Podcast Summary: The Jordan Harbinger Show

Episode 1266: Cutting off Creep Whose Manipulation Runs Deep | Feedback Friday
Release Date: January 2, 2026
Host: Jordan Harbinger
Co-host/Producer: Gabriel Mizrahi

Episode Overview

On this Feedback Friday, Jordan and Gabriel answer listeners’ questions about complex, often emotionally fraught situations involving manipulation, boundaries, workplace injustice, family responsibility, and mental health. The main theme is navigating personal and professional relationships where manipulation, creepiness, or boundary-pushing behavior runs deep—whether it's the friend who can't take “no,” the employer exploiting staff, or a parent whose inability to accept reality puts their adult kids in a bind. The episode balances actionable advice, empathy, tough love, and humor as Jordan and Gabriel help listeners untangle their dilemmas.

Key Discussion Points & Insights

1. Recap & Recent Feedback From Listeners

• (01:13 – 04:23)
  • Jordan describes the show’s mission: decoding expert wisdom and applying it to life.
  • This week’s guest: Joe Loya, ex-bank robber who found redemption.
  • Jordan and Gabriel reflect on controversial listener feedback, particularly about a prior discussion of nicotine pouches ("Zyn") and Palestine/Israel. They note how defensive reactions to addiction topics can signal personal struggle.
    • "When you're struggling so hard with something, you feel the need to defend it like that. It's pretty intense." – Jordan (03:36)

2. Listener Question #1: Cutting Off a Manipulative, Creepy Friend

Letter Excerpt:

• Listener describes her “friend” Saul, who transitioned from being a close professional acquaintance to making inappropriate sexual comments and giving mixed romantic signals. At parties, he made crude remarks and later used her for manipulative games with his ex. She details her emotional struggle, complicated history (PTSD from past assault), and confusion about closure, especially after a failed attempt to get Saul’s brother involved for perspective.

Key Insights & Advice:

• Saul’s Behavior:
  • Saul is not only inappropriately flirtatious, but escalates into active sexual harassment and gaslighting.
  • Gabriel: "This isn't just inappropriate. This is actually super creepy. The guy needs to be put in his place and iced out for sure." (07:18)
  • Jordan compares Saul’s emotional maturity to a "12 year old boy with a TBI." (06:39)
• Boundary-Setting:
  • The hosts strongly advise the listener to cut off Saul with clear, immediate boundaries, not to stir up family drama (e.g., don’t contact his brother), and not to seek closure through repeated contact or long-winded letters.
  • Jordan: "The most effective way to deal with somebody like this, the least dramatic way, is to just draw a hard boundary and actually stand by it..." (16:44)
• Processing Mixed Messages:
  • Gabriel and Jordan explore why the listener sent mixed signals—writing a detailed letter but then texting “Happy Birthday.”
    • "Her inconsistency around Saul might be informed by a number of things, including her difficult history with men... But one of those things might just be this fundamental ability to hang in the awkwardness of being in conflict..." – Gabriel (19:57)
• Healing & Trust:
  • Trusting men after traumatic betrayal is a process, built by accumulating experiences with better boundaries and different people.
  • Gabriel: "Standing up to a creep and a bully in your professional group is one great way... To show yourself that you can withstand the distress, you can survive that..." (24:22)
• Personal Growth:
  • Painful as it is, the interaction with Saul can serve as a powerful lesson in boundary-setting and self-trust.
  • Jordan: "In a way, I'm happy you had to deal with him finally. Because I think this dude has laid bare some really important stuff for you. Painful? Absolutely. But very important." (26:19)

Notable Quotes:

• "Calling someone an opossum's anus is never not going to make me laugh. Sorry. What a weirdo." – Jordan (11:27)
• "You want to approach this conflict without creating a major gossip worthy scene. That is how you do it." – Jordan (16:44)

Key Timestamps:

• [06:33] – Listener’s situation with Saul
• [07:18] – Creepiness escalates
• [13:01] – Fallout after contacting Saul's brother
• [16:44] – Boundary-setting advice
• [21:47] – Navigating trust and closure

3. Listener Question #2: Supporting a Friend in a Mental Health Crisis

Letter Excerpt:

• Listener is worried about “Mary,” a former caretaker turned friend who had a breakdown after her much younger husband’s affair. Mary’s behavior includes threatening him, a suicide attempt, refusal to seek help, obsessing over a harassing “other woman” who may have poisoned her dog, and ongoing severe depression. The writer feels overwhelmed but guilty stepping back, and asks about her responsibility.

Key Insights & Advice:

• Recognizing Limits as a Friend
  • Jordan: "There's only so much you can do. She's literally saying, I won't involve the police, I will not get medical help, I will not go to therapy. Okay." (34:43)
• Constructive Confrontation & Boundaries
  • Have a candid, compassionate conversation with Mary: ask what she actually wants from the writer, set clear boundaries between being an empathetic ear and a problem-solver.
    • "What would you like from me? What would be most helpful?... If you're ready to open yourself up to help and pursue that help, I'm here to help you do that. But if you're not ready for that, then I'm going to have to pull back and let you figure this out..." – Jordan (35:13)
• Subtle Middle Ground
  • Gabriel: "That is the middle ground between stepping in hard and stepping back completely." (38:30)
• When to Intervene
  • Only intervene directly or call authorities if Mary is in immediate danger (e.g., during an active suicide threat).
• Taking Care of Self
  • The listener’s own grief over losing her father and caring for her family comes first.

