episode Overview

This episode delves into the skepticism and resistance towards online dating through the eyes of Shawn, The Bert Show’s phone screener. Despite strongly believing that online dating is for "desperate people" and swearing it off, Shawn is challenged by the hosts to give it a fair shot. The panel breaks down her latest experiences with various online dates, explores her biases, and humorously unpacks the stigma that still lingers around meeting people on the internet.

Key Discussion Points & Insights

1. Shawn’s Initial Stance on Online Dating

• Shawn has been adamant for weeks that online dating is "stupid" and "for desperate people," despite never trying it herself.
• The Bert Show team challenges her: “You’re making a judgment about online dating, but you’ve never actually gone on a date after meeting someone online.” – Host (00:20)

2. First Online Date Recap – A Flop

• Shawn shares her attempt at an online date a few weeks prior, which she dubs as a failure.
  • “It was boring, it was dull. And I was talking the whole time. He just sat there, was very nervous.” – Shawn (00:36)
• The hosts point out she didn't maximize the online platform's matching potential, instead picking someone at random. This prompts some group ribbing about judging by photos alone:
  • “He looks fun in his pictures. You gotta tell by pictures.” – Shawn (00:57)
  • “I guess everybody can look fun in a picture.” – Bert Show Host (01:00)

3. Redo: Shawn Follows the Rules

• For her next attempt, Shawn goes "by the book," completing her online profile and focusing on compatibility.
  • “Go online, fill out the questionnaire. Find somebody that you have something in common with. 70%, 80%, 90% commonality.” – Host (01:19)
• She connects with a guy who shares her music interests and works at a college bookstore. Their first date is at the Plaza Theater, watching "The Blues Brothers."
  • “We had a lot of the same interest in music... It was a different sort of approach.” – Shawn (01:34, 03:17)

4. The Date Experience – Pros and Cons

• The group debates the value of a movie date as a first meeting:
  • “Isn't that kind of a cop out?... Movie dates in general as a first date is a bad idea. Sounds very eighth grade to me.” – Host (03:25, 03:33)
  • “It's kind of creative... When you're total strangers, it's nice to have that buffer." – Co-host (03:42)
  • Shawn appreciates the creative angle, though she notes limited conversation time.
  • She finds the guy more attractive in pictures than in real life:
    • “His hair just had this thing going on... He was average looking.” – Shawn (04:16)
• She senses more of a friendship vibe but isn’t ruling out another date.

5. Reluctance and Stigma

• Despite a better experience, Shawn’s skepticism lingers:
  • “It might be more of a friend... I could see myself hanging out with him a lot and just being friends.” – Shawn (04:34)
  • “Has it changed your mind at all about online dating?” – Host (05:10)
  • “No. And I think that may be what is still...keeping me far away because I still think it's desperate.” – Shawn (05:14)
• The hosts prod Shawn about whether social stigma is coloring her perspective:
  • “You're thinking the story that you might have to tell eventually, that you guys met on an online date, is keeping you from actually hanging out with the guy more.” – Host (05:21)

6. Group Dynamics & Running Gags

• The team suspects Shawn is holding something back, especially as she debates seeing the guy again. Their banter playfully accuses her of not being honest about her feelings:
  • “It does feel like you’re holding back, honestly.” – Host (06:08)
  • “Something’s up... it is like pulling teeth to get any info out of you.” – Host (06:22)
• Shawn insists nothing more happened, maintaining her lighthearted "always right" persona:
  • “I’m always right. I will never be wrong. It's desperate.” – Shawn (07:01)

Notable Quotes & Memorable Moments

• On picking matches:
  “You just picked a guy randomly instead of doing what you should do when you go online... you have something in common." – Host (00:43)
• On online chemistry:
  “I could see myself hanging out with him a lot and just being friends.” – Shawn (04:34)
• On online dating stigma:
  “Your soulmate... you’re supposed to find them. Not online, not narrow searches down.” – Shawn (05:28)
• Quick-fire lighthearted moment:
  “Did you spend the night at his house?” – Host (06:19)
  “No.” – Shawn (06:21)
  “Something’s up.” – Host (06:21)

Timeline of Key Segments

| Timestamp | Segment & Highlights | |-----------|----------------------------------------------------------------------------------------------------------| | 00:00 | Introduction and Shawn’s online dating skepticism | | 00:20 | Discussion about challenging Shawn's preconceived notions | | 00:36 | Shawn’s first unsuccessful online date | | 01:19 | Hosts propose "doing it right" with online dating (proper profiles & compatibility) | | 01:34 | Shawn describes her second date, choosing based on common interests | | 03:17 | Movie theater date discussed – hosts debate pros/cons of first date movie outings | | 04:16 | Shawn’s reaction to date’s real-life appearance | | 04:34 | Chemistry (or lack thereof) and openness to further dates | | 05:10 | Hosts probe if experience changed her perception of online dating | | 05:28 | Shawn admits stigma of "meeting online" influences her feelings | | 06:08 | Team questions whether she’s holding back details | | 06:22 | Banter about possible overnight stays; Shawn vehemently denies anything more happened | | 07:01 | Episode conclusion with Shawn doubling down on her "always right" mindset regarding online dating |

Tone & Style

As per The Bert Show’s trademark style, the conversation blends friendly teasing, candid listener insights, and sharp wit. The group’s chemistry keeps the banter playful yet real, striking an engaging balance between skepticism and open-minded exploration of relationships in the digital age.

In summary:
This episode humorously chronicles Shawn’s reluctance and evolving views on online dating, driven by the hosts’ good-natured peer pressure. It offers an honest look at the fears and judgments that persist, even as positive experiences begin to chip away at old prejudices—reminding listeners that even the most resistant skeptics might just end up finding something real online.