The JTrain Podcast: Should I Text A Guy I Matched With Two Years Ago? – MONDAY MAILBAG

Hosted by: Jared Freid
Episode Date: November 17, 2025

Episode Overview

This Mailbag Monday episode finds Jared Freid in a Durham, NC hotel, tackling three new listener advice emails on modern dating, friendship obligations, and making big moves in life. Jared offers his signature blend of humor and candid insight, focusing especially on the pitfalls of wishful thinking in old dating-app connections, managing expectations from friends in crisis, and embracing personal adventure.

Key Discussion Points & Insights

1. Should I Text A Guy I Matched With Two Years Ago?

Listener dilemma: Reaching out to an old dating app match when visiting his city

• Situation Recap:

  • Listener matched with a guy while both were visiting the same city, never met but formed a text connection.
  • His profile was clear about wanting something casual; she realized she wanted more and cut contact.
  • Two years later, she’ll be in his city for work and wonders if she should reach out, hoping maybe things have changed.

• Jared’s Analysis:

  • Jared stresses the importance of taking people at their word, especially when someone says they want something casual.
  • “If he says on the dating profile he wants casual, believe him.”
    — Jared, 07:45
  • Notes that the listener writing “we live a six hour drive apart” is a subtle sign of hoping it could be more—she’s writing to justify the possibility to herself.
  • Predicts if she reaches out, she risks getting emotionally attached all over again to someone for whom nothing has changed.
  • Draws an analogy between old romantic fantasies versus modern realities: falling for a connection you can't or shouldn't try to force into permanence.
  • Jared’s advice: Only reach out if you’re truly content with it being casual. Otherwise, “You have to wait for him to come to you.”

• Actionable Recommendation:

  • If compelled to text:
    “Hey, I know it’s been two years, but I’ll be in town for work soon. If you’re up for getting a drink, let me know. I’m still single, not sure where you’re at or what you’re looking for.”
    — Jared, 18:40
  • Final caution:
    “I’m here to warn you. I’m just here to try and protect someone that, you know… I just know what's going to happen.”
    — Jared, 19:15

2. Overwhelmed by Friends’ Big Life Changes

Listener dilemma: Two best friends needing support—one divorcing, one becoming a single mom—as the listener handles their own demanding life

• Situation Recap:

  • Listener is child-free and partnered, but anxious about being counted on heavily by two close friends facing major life changes.
  • Works full-time and is part-time caregiver for parents.
  • Worries about being “expected to fall into a ‘partner’ role.”

• Jared’s Analysis:

  • Jared acknowledges how communal support is common (and beautiful) among women, but also sees the emotional weight and anxiety this uncertainty creates.
  • “Easy there, big fella… You are presented with vague future. There’s nothing scarier than ‘I’m gonna need your help.’”
    — Jared, 33:13
  • Uses a metaphor from How I Met Your Mother: waiting for a symbolic “slap” you’ve been warned about is worse than the slap itself.
  • Emphasizes the psychological dislike of open-ended, unspecific demands.
  • Encourages listener not to assume friends are including her in their actual parenting or divorce logistics; likely, their needs are more normal than feared.

• Actionable Steps:

  • Be proactive: arrange a drink or conversation before the problems hit.
  • “Hey, I know you mentioned you’ll need my support. Of course I’m here for you, but it’s giving me a bit of anxiety—can you clue me in on what you were thinking? I want to make sure I’m there for you, but I have my own things going on.”
    — Jared, 42:08
  • “Now you’re literally sitting at a table negotiating, and that’s what friendships and families are. Negotiations.”
    — Jared, 43:01
  • “I don’t think your friend factored you into the parenting of this child. That would be very weird and not a great thing to do.”
    — Jared, 40:22
  • Core advice: Clarify and set boundaries early to avoid anticipatory anxiety.

3. Should I Move Just for Me?

Listener dilemma: Moving from a small Tennessee town to Fort Myers, FL just because she wants to

• Situation Recap:

  • 35, single, teacher, ended an engagement, helping aging parents, not close to family.
  • Visited Fort Myers, loved it, felt emotional leaving.
  • Moving would be challenging—higher rent, more demanding job—but do-able; no person is motivating the move except herself.

• Jared’s Analysis:

  • “You’re 35 and you deserve an adventure.”
    — Jared, 57:18
  • Shares his own story of moving from New York to Florida and how the right turn improved his creativity and health.
  • Recognizes pain points (distance from family, less comfort), but highlights emotional fulfillment and the need for newness.
  • “This isn’t a person I’d be moving for. I’d be moving for me. Beautiful.”
    — Jared, 58:31
  • “I’m almost a little emotional reading this email. I’m happy for you... you can do anything for a year and come back. What’s the worst that could happen?”
    — Jared, 59:01
  • Encourages embracing the move and emphasizes that if it doesn’t work, she can always return.

• Actionable Steps:

  • Go for the move: “Do it. Congratulations on the move.”
    — Jared, 01:00:06

Notable Quotes & Memorable Moments

• On dating-app connections:
  “Where your stuff lies—you act differently than where your luggage lies.”
  — Jared, 03:40
• On wishful thinking:
  “No box for him overtakes being honest that he wants to be casual.”
  — Jared, 15:58
• On managing friendships:
  “Easy there, big fella… Let me get you a little bit rested here because I think you are in a spiral and I mean that in a very caring way.”
  — Jared, 33:18
• On moving for yourself:
  “We’re all just kind of floating through this thing… just trying to have a nice hour.”
  — Jared, 58:52
• Reflecting on life: “Everything happens for a reason. Everything happens for the best.”
  — Jared, 01:00:15

Key Timestamps

• Mailbag Monday Format and Show Intro: 00:00 – 03:00
• Email 1: Should I Re-Contact the Casual Guy? 03:00 – 20:00
• Email 2: Friends’ Major Life Changes and Emotional Boundaries 26:45 – 46:00
• Email 3: Moving for Yourself – Fort Myers Decision 57:10 – 01:00:45

Episode Tone & Style

Informal, empathetic, and humor-laced, Jared keeps the show conversational and real, blending practical advice with self-aware jokes and personal stories. He delivers both validation and challenge to listener perspectives, aiming for honesty but never cruelty.

Summary Takeaways

• Take people at face value and don’t attempt to rewrite history or intentions—especially with old dating-app flames.
• Candid conversations and boundaries quell anxiety about helping friends through tough times.
• If a new adventure calls and isn’t for anyone but you, seize it—and remember, nothing’s permanent.

For more advice or to submit your own Mailbag Monday question, email jtrainpodcast@gmail.com.