The JTrain Podcast – “How do I approach men at the gym? - MONDAY MAILBAG”

Host: Jared Freid
Episode Date: October 6, 2025

Episode Overview

This episode is a classic "Mailbag Monday," where comedian Jared Freid tackles listener-submitted advice questions, mainly around dating, relationships, and modern life dilemmas. Jared dissects two main questions: one from a listener who joined a regular gym to meet men but feels out of place, and another from a woman concerned that her long-term boyfriend is failing “the dad test” based on how he’s handling their new dog. With candid, humorous reflection, Jared offers advice that cuts through surface-level concerns to address deeper issues.

Key Discussion Points & Insights

1. Audience Letter: Meeting Men at the Gym

[01:50–19:00]

• Listener Situation:

  • 33-year-old single woman in Manhattan.
  • Switched from a Pilates studio (female-centric) to a regular gym to meet men “in the wild.”
  • Feels uncomfortable and out of place, missing her Pilates reformer.

• Jared’s Take on Dating “in the Wild” Versus Dating Apps:

  • Societal Pressure: “There is this… it’s hard, it’s difficult because people want to meet people in real life... they want to feel like, you know, they didn’t need the apps.” [04:40]
  • Dating apps provide constant dopamine hits and matches—real life doesn’t offer the same frequency or instant gratification.
  • Going out and not meeting anyone isn’t a failure—“that is a normal night out.” [07:10]

• Challenging the Listener’s Premise:

  • Jared disagrees with the idea that being in “female-centric” spaces was her main dating obstacle:
    • “I think blaming your singleness on being in female-centric places, I disagree with the premise.” [10:25]
    • Chasing straight-line logic (“go where the men are”) is often a red herring.

• On Making Yourself Less Happy to Meet Men:

  • Listener now works out somewhere that makes her less happy and feels lost.
  • “You’re doing a workout that you don’t like and don’t know how to do, in order to meet men in a space that you would never go to in the first place if there weren’t men there.” [12:30]

• Jared’s Actionable Advice:

  • Rather than forcing herself into environments she dislikes, she should double down on spaces she loves (Pilates).
  • Build friendships and social circles around her core interests.
  • “You need the tribe… that’s what helps you find your person. I think digging into the things you like and love and finding people who also like and love those things are the ones who will be the Sherpa that hold your hand towards the person that you’re meant to be with.” [13:30]
  • Hosting group events through her Pilates community (a “Pilates Night Out”) expands her chances organically.
  • Notably, single or married women may have connections to other single men—don’t underestimate “friend-of-a-friend” pathways.

• Alternative: If You REALLY Want to Approach at the Gym:

  • Jared offers a few openers if she insists:
    • "Hey, what are you working on today?"
    • "Hey, I like your shoes, where did you get those sneakers?"
  • But reiterates, “I don’t think that’s the advice that helps you.” [15:25]

Memorable Quote

“I don’t want to go on a date with someone who is alone at the gym, not really happy, and not doing a workout they like. I would much rather go on a date with someone who has a full group of friends… really happy with that part of their life.”
— Jared Freid, [14:15]

2. Audience Letter: The “Dad Test” Dog Dilemma

[22:40–End]

• Listener Situation:

  • 25-year-old woman, with boyfriend since age 19, living together since 23.
  • Adopted a dog; concerned her boyfriend’s lackadaisical attitude toward the dog’s needs (e.g., not filling water bowl) signals he might fail at fatherhood.

• Initial Reaction to Dog/Fatherhood Leap:

  • “You’re writing to a 40-year-old man who’s never been married, no kids… and you’re like, ‘We’re 25 and living together…’ You are more of an adult than me!” [23:15]
  • Jared finds the “dad test” jump a bit drastic—“failed the dad test—wait, that sends a little bit of a shiver down my spine.” [23:25]
  • Observes that the listener seems to be seeking very definitive evidence, possibly prematurely.

• Breaking Down the Complaint:

  • Boyfriend gives dog more empathy/space in bed than her.
  • He doesn’t instinctively notice/fill water bowl, just feeds.
  • Listener connects these annoyances to bigger “dad” red flags.

• Jared’s Core Feedback:

  • Sees the pattern of taking small, typical relationship annoyances and escalating them to “moral” indictments (e.g., bad at fatherhood).
  • Modern arguing: “You’ve used a big word and made this into more than just a lazy boyfriend who won’t move over, which it could be. But when you go straight to that, that is an argument you’re trying to win, not a negotiation you’re trying to have.” [28:20]

• Root Causes & Relationship Dynamics:

  • He suspects the listener is having doubts about her relationship overall—possibly cold feet as things become more serious:
    • “To me, none of this has to do with the dog. None of this. I think you've come to me with trivial sitcom, tropey, relationship nuisances, and those are all something you're entitled to have.” [25:40]
    • “I believe based on this email, you're on the – you're getting cold feet in the relationship.” [31:40]

• On Jumping to Morality:

  • Jared discusses how people now often escalate minor issues into broad claims about right and wrong, making things harder to productively negotiate.
  • Advises her to keep things in “I” terms, share irritation with her boyfriend, and try to negotiate rather than “win.”

• Family Story Perspective:

  • Jared shares an anecdote about his own father (who played golf and left his mom home with young children) to illustrate that not sweating or over-moralizing the “little stuff” can work out just fine.

Memorable Quotes

“When you make the water bowl being bone dry into he might not be a good dad, you’re trying to find very solid reasons to not be with him that he has no say on.”
— Jared Freid, [32:50]

“My dad wouldn’t have filled the water bowl… Was he a bad dad? I don’t think so.”
— Jared Freid, [37:10]

Notable Quotes & Moments

• On Real-life Dating:
  “Those app meetings are false. They’re the mirages. They’re not real.” [08:40]
• On the Listener’s Gym Logic:
  “You’ve created a bigger mountain for yourself while thinking you’ve created a smaller one.” [13:10]
• On Relationship Negotiation:
  “You’re living in a closed space. You’re annoyed. That’s okay… When you do get married and he’s a bad dad and you go, I should have known, he never filled the water bowl… This is my fault. Like, you’re trying to get ahead of disappointment, which I don’t think you can really do.” [29:05]
• On Self-Awareness in Dating:
  “Be at the gym you want to be at… Create a community. Those people. Now you guys go out together, you got a crew. Maybe you meet single women… Maybe you meet married women who have husbands who are your best option for meeting new men.” [17:20]

Episode Structure: Timestamps

• 00:00–01:50 – Intro, show logistics (ads, tour dates, Patreon)
• 01:50–19:00 – Email #1: “How Do I Approach Men at the Gym?”
  • [04:40] – Dating in the wild vs. apps
  • [10:25] – On blaming “female-centric” spaces
  • [13:10] – On building community, not hunting men
  • [15:25] – How to approach at the gym (if you must)
• 19:00–22:40 – Ad/Break
• 22:40–End – Email #2: “Will My Boyfriend Be a Bad Dad Because of the Dog?”
  • [23:25] – On the “dad test” framing
  • [28:20] – Minor annoyances vs. moral arguments
  • [31:40] – Are you just having cold feet?
  • [37:10] – The ‘golf dad’ story and generational perspective

Takeaways & Final Thoughts

• Don’t abandon your passions, communities, or comfort just for the potential of meeting a romantic partner; instead, leverage your authentic social circles and let connections come more organically.
• Raising small annoyances to the level of moral “red flags” can block honest negotiation and partnership—keep arguments specific, collaborative, and grounded in how you feel, not how you judge.
• It’s normal to feel doubt or cold feet as relationships get more serious; don’t try to manufacture “legit” evidence for breakup anxiety.
• Jared’s candid comedic honesty is consistent, often self-deprecating, and always focused on practical emotional wisdom: dig deeper, ask what truly matters to you, and avoid chasing conventional wisdom if it makes you miserable.

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