The JTrain Podcast - Mailbag Monday: "I'm 41 And Getting A Divorce! What's Your Best Advice?!"

Host: Jared Freid
Date: January 19, 2026
Episode Type: Monday Mailbag - Listener Questions

Episode Overview

In this Mailbag Monday episode of The JTrain Podcast, comedian Jared Freid fields listener emails covering sports betting advice for the Super Bowl, navigating social obligations in relationships, and—most centrally—guidance for a 41-year-old woman embarking on single life and dating after divorce. Jared infuses his responses with warmth, directness, and humor, blending practical advice with relatable, comedic takes on modern life challenges.

Key Discussion Points & Insights

1. Fun and Responsible Super Bowl Betting

[10:30 – 24:10]

• Question: How can a Seahawks fan bet on the Super Bowl and keep it light and casual, without getting too emotionally invested?
• Jared’s Advice:
  • "Only bet what you're willing to lose." The fun stops when it gets serious—i.e., never risk rent money on a game.
  • Public teams vs. sharp betting: Seahawks aren’t a loud ‘public’ team, so odds may be more favorable.
  • For keeping it fun:
    • Bet small amounts—enough to buy an “adventure.”
    • Bet on your favorite player (e.g., “anytime touchdown scorer” bets are low-pressure and fun).
    • Try obscure, high-odds bets like “will there be a safety?” for extra excitement.
    • Navigating betting apps can be tricky; ask someone to show you where the fun bets are.
  • Sports Bar Etiquette: Be a respectful fan—even when surrounded by rivals. Jared recommends the “head nod” to fellow fans instead of boastful behavior.
  • Memorable Quote:
    • “The minute you go from fan to fanatic is the minute you’ve kind of lost the narrative.” (Jared, 23:20)
  • On Family Loyalties:
    • Jared addresses his allegiance shift to the Bears (where his brother works) over his childhood Patriots:
      • "The idea that anyone would be surprised that I would cheer for the Bears, I would say to that person: seek therapy." (Jared, 27:35)

2. Navigating Relationship Social Circles in Adulthood

[27:40 – 44:30]

• Question: A 25-year-old listener feels pressure to “show face” and bond with her boyfriend’s friends’ girlfriends after moving back to a college town. She’s exhausted and would rather prioritize her own friends and self-care.
• Jared’s Breakdown:
  • Acknowledges how forced camaraderie can feel draining, especially when it stems from tenuous college connections (“our boyfriends once blacked out together…”).
  • “...Do I really have to, like, now engage with this girlfriend in a way that's serious?”
  • Contrasts male friendships with more “depthy” female friendships—explains why the latter may feel more demanding.
  • Offers insight: At 25, big group hangs are normal, but it’s okay to be selective and honest about your limits.
  • Advice for Communicating with Partner:
    • Suggests sharing the well-written email or even this segment of the podcast with her boyfriend.
    • Encourage “more local than national” hangs—smaller, more meaningful gatherings with closely connected friends preferred over big exhausting group events.
  • Memorable Quote:
    • “You want to be more local than national.” (Jared, 43:00)
  • Suggests coaching partner on how to introduce her to new people in a more enjoyable, less socially draining way.

3. Dating After Divorce at 41: Advice for Starting Over

[46:00 – End (~55:00)]

• Question: A 41-year-old woman is newly divorced, moving to a bigger city, starting a new job, and has hardly dated before, but wants to approach dating without looking for anything serious. Is admitting that off-putting to men? How to proceed?
• Jared’s Response:
  • First, commends her for all the life changes:
    • “You just did a whole lifetime in one sentence.” (Jared, 46:35)
  • On Telling Men You Want Something Casual:
    • “A woman saying she's not looking for anything serious is like you cutting, taking a knife to your palm, smearing a bunch of blood and then jumping into an ocean full of sharks.” (Jared, 47:00)
    • Not a “bad” thing, but a flag to be wary: Many men will hear “casual” as “easy sex,” not “fun makeouts and no pressure.”
  • Key Advice:
    • Don’t say “I’m clueless” or put yourself down—you’re new to dating, not life.
      • “Stop saying I'm so clueless. Stop it... You're not new to earth. You're new to dating.”
    • Don’t advertise “casual” up front; say you’re looking for the right connection and see where it goes.
    • Keep standards high (e.g., expect a proper date, good conversation, affection, but on your own terms).
    • Protect your experience: Don’t let the floodgates open to men just looking for an easy hookup because you’re “the new divorcée on the scene.”
  • Scenario for Minimum Acceptable Date:
    • “He brings you in, you have a soft kiss that turns into a more passionate kiss. You two go home, you say, 'maybe I shouldn’t, I don’t know.' …You go for dinner again… That’s what you want and you deserve it.” (Jared, 49:00)
  • Dating Like a Dude:
    • “Start dating like a dude. I'm just looking to meet someone and see if it's the right connection. That's it.” (Jared, 54:10)

Notable Quotes & Memorable Moments

• Sports Fandom Sanity:
  • “Fan is a derivative of fanatic. So remember that: fanatic is a crazy person.” (23:10)
  • “If you’re as crazy about politics as you are with your team... go seek therapy. You are the problem.” (27:15)
• On Socializing with Boyfriend’s Friends’ Girlfriends:
  • “It is less socially exhausting to, ‘hey, let’s go out with my really close friend and his girlfriend who’s new to the area...’ But you don’t want to be stuck at grand parties with 10 strangers.” (42:15)
• On Reframing Dating after Divorce:
  • “Don’t say you’re looking for casual. Don’t widen your dredge…” (53:25)

Timestamps for Important Segments

• 10:30 - Listener question: Super Bowl betting for casual fans
• 14:00 - Advice on prop bets and casual ways to make the game fun
• 23:10 - Rant on sports fandom, family loyalty, and “fan vs. fanatic”
• 27:40 - 25-year-old listener struggles with social obligations
• 39:15 - Analysis of friendship dynamics, gender differences in socializing
• 43:00 - Communication advice for couples dealing with group hangouts
• 46:00 - 41-year-old divorcée asks for dating advice
• 47:00 - Warnings on how “casual” can be misinterpreted by men
• 49:00 - Jared outlines the “minimum standard” date
• 54:10 - Closing thoughts: Date like a dude, keep your standards

Overall Tone & Takeaways

Jared keeps the tone lively, empathetic, and laced with his trademark wit. He offers honest, slightly cautionary advice, especially for listeners entering unfamiliar territory—whether it’s sports betting or post-divorce dating. The episode manages to balance entertainment with meaningful, actionable insight, encouraging listeners to know themselves, guard their boundaries, and not lose the fun in the process.

For Listeners Who Didn’t Tune In

• Expect advice that’s as funny as it is practical, especially for anyone navigating new adult experiences—be it betting, adult friendships, or starting over romantically.
• Jared’s metaphors and stories make ordinary dilemmas feel both relatable and laugh-out-loud funny.
• The episode helps listeners feel less alone in their awkward questions and more equipped to take the next step with confidence.