Notable Quotes:

• "How do I love someone without compromising myself? How do I protect somebody without taking away her agency?" – Gabriel (39:25)
• "I hope that helps you keep an eye on the priorities here." – Jordan (40:36)

Key Timestamps:

• [29:28] – Situation with Mary
• [35:01] – How to talk to a friend in crisis
• [38:30] – Finding the “middle ground”
• [39:53] – When to intervene in a crisis

4. Listener Question #3: Employer Dodging Sick Leave & Stalling Salary

Letter Excerpt:

• Listener’s boyfriend, a long-term “best employee” at a small NY business, wants to switch from hourly to salary. Boss drags feet for months, refuses to comply with sick leave laws, and rebuffs requests for back pay. Department of Labor recommends filing for wage theft, but boyfriend fears retaliation.

Key Insights & Advice:

• Legal and Practical Context
  • Guest HR expert Joanna Tate outlines FLSA rules and NY state law: many jobs are required by law to be hourly, and sick leave must be provided unless the company is tiny.
  • Jordan: "Whether a job is paid on hourly basis or as a set salary, that isn’t just something a boss arbitrarily decides..." (42:51)
• Documentation & Leverage
  • Document all interactions; get any salary agreement in writing.
• Taking Action
  • Consult the free lawyer from Department of Labor.
  • Consider organizing with coworkers for leverage.
• Risks and Valuation
  • Filing a complaint is righteous but may mean having to leave the job.
  • Jordan: "Your boyfriend needs to do the math on what's more valuable to him: the sick pay, the stolen wages, or this job that he loves and the new salary..." (48:19)

Notable Quotes:

• "You’re not valued like that. We value you with mere words around here." – Jordan (41:22)
• "If the boss owes him like 30k, I would confront the boss and get the money and find a new job. But I don't know, if it's 5k and he loves his job, it's a different story." – Jordan (48:19)

Key Timestamps:

• [41:02] – Work situation described
• [42:51] – Legal context & employer responsibilities
• [47:48] – Practical risks & advice

5. Listener Question #4: Supporting a Struggling Parent Without Enabling

Letter Excerpt:

• Listener’s father lost millions in 2008, divorced, moved continents, and has spiraled through a series of “magic bullet” projects that never work out. Now nearing 63, the father’s resources and health are declining. Should the listener continue to support him emotionally, financially, or through coaching—or pull back?

Key Insights & Advice:

• Acknowledging Grief and Reality
  • Jordan: "It's also an interesting set of questions that he's asking... Let's start by appreciating what a sad predicament your father is in and what a predicament he's put you and your brother in... In a big way, I feel for your dad here." (61:32)
• Recognizing Limits & Responsibility
  • Don't encourage ungrounded business ventures or schemes; financial or practical support should be careful and bounded.
  • Only help if father meaningfully takes responsibility and acts realistically.
• Withdrawing Emotional “Inflation”
  • Gabriel: "I'm not sure that you should believe in your father, even if he doesn't believe in himself. I think that's his job." (72:36)
• Focus on the Listener’s Growth
  • Accepting parental limitation is a form of grief, and the listener’s job is to process that rather than endlessly “propping up” his father.
  • Jordan: "The best thing you can do, in my view... is to love your father, support your father, accept your father without compromising yourself financially, emotionally, practically..." (75:32)

Notable Quotes:

• "There's so much is riding on the next big idea. His safety, his power, his stability, his identity..." – Jordan (64:03)
• "Your dad, warts and all. That is something worth believing in. But maybe the even more helpful question for you is if it does feel true that you should believe in your father when he doesn't believe in himself, why is that?" – Gabriel (74:03)

Key Timestamps:

• [55:00] – Background: Father’s financial/motivational odyssey
• [61:32] – Emotional and practical toll on the son
• [72:36] – Should you “believe” in your parent?

Notable Quotes & Memorable Moments (with Timestamps)

• "This guy sounds like a 12 year old boy with a TBI trying to hit on the girl sitting next to him in algebra. What's wrong with this guy?" – Jordan (06:39)
• "Calling someone an opossum's anus is never not going to make me laugh. Sorry. What a weirdo." – Jordan (11:27)
• "How do I love someone without compromising myself? How do I protect somebody without taking away her agency?" – Gabriel (39:25)
• "I'm not sure you should believe in your father, even if he doesn't believe in himself. I think that's his job." – Gabriel (72:36)

Natural Flow & Tone

The tone alternates between sharply witty and deeply empathetic, with candid acknowledgment of trauma, frustration, and the sometimes absurd realities of human relationships. Both Jordan and Gabriel challenge listeners to face uncomfortable truths about responsibility and boundaries, often with self-deprecating humor, edgy analogies (“preeminent platypus perineum”), and blunt language.

Segment Timestamps

| Topic | Timestamps | |--------------------------- |-------------------| | Show Intro and News | 00:49 – 04:23 | | Creep/Manipulation Letter | 05:21 – 26:28 | | Mary’s Mental Health Crisis| 29:28 – 41:02 | | Workplace/Sick Leave | 41:02 – 52:38 | | Supporting Struggling Dad | 55:00 – 75:32 |

Takeaways

• Firm, clear boundaries and self-protective actions are crucial when dealing with manipulative or boundary-crossing individuals—regardless of guilt, history, or hope for closure.
• Supporting friends with mental health or crisis issues requires care, but also recognition that you cannot “save” someone who will not accept help.
• Legal and professional matters need documentation and knowing your true leverage.
• With chronic family dysfunction, loving support is best delivered without self-sacrifice or enabling.