The JTrain Podcast – "How Do I Make My Situationship a Relationship?"

Host: Jared Freid
Date: January 5, 2026
Episode: Monday Mailbag

Episode Overview

In the first Monday Mailbag of 2026, Jared Freid brings insightful, tough-love advice to listener questions on relationship expectations, tricky situationships, and friend group social finance dilemmas. With his signature comedic warmth, Jared dissects nuanced predicaments around commitment, authenticity, and the realities of adult friendship and romance—all delivered with his familiar blend of relatable humor and actionable guidance.

Key Discussion Points & Insights

1. Classy vs. Tacky – Should You Judge Your Friends’ Decisions?

[10:15–22:40]

• Listener's Dilemma: The emailer wonders whether to call out friends for "tacky" choices—particularly a friend's engagement ring—or keep thoughts to themselves.
• Jared’s Insight:
  • He unpacks the difference between opinions and objective truths regarding taste.
  • Shares that unless asked for an opinion (or if the friend notices your lack of excitement and asks), it’s better to stay quiet.
  • Emphasizes that what matters is whether the ring is meaningful to the person wearing it—not to outsiders.
• On Being Asked for Input:
  • Only probe deeper ("Did you ask her what she wanted?") if the friend appears insecure or directly seeks input.
  • Giving unsolicited advice about taste is “tacky” in itself.

Notable Quote:

“I think it’s tacky to then go back to this friend to say, ‘Hey, I’ve been thinking about the ring...I think you better scratch that ring...’ It may be that’s her taste. So the questions should be along the lines of, ‘How did you go about getting it?’”
— Jared Freid [19:55]

2. “How Do I Make My Situationship a Relationship?” – The Long Distance Dilemma

[29:15–49:25]

• Listener's Story:

  • Two-year long-distance situationship.
  • She’s in her 30s, he’s 47 (never married, no kids). He’s been clear about not wanting a relationship. She continues hoping for more.
  • Now dating someone else (kind, consistent) but still yearning for “Ryan” (the situationship guy).

• Jared’s Analysis:

  • Pinpoints that only the person seeking more labels it a “situationship.”
  • Highlights that all time spent with Ryan is “vacation mode”—not reality, never facing the real-life logistics of commitment.
  • Recognizes EVERYONE in this triangle is hurting: the emailer (chasing potential), the current boyfriend (playing backup), and Ryan (having to repeatedly state his boundaries).

• Advice Given:

  • End it with the current nice/consistent boyfriend to avoid stringing him along.
  • Confront Ryan directly when he visits:
    • Clearly state desire for an actual relationship (potentially involving moving cities).
    • Be prepared for a no—because he will likely reiterate his lack of interest in commitment.
    • Afterward, cut contact entirely (including unfollowing on social media) to properly move on.

Notable Quotes:

“You have rated Ryan based on potential. The actuality is this is someone who isn’t ever going to be what you want them to be.”
— Jared Freid [34:23]

“You need to kind of respect my space because I’m a little bit like an addict right now. I need to get off of this thing, this idea, this dream future I’ve concocted.”
— Jared Freid [46:10]

3. Social Finances with Friends – Venmo, Awkwardness & Wealth Disparity

[52:20–61:40]

• Listener's Dilemma:

  • Feels awkward reminding friends to pay their share for group orders (e.g., pizza), especially since they earn more money.
  • Worries about being perceived as rude or stingy.

• Jared’s Guidance:

  • Most anxieties are internal—people care more about not being “the cheapskate” than about how much you make.
  • Suggests solving the issue at its root:
    • Stop offering to pay for everyone up front.
    • Handle payments and Venmo requests promptly, in the moment, rather than after the fact.
    • Lessen time between payment and reimbursement to reduce discomfort.

Notable Quote:

“Let’s not put this off. The time between is adding to your anxiety. If you make a promise to yourself that anytime something’s paid for, we do it now, all of this goes away.”
— Jared Freid [58:40]

Memorable Moments & Jared’s Signature Tone

• Kicks off the episode with gratitude and energetic encouragement for listeners’ New Year’s resolutions. [01:15]
• Repeats his advice ethos: “Bring in for the hug, whisper some hard truths into your ear.” [02:00]
• Injects self-deprecation and candor about his own single status and boundaries (not married, no kids, just like several listeners). [33:40, 38:10]
• Gently rebukes the “drug dealer/addict” dynamic that happens in drawn-out situationships. [44:30]
• Advises listeners not to let social media fuel false ideas about what “could have been.” [50:55]

Timestamps for Key Segments

• Intro, Housekeeping, Tour Updates: 00:00–08:10
• Classy vs. Tacky Ring Advice: 10:15–22:40
• Situationship Story Breakdown & Advice: 29:15–49:25
• Venmo & Social Finances Dilemma: 52:20–61:40

Episode Takeaways

• Don’t project your opinions on what’s “tacky” or “classy” unless invited—they’re subjective, and unsolicited advice is usually unwelcome.
• Situationships are rarely changed by one more declaration; listen to actions and words for what they are, not what you wish they could be.
• Drawing clear boundaries and direct communication, even if hard, is the kindest and most respectful move for everyone involved.
• With money and friends, upfront clarity and direct (immediate!) action ease awkwardness more than overthinking or delay.

For more mailbag advice, to submit your own question, or to see Jared live, follow @jtrainpodcast on Instagram and subscribe for updates.