The Bert Show

Episode: Vault: Has This Digital Crush Gone Too Far?
Date: April 7, 2026

Episode Overview

This episode dives into a lighthearted, but thought-provoking listener dilemma: When does a digital crush cross the line into stalker territory? The hosts take a call from Beth, who, after purchasing a used cell phone, discovers over 60 un-erased photos of a handsome stranger. Captivated by the man in the photos, she’s tempted to “engineer” a real-life meet-up—and enlists the Bert Show crew to help her figure out where the line is between creating your destiny and straight-up creeping.

Key Discussion Points & Insights

1. Beth’s Dilemma: From Phone Purchase to Digital Crush

• [02:34] Beth recounts buying a used phone via a “friend of a friend of a friend.” When she turns it on, she finds around 60-70 photos of a “gorgeous guy” involved in various activities.
• She notes: “This is, like, potentially the most handsome man that I have ever seen in my whole life… I get to see this guy in all phases of his life.” (Beth Caller, 03:30)
• Beth feels she knows his hobbies, favored hangouts, and even his workplace just from these pics.
• Beth reflects: “It’s like someone just handed me this thing and said, here is information about this guy…” (03:59)

2. The “Stalker” Line and Digital Curiosity

• Hosts’ immediate reactions acknowledge the ethical gray area. “If you think you’re stalking, you probably are.” (Beth, 02:24)
• Beth wonders if showing up at his favorite bar is “stalking or just… creating my own destiny?” (Beth Caller, 05:37)
• The show debates whether acting on this information is destined romance or something less savory.

3. Is It Fate—or Creepy? The Destiny Conversation

• [06:05] Burt “wax[es] philosophical” about fate: “If she shows up where she thinks he’s going to be… and they hit it off, aren’t those signs of destiny?” (Burt, 06:18)
• The rest of the crew is more skeptical, with Beth groaning: “Oh, gosh.” (Beth, 06:09)

4. Does the Ex-Girlfriend Factor Change Things?

• [06:48] The group questions if the girl who sold the phone is the guy’s girlfriend; most agree that only someone in a relationship would have so many pictures of a guy.
• “Nobody has that many pictures of the same person on their phone unless they’re in a relationship with them.” (Friend 1, 07:23)

5. Listener Call-In: Just Ask!

• [07:44] Listener Lindsay suggests: “Don’t Sherlock Holmes this stuff anymore. Just ask the friend of a friend of a friend” (Lindsay, 07:44)—to which Beth’s not sure, as she barely knows the seller.

6. Hypotheticals, Humor, and Gender Stereotypes

• Playful banter ensues about mirror selfies and whether the guy might be gay, given the number of shirtless photos.
• “The old phone owner could be best friends with a gay guy is what I’m saying.” (Friend 1, 08:59)
• “Straight guys are not attractive, especially with their shirts on.” (Friend 2 [joking], 09:17)

7. Next Steps—Is This a Romcom or Just Weird?

• Burt summarizes the options:
  a. Trace the email chain and learn more.
  b. Try and bump into him at his favorite bar (“see if you meet him spontaneously, quote unquote”).
  c. Just leave it alone.
• “If you go, then you create the situation… I don’t think it’s stalking.” (Beth, 09:45)
• “If it does work out and Bert’s destiny does prevail, then this is a story you don’t tell him for a long time… like, 25th anniversary.” (Beth, 09:51)

Notable Quotes & Memorable Moments

• On initial discovery:

  “I mean, it’s just like, everything that I like doing, he’s like, he’s doing. …Someone basically just handed me this thing and said, here is information about this guy.”
  —Beth Caller, 03:59

• On ethical boundaries:

  "If you think you’re stalking, you probably are."
  —Beth, 02:24

• On destiny vs. engineering fate:

  “If he happens to be there when she’s there this weekend and they hit it off, isn’t that… Aren’t those signs of destiny?”
  —Burt, 06:18

• Listener advice:

  “Don’t Sherlock Holmes this stuff anymore. Just ask the friend of a friend of a friend.”
  —Lindsay, 07:44

• On plausible deniability:

  “And if Bert’s destiny does prevail, then this is a story you don’t tell him for a long time. Like, 25th anniversary.”
  —Beth, 09:51

Important Segments & Timestamps

• [02:34] — Beth explains the phone, the photos, and the birth of her digital crush
• [05:37] — Debating going to his hangout: “Is that stalking?”
• [06:05] — Burt discusses “destiny”
• [06:48] — Relationship status speculation
• [07:44] — Lindsay calls in with advice: stop the sleuthing and just ask
• [09:45] — Hosts agree: showing up isn’t necessarily stalking—just don’t reveal the backstory too soon
• [10:08] — Beth’s “homework”: to attempt a chance encounter and report back

Tone & Takeaways

The hosts keep things light, playful, and a little bit snarky, blending genuine curiosity with healthy skepticism. While everyone acknowledges the “fine line” between romance and overreach in the age of digital breadcrumbs, most ultimately lean towards “manufacturing destiny” as mostly harmless—so long as boundaries and privacy are respected.

Key Takeaway:
The internet has made it easy to gather info, but intent—and how you act on it—matters. A chance meeting is cute; lurking with insider knowledge and not owning up to it… maybe not so much. And if it results in a love story, maybe wait until the 25th anniversary to reveal all.