The Bert Show

Episode: Vault: She Desperately Needs Some Tough Love - Part One

Date: November 25, 2025
Host: Bert and The Bert Show Cast (Jeff, Chad, etc.)
Caller: Wendy

Episode Overview

This episode is a classic “Tough Love” segment on The Bert Show, focusing on giving blunt, straightforward advice to listeners facing relationship dilemmas. The spotlight is on Wendy, a caller who's anxious about perceived “red flags” in her nearly two-year relationship. Instead of getting advice from her girlfriends, Wendy turns to the guys on the show—believing she'll get no-nonsense, unfiltered feedback.

Key Discussion Points & Insights

1. Premise: Guys-Only Tough Love

• Jeff introduces the segment:

  “Sometimes women can't really give the bare bones stripped down hardcore advice... those Ann feelings get in the way... Guys are going to cut right through that. If he's cheating on you, we're gonna call it. If he's a crappy guy, we're gonna call it.”
  (01:43)

• Bert says:

  "...since we write [the playbook] every single day, we can tell you guys what's really going on in your relationship if you give us all the facts."
  (02:39)

2. Wendy’s Concerns & Red Flags

• Wendy explains she's been with her boyfriend for about a year and a half and, despite his overall goodness, some behaviors are bothering her:
  • Deletes all text messages constantly:

    “He text messages all the time, and then he deletes them... I have noticed that he does delete every message he ever gets...”
    (04:21)

  • Regular late night outings with his ‘guy friends’:

    “He has a regular Tuesday night... play cards, have fun... sometimes it can be to like, midnight, 1:00 in the morning...”
    (05:32)

  • Brings clothes to work after sleepovers at a friend’s house
    • This seems practical because the friend’s house is closer to work, but it stands out as odd to Wendy (06:32).
  • “Cousins” in South Georgia he’s suddenly visiting

    “His supposed cousins... I've never met... never even heard of him talking about. But now he has, like, you know, these cousins who live in South Georgia...”
    (07:39)

  • Wendy is not invited to family trip
    • When she offers to join, her boyfriend declines, saying she’ll see them at Christmas (08:53).

3. Show Hosts React

• Hoss (guest):

  “Yeah. He's cheating on you.”
  (09:08)

• Jeff (providing nuance):

  “Adult guys don't have sleepovers.”
  (07:15) “That's not premeditated, right?... that's not, like, on a Tuesday night when you gotta work the next day.”
  (10:01)

• Bert and others clarify
  • Occasionally, guys do crash at a friend’s after a late night, but planning for it every week raises eyebrows (10:31).

4. Further Analysis: The Devil’s Advocate Angle

• Chad brings up past family surprises:

  “We did not know that Jeff had brothers, stepbrothers, until like three years into the relationship.”
  (10:41)

  • Points out men aren’t always open about family until necessary.

• Jeff (on what’s suspicious):

  “If we were dating, and all of a sudden I said, ‘Oh yeah, I'm going up to North Carolina to visit my half brother,’ you should be pretty damn suspicious.”
  (11:15)

5. Listener Callers Weigh In

• Tony asks about communication:

  “Is this one of the situations where she can call anytime she wants and hears music in the background, the guy’s laughing, playing pool... Or is this ‘don't call me Tuesday nights’?”
  (11:45)

• Wendy clarifies:

  • She can reach him, sometimes friends answer as well. She knows some of the guy friends.

• Bert:

  “Guys protect each other pretty well, so I wouldn’t count on [the friends telling you].”
  (12:46)

  • “If you call up and he's out with the guys, then you can take some comfort in that fact.”
    (12:54)

6. The Text Message Thing

• Jeff and Chad discuss whether deleting texts is normal:

  “Text message memory in your phone is not unlimited. So I delete all the incoming and outgoing text messages every so often...”
  (14:25)

  • But not as they come in (Chad, 14:40).

7. Reevaluating with More Info

• Wendy explains the friend’s place is much closer to work than her house is, which could make sleeping there logical.

  “It could take, like, probably a little over an hour... at his friend... it’s more like 10 minutes.”
  (15:07)

• Panel reverses a bit:
  • “Now that she said that, you should have told us that in the beginning... I wouldn’t have felt so dumb...”
    (15:53)

8. Final Advice & Takeaways

• Panel concludes:
  • Benefit of the doubt is warranted. He hasn’t actually been caught in a lie, and circumstances might have practical explanations.
  • Bert:

    “I think you’re okay at this point.”
    (16:01)

• Jeff (tongue-in-cheek):

  “Just keep looking, though. You’ll find some reason to keep digging...”
  (16:13)

• Chad (joking):

  “What if she just followed him this weekend a couple car lengths behind...”
  (16:33)

• Wendy, relieved:

  “That would be great. Thank you.”
  (16:22)

• Playful dig at reassurance:
  • Bert jokes Wendy was just listening for what she wanted to hear

    “I love how she says, ‘Hey, you guys did great. Thanks so much.’ Which means, hey, you guys said exactly what I wanted to hear.”
    (16:45)

Notable Quotes & Memorable Moments

• Jeff:

  “Guys are going to cut right through that. No ray of sunshine on a cloudy day.” (01:49)

• Hoss:

  “Yeah, he’s cheating on you.” (09:08)
  (later retracted after added context)

• Jeff:

  “Adult guys don’t have sleepovers.” (07:15)

• Jeff (sarcastic suggestion):

  “Start checking his email. If you could somehow get one of those spy bot things... that would help your relationship...” (16:23)

• Chad (tongue-in-cheek):

  "Just follow him this weekend..." (16:33)

• Wendy (relieved):

  "That would be great. Thank you." (16:22)

Timestamps for Key Segments

• 01:33 – Segment Introduction: Guys-only tough love advice explained
• 03:16 – Wendy presents her situation
• 04:21 – Red flag #1: Text message deletion
• 05:32 – Red flag #2: Guy’s night out and overnight stays
• 07:39 – Red flag #3: Unknown cousins in South Georgia
• 09:08 – Hoss’s blunt initial verdict: “He’s cheating”
• 10:31 – In-depth debate on adult male “sleepovers”
• 12:16 – Wendy explains she can reach him on the phone during guys' night
• 14:25 – The deleted texts: Possible reasons and counterpoints
• 15:07 – The commute factor: key reevaluation
• 16:01 – Final advice & reassurance
• 16:45 – Meta-commentary on looking for validation

Episode Tone & Style

The Bert Show crew maintains their famously candid, humorous, and slightly irreverent atmosphere throughout. They blend real empathy with teasing and comical exaggeration, keeping things light even while addressing sensitive insecurities. The “guys only” format results in a fast-paced, no-nonsense feel, but ultimately the advice is practical, not mean-spirited.

Summary Conclusion

Wendy’s concerns about her boyfriend trigger a spirited “tough love” analysis from The Bert Show’s male panel. Though initial reactions are suspicious (“He’s cheating on you”), as more context is revealed (commute, frequent phone access, mutual friends), the panel softens, generally encouraging Wendy to trust her boyfriend unless real evidence emerges. The segment highlights common dating anxieties, the importance of context, and the tricky balance between trust and vigilance—served up with the humor, authenticity, and camaraderie that The Bert Show is known for.