The JTrain Podcast: "I Gave a Guy My Number a Week Ago! When Do I Move On? Help!"

Host: Jared Freid
Date: December 15, 2025

Episode Overview

This Mailbag Monday episode centers around Jared Freid answering listener emails and DMs about modern relationship dilemmas—ranging from emotional boundaries in marriage, dating confidence, to friendship group dynamics. Jared offers candid, empathetic, and often humorous advice, aiming to provide clarity and support for each listener’s predicament. The bulk of the episode is made up of three main listener questions, each tackled with Jared’s signature blend of logic and emotional understanding.

Key Discussion Points & Insights

1. Emotional Boundaries in Marriage: The "European Friend" Email

(Starts ~08:00)

Scenario:

A listener’s husband has returned from a year-long overseas military assignment. One European woman he met continues to send him frequent, flirty texts (e.g., “I miss you,” hearts/winky faces, attempts to meet up, etc.), which makes the listener uncomfortable. The husband responds warmly, admitting he misses her too, but affirms his marital status and dodges meet-up invites, even on their anniversary.

Jared’s Analysis:

• Addressing Feelings Head-On: Jared encourages the listener to directly state their discomfort to their partner, suggesting, “European woman is messaging you a lot. It’s making me uncomfortable. End of sentence.”
  — Jared Freid, 10:10
• Binary Choices in Reactions: According to Jared, the husband’s response will reveal a lot:
  • Either he validates her feelings (“I get it, I’d be uncomfortable too”), or
  • He diminishes them (“You’re crazy, don’t be possessive”), a red flag in a relationship.
• Minimal Justification for Phone Checking: Jared empathizes with the choice to go through the husband’s phone, likening it to hitting a sibling after prolonged annoyance—imperfect, but understandable.
• On Boundaries: Once it’s confessed that “I miss you” is a regular message, Jared draws a boundary:
  “That’s a point where we have to say, ‘Hey, this has gone too far. I need to end our conversations because they’ve gone away that would upset someone else.’”
  — Jared Freid, 19:10

Notable Quote:

“You need to lose the perspective that you’re possessive. I don’t think you’re being possessive at all. I think you need to say your beginning sentence: the European woman that you’re texting with makes me uncomfortable. End it there. How does he fix that?”
— Jared Freid, 23:35

Advice Takeaway:

• You’re not “possessive” for having a reaction to flirty and excessive outside contact.
• Concerns in a relationship aren’t math problems—emotions matter.
• Save emotional labor—don’t over-explain or self-vilify for honest feelings.

2. Dating Confidence & "Moving On"

(Starts ~40:00)

Scenario:

A DM asks: “I gave a guy my number a week ago. He hasn’t reached out yet. Should I move on or give it a little longer? What other reasons would there be besides him not being interested?”

Jared’s Analysis:

• Context Matters: If it’s someone from a bar, “they’re not interested.” If it’s a coworker, potential workplace boundaries are the issue.
• Release the Outcome:
  “The minute you give the number, that’s when you move on. This idea…you need a bow on every situation? That is a low-confidence move.”
  — Jared Freid, 41:35
• Shop Owner Analogy:
  “You’re the shop owner. People come to your store, they take a look around, they buy something, or they leave. The door’s right there. You can come back anytime. I’ll decide if I’m open for your business or not.”
  — Jared Freid, 43:00
• Let People In or Out: If they text later (even a year), you decide then how to respond; you’re not beholden to the outcome.

Notable Quote:

“You made a boss ass move. You went up to someone, you gave them your number… Then you walk away. If they reach out, you’ll be fine when they do.”
— Jared Freid, 44:05

Advice Takeaway:

• Putting your number out there is the bold part—the rest isn’t your responsibility.
• Don’t get hung up on needing closure or a perfectly “clean ending.”
• Confidence from abundance: you can always move on.

3. Friendship Dynamics & Group Tradition

(Starts ~46:10)

Scenario:

A listener describes a long-standing monthly dinner tradition with three close friends (all women, now 35ish). One is a lesbian whose wife keeps pushing to be included in the dinners, despite the group tradition being “spouses stay home.” The wife is described as “a lot”—she gets drunk, dominates, and often cries at events.

Jared’s Analysis:

• Stick to Your Boundaries: Jared affirms that the group is allowed to set its own rules and that, “You don’t need to go into ‘she’s a lot.’”
  — Jared Freid, 48:30
• Simple Statement is Key:
  “Hey, this is a dinner we do with this group. This is the group. The group is established. Period. Done.”
  — Jared Freid, 48:55
• If Pressed, Stay Firm: If the friend says she can only come if her wife comes, it’s fair for the group to say, “That’s not what I signed up for.”
• Self-Care Angle: Stress that this time is “important to me…my mental health time…a satiating dinner.”

Notable Quote:

“I’m not looking to do, like, a Frankenstein version of this group dinner. We’re not bringing in the wives and husbands.”
— Jared Freid, 50:20

Advice Takeaway:

• Set boundaries for shared traditions.
• No need to over-explain—simple, assertive statements work best.
• You are entitled to spaces that feel rejuvenating and safe for you.

Notable Quotes & Memorable Moments (with Timestamps)

• "European woman is messaging you a lot. It’s making me uncomfortable. End of sentence. Breathe. There it is." — Jared Freid, 10:15
• "The minute you give the number, that’s when you move on. This idea you need a bow on every situation? That is a low-confidence move." — Jared Freid, 41:35
• "You made a boss ass move. ...Then you walk away. Go ahead. And I know I'm telling you how to feel right now. ...You're going to be fine." — Jared Freid, 44:05
• "Hey, this is a dinner we do with this group. This is the group. The group is established. ...Take a breath. Done." — Jared Freid, 48:30
• "I’m not looking to do, like, a Frankenstein version of this group dinner. We’re not bringing in the wives and husbands." — Jared Freid, 50:20

Structural Highlights

• Listener-centered: Jared affirms and appreciates each submitter’s vulnerability in writing in.
• Empathetic yet Direct Advice: Advice is often delivered with a balance of emotional support and matter-of-fact logic.
• Anecdotes & Relatability: Jared uses personal examples and analogies to clarify his advice and make listeners feel understood.

Useful Timestamps for Key Segments

• [08:00] – Start of "European friend" marriage question
• [19:10] – Jared’s boundary advice: “Hey, I really miss you, too...”
• [23:35] – Reassurance: “You’re not possessive...”
• [40:00] – “Gave a guy my number a week ago”—DM, main dating advice
• [43:00] – Shop owner analogy
• [48:10] – Friends dinner group email

Summary for New Listeners

Whether it’s navigating friendships, forging new romances, or defining boundaries in