Episode Overview

Title: Should I Charge My Ex for His Concert Ticket?
Podcast: The Nightly – Hosted by Kristen and Jacquees
Guest: Listener Maddie (Los Angeles, CA)
Original Air Date: December 24, 2025
Theme:
A cozy late-night advice session featuring a real-life dilemma: Should Maddie ask her ex to pay her back for a concert ticket she purchased before their breakup? The episode explores themes of closure, pettiness, self-care, and reclaiming joy after a breakup—all with the show's trademark gentle humor and bedtime vibes.

Key Discussion Points & Insights

1. Setting the Scene (00:28 – 02:11)

• Kristen and Jacquees welcome listeners into the “pillow fort,” setting the show’s chill, intimate tone.
• Lighthearted banter about radio voices and confidence segues into the night’s main event: opening up the “Nightly Hotline.”

2. Maddie’s Dilemma: The Concert Ticket Conundrum (03:05 – 04:22)

• Maddie explains: She bought herself a ticket to Billy Martin’s concert, but her then-boyfriend (now ex) expressed disappointment for being left out—so she bought a second ticket for him.
• Now broken up, Maddie wonders: Should she charge her ex for his ticket, or just eat the cost?
• “Do you eat the cost, or do you reach out and charge them?” – Maddie (03:19)

3. Relationship Backstory & Motivation (04:22 – 05:54)

• Kristen digs for context: The relationship was “crash and burn,” only 3 months but intense.
• The breakup revealed “differences in opinion about the world,” and Maddie feels she never really knew her ex.
• Maddie isn’t sure if her ex still expects to go, but she herself doesn’t want to.

4. Is It Petty? Or Just Fair? (05:45 – 06:15)

• Both hosts reassure Maddie:
  • Jacquees: “I love a petty queen… I love a petty king, baby. I love it. I love it.” (05:45)
  • Kristen clarifies: “I don’t think you sound petty at all.” (05:54)

5. Advice & Personal Anecdotes (06:15 – 10:31)

• Ticket use tactics:
  • Jacquees suggests it’s a “two-click Venmo request,” but cautions against expecting repayment.
  • Inspires Maddie with a personal story: Used extra Beyonce tickets after a breakup to impress someone new.
  • Advice: “Use this concert ticket to your advantage in any way that you see fit. And also, forget this person. Yeah, forget them.” – Jacquees (07:55)
• Potential to bring a new crush versus “charging” the ex for a ticket the crush will use.
• Kristen presses Maddie to consider her motivations: “Are you really over your ex, or is this just a way to stay tethered?” (08:34)
  • Kristen’s “burn it down” breakup philosophy: “If we break up, I never want to see you again or hear about you again for the rest of my life.” (09:18)
• Both land on similar advice:
  • Send the Venmo request for closure—not out of pettiness.
  • No expectations; focus on psychological release and moving forward.

6. Processing Closure & Self-Care (10:31 – 13:18)

• Maddie reflects: It’s less about money, more about “the principle behind it… just the piece that’s in it.”
  • “I think that I do need to do it. And whether or not he fulfills it, up to him. But like, that’s out of my court.” – Maddie (11:03)
• Jacquees: “There’s nothing wrong with doing things for yourself… We are all about comfort… feeling true to what you’re feeling.” (11:15)
• Maddie highlights she initially bought the ticket to treat herself, not her ex.
  • “I had a date by myself, and like, you made me feel bad about it. And so I bought you a ticket. And, like, now you’re not even here.” – Maddie (12:44)
• Kristen: “No matter what you do, it’s gonna be fine… Maddie, you’re taking care of yourself, and that’s all that counts.” (13:18)

7. Game Segment: “Would You Rather: Concert Edition” (15:31 – 18:49)

• The trio plays a themed “Would You Rather.”
• Dilemma: Front row with bad smells (Axe body spray) or back row with bad sound but good vibes?
  • All would brave the smell for great music.
• Kristen’s tip: Bring Tiger Balm for smelly environments, but not allowed in the scenario!
  • Laughter shared: “I might even, as I’m singing a song, be like love on top. Ooh, y’all stink around me.” – Jacquees (17:42)

8. Wrapping Up: Empowerment & Validation (18:49 – 19:51)

• Hosts express gratitude for Maddie’s vulnerability.
• Affirmation: Asking for what you’re owed isn’t petty; it’s self-respect.
  • “Like, asking for your own money back is not petty.” – Kristen (15:07)
• Invitation for other listeners to send questions.

Notable Quotes & Moments

• On Ego & Advice:
  “The ego comes in when you think people have to take your advice.” – Jacquees (01:42)
• On Setting Boundaries Post-Breakup:
  "If we break up, I never want to see you again or hear about you again for the rest of my life." – Kristen (09:18)
• On Finding Closure:
  “Say what you need to say. And it may just be the two clicks of a Venmo request. Get it out there for yourself psychologically. Then make peace with it. Don’t expect anything back.” – Kristen (09:54)
• On Taking Care of Yourself:
  “We are all about comfort. We are all about feeling relaxed and feeling good, but also, you know, feeling true to what you’re feeling at the moment, because that’s the only way you can, like, get to the other side when you wake up, you know?” – Jacquees (11:15)
• On the “Would You Rather” game:
  “I might even, as I’m singing a song, be like love on top. Ooh, y’all stink around me. I might even say something.” – Jacquees (17:42)

Segment Timestamps

• [00:28] – Show Start & Radio Voice Banter
• [03:05] – Nightly Hotline: Maddie’s Question
• [04:22] – Relationship Context & Ticket Dilemma
• [06:15] – Should Maddie Charge Her Ex? Hosts’ Takes
• [08:34] – Motivations, Closure, and Burn-it-down Philosophy
• [11:15] – On Doing What Feels Good for You
• [13:18] – Taking Care of Yourself Post-Breakup
• [15:31] – “Would You Rather” Concert Game
• [18:49] – Validation, Empowerment, and Goodbyes

Summary Takeaway

By the end of the episode, Maddie—and listeners—are reassured that advocating for oneself after a breakup isn’t pettiness but self-care. Whether Maddie requests repayment or lets it go, she’s encouraged to act out of self-respect and closure. The gentle, funny atmosphere and relatable banter create a late-night space where all kinds of post-breakup feelings are acknowledged and validated.

Listeners are reminded:
Do what feels best for your peace of mind, and never be afraid to choose yourself—especially in the pillow fort!