The Bert Show – Vault: Sally's Break Up

Date: November 3, 2025
Host & Cast: Bert, Kristin, Abby, Cassie, Tommy, and full Bert Show team
Episode Theme: Navigating post-breakup heartbreak with honesty, humor, and advice

Episode Overview

This episode revisits listener Sally’s breakup saga—a real-time, emotionally raw account of the aftermath of her three-year relationship ending. The show features Sally’s calls both before and after her breakup, her honest reflections, and unfiltered guidance from the hosts. Listeners get a candid “inside-out” look at processing heartbreak, the urge for closure, and the rocky road of moving forward. With compassion, tough love, and signature humor, the cast coaches Sally (and listeners by proxy) through the stages of letting go.

Key Discussion Points & Insights

Sally’s Story Recap

• Background: Sally, 23, called the previous Friday, suspecting her boyfriend of nearly three years would break up with her. He’d expressed doubts: "he's not sure if he loves me like a best friend or if he loves me like a future wife." (01:50)
• Breakup Night: He arrived early, brought dinner, and after eating, confessed uncertainty about their future. Sally confronted him, insisting, “You are not calling the shots anymore. Sit down.” (03:03)
• Aftermath: Sally ensured closure by “bombarding him with questions for about 45 minutes” and completed the painful ritual of returning each other’s belongings. She directly asked if another woman was involved—he denied it.

The Urge for Contact & Struggling with Closure

• Despite declaring herself “okay,” Sally admitted reaching out: "Actually, all of y'all are wrong. I actually ended up calling him." (04:24)
• She rationalized calling to retrieve belongings and "just say, you know what? I'm okay," after a night out with friends. (04:47)
• Over the week, contact was more frequent than she wanted to admit: “We probably talked Monday, Tuesday and today already.” (05:21)

Hosts Offer Tough Love and Guidance

• The team debates her progress and backslides, drawing analogies about breakups:
  • “Like when you get your arm cut off, you still think it’s there for a while.” (03:34)
  • “It's like you quit smoking, but you're taking drags on cigarettes every day going, you know, but I quit.” (08:24)
• They emphasize the need for space, warning, “At this point, he cannot be your best friend. You know that, right?” (07:04)
• Bert reads out the “seven stages of a breakup,” prompting Sally to identify her own progress (see below).

The Stages of a Breakup – Bert’s Readout & Group Discussion

1. Denial (10:25): "First stage involves you not accepting the current situation."
   • Sally claims she’s moved past this: "I think I'm in acceptance." (10:37)
2. Out of Control (11:50): “You make a fool out of yourself by embarrassing yourself.” Sally recounts a 7 a.m. visit to her ex’s apartment, realizing in hindsight it was cringeworthy.
3. Loneliness & Depression (13:13): "It’s the first time that it really starts to sink in...all the sappy love songs make a lot of sense to you."
   • Sally leans on friends bringing ice cream and cheesecake.
4. Blame Phase (14:11): "You analyze every part...what you could have done differently."
   • Sally tries not to blame, appreciating his honesty.
5. Anger (15:04): “You're no longer blaming yourself... you overblow all their bad traits.”
6. Acceptance (15:36): “Coming to peace with the situation, accepting the finality.”
7. Healing & Moving On (15:49): Rebuilding and truly letting go

Advice on Managing the Breakup

• The cast insists Sally minimize contact: "No communication by calling... No text messaging, no email, no leaving a note." (19:44)
• They urge symbolic gestures to help her move on: “You need to ceremoniously delete him from your cell phone.” (19:10)
• Sally’s resistance is evident: “Well, I have his number memorized.” (19:14)
• Cassie offers to be Sally’s “breakup sponsor,” encouraging her to call a friend (or a host) instead of her ex during moments of weakness. (18:23, 18:52)
• The group doubts she’ll stay no-contact over the weekend, adding accountability and humor: “She's gonna call him. Alcohol.” (21:54)

Life Context and Emotional Complexity

• Sally reveals her grandfather’s sudden illness and the recent death of a friend, noting that these heavier events have “put things in perspective.” (09:27)
• The team reflects that sometimes, bad timing or non-dramatic breakups make closure unpredictable: “This is almost what makes it worse, is that you’ll want to keep coming back and keep coming back because it didn’t end, like, badly for you.” (16:15)

Notable Quotes & Memorable Moments

• Sally asserts her agency:
  • “You are not calling the shots anymore. Sit down.” – Sally (03:03)
• Hosts compare breakups to losing a limb:
  • "Like when you get your arm cut off, you still think it’s there for a while." – Bert (03:34)
• About post-breakup relapse:
  • "It's like you quit smoking, but you're taking drags on cigarettes every day going, you know, but I quit." – Cassie (08:24)
• Sally’s raw honesty:
  • “Well, I kind of didn't. I guess I was still in shock... drove over to his apartment... at 7am and just called him when I was outside his door and I said, come let me in. I mean, it was very embarrassing now, but I guess at the time I thought, this can't possibly be happening." – Sally (12:08)
• Hosts on moving on from an ex and their family:
  • "You’re not friends with this family anymore. Like, when you break up, like, the whole thing goes." – Bert (17:12)
• On the need for space:
  • “You have to go through the pain. You just have to. Or all you’re doing is putting off the pain, prolonging it.” – Cassie (08:37)
• Sally’s bravado (with protestation):
  • “I can go all weekend and not call. That's not a problem.” – Sally (20:41)
  • Hosts in unison: “Absolutely not!” (21:13)
• Bert, wryly:
  • “She’s gonna call him. Alcohol.” (21:50)

Timestamps for Key Segments

• Sally’s original call & final breakup recount: 01:22 – 03:28
• Sally’s confession of repeated contact: 04:24 – 05:32
• The stages of a breakup explained: 10:25 – 15:49
• Advice on “no contact”, the importance of space, and the challenge of deleting his number: 18:11 – 19:35
• Hosts set Sally’s accountability challenge for the weekend: 19:44 – 20:47
• Hosts predict Sally’s “no-contact” resilience: 21:11 – end

Final Thoughts & Tone

True to The Bert Show’s style, the conversation mixes empathy, hilarity, and brutal honesty. Sally is simultaneously supported and challenged, with the hosts acting as spirited friends (and occasional “sponsors”) to keep her on the right path. The messiness of heartbreak is embraced rather than sanitized; Sally’s candor about struggling, making mistakes, and wrestling with recurring feelings makes the “therapy session” universal and relatable—reminding listeners, as always, they’re not alone.