The JTrain Podcast – “My Boyfriend is Mad I’m Taking Ozempic” | MONDAY MAILBAG

Host: Jared Freid
Date: October 13, 2025

Episode Overview

On this Mailbag Monday episode, Jared Freid responds solo to listener emails, offering candid and comedic advice on relationships and life dilemmas. The episode’s main theme centers on vulnerability, support in partnerships, and self-awareness, most notably through a discussion about using Ozempic for weight loss, a boyfriend’s unsupportive reaction, moving on after a breakup, and navigating feelings for a work crush. Jared emphasizes empathy and honesty, consistently blending humor with heartfelt reflections on personal challenges.

Key Discussion Points & Insights

[06:15] Email #1: “My Boyfriend is Mad I’m Taking Ozempic”

Listener Summary

• Female listener shares decision to start Ozempic after lifelong weight struggles.
• Describes deep shame, internal “food noise”, and exhaustion from failed attempts at dieting.
• Upon revealing her choice to her boyfriend, he responds: “Oh, so you don’t want to diet and exercise? That’s the lazy way out.”

Jared’s Reaction & Analysis

• Instantly congratulates the writer for taking a challenging, vulnerable step:

  “Congratulations. That’s tough to do. … To go on Ozempic, you’re admitting that something might be beyond you.” [07:30]

• Deep dive into the psychological realities of food obsession and weight stigma:
  • “I watch thin people eat. That is a thing I do. I watch them like they are animals at the zoo.” [13:40]
  • Offers empathy: “You are speaking to my heart. This emailer is me as much as I am them. So I hope they feel seen.” [09:45]
• Explains societal misunderstandings about weight and food noise—a focus of his own standup.

On the Boyfriend’s Response

• Jared is blunt:

  “That is the dumbest fuck if that’s his opinion.” [19:33]

• Acknowledges that some people dismiss experiences they can't relate to, but still criticizes the boyfriend’s lack of empathy:

  “All mean judgments start with, they've never experienced or met someone with this plight.” [24:15]

Advice on Relationship Survival

• The real test is not logistical (ordering food), but emotional support and understanding.
  • “A relationship can survive this. I don’t think it can survive the lack of understanding how big of a thing this is for you.” [29:55]
• Urges the listener to evaluate:
  • Has she truly shared the depth of her struggle with her boyfriend?
  • If so, and he remains unsupportive, that’s a major concern for long-term compatibility.

Notable Quote

“If you have been deep with him about your eating and how you feel…it’s been this lifelong thing...then the response is concerning.” [32:47]

[34:50] Email #2: “Do I Have to Give My Ex’s Clothes Back?”

Listener Summary

• Writer’s ex-boyfriend broke up with her suddenly. He’s blocked. She wonders whether she should drive an hour to return his stuff.

Jared’s Advice

• “There is no winning in trying to win a breakup. You’re never going to win.” [36:18]
• Holding onto ex’s possessions is an emotional hazard:
  • “It will only remind you of the ex and the relationship and bring you to a place that you can't control.” [38:10]
• Logistics recommendation:
  • Bag up the clothes, arrange an easy pickup window, set a deadline for disposal:

    “Do it like you're the cable guy: ‘From 10am to 1pm a box of your stuff is going to be outside my garage. After that…it’s going to the garbage.’” [41:05]

  • Do not try to hurt or provoke the ex—focus on emotional closure.

[43:20] Email #3: “Five Years In, Crushing on a Coworker”

Listener Summary

• 27F, five years with boyfriend (27M), both in medicine, mostly long-distance, never lived together.
• She feels stale in her current relationship, develops a crush on a coworker.
• Wants to know if she should “hope it fizzles” or if it’s a red flag about her relationship.

Jared’s Analysis

• Work crushes easily bring excitement because they’re “new and exciting” and happen in an environment where you’re “getting paid to be there.” [46:23]
• Notes the importance of forward movement in a relationship (“Relationships are like sharks, they either keep moving or they die.”) [49:30]
• Suggests her current relationship may be “hovering” with no actionable plans, which breeds staleness and causes her to seek novelty elsewhere.
• Jared’s pointed advice:

  “Don’t confuse hope for a plan.” [54:10]

  • Hoping the crush “fizzles” isn’t a strategy.

Advice for the Listener

• Initiate a vulnerable conversation with her boyfriend about the staleness and lack of real steps forward:
  • “I feel like we’re just hovering. What are we doing here?”
• Urges her to reflect:

  “Do you have a boyfriend because you just like the security…or because there’s something special here?” [56:30]

• Reassures that ending the relationship at 27 with one partner is not the end of the world—she will be okay and find love again.

Notable Moment

• Jared empathizes with the challenge of ending a long-term relationship, shares self-aware, compassionate humor:

  “I hope my indecision on how to help you is helpful.” [01:00:10]

Notable Quotes & Memorable Moments

• “You are speaking to my heart. This emailer is me as much as I am them. So I hope they feel seen.” [09:45]
• “I think the real thing to wonder if it can survive is: can he see where you’re coming from?” [32:05]
• “There is no winning in trying to win a breakup.” [36:18]
• “All mean judgments start with, they've never experienced or met someone with this plight.” [24:15]
• “Don’t confuse hope for a plan.” [54:10]
• “Do you have a boyfriend because you just like the security…or because there’s something special here?” [56:30]

Timestamps for Key Segments

• 06:15 — Main Ozempic Email & Weight Struggles
• 19:33 — Reaction to Boyfriend’s Dismissive Comment
• 29:55 — Discussion on Relationship Survival & Empathy
• 34:50 — Returning Ex-Boyfriend’s Clothes
• 38:10 — Emotional Hazards of Keeping Ex’s Stuff
• 41:05 — Logistics of Returning Items
• 43:20 — Five-Year Relationship, Crushing on Coworker
• 46:23 — The Psychology of Work Crushes
• 54:10 — Distinction Between Hope & Planning for Relationships

Tone & Style

Jared delivers sincere empathy and comedic honesty, blending relatable personal anecdotes with practical advice. His style is direct, conversational, and at times, self-deprecating, designed to make listeners feel both entertained and understood.

For listeners seeking perspective on relationship struggles, emotional vulnerability, and navigating tough conversations with partners, this episode delivers a blend of humor and heartfelt validation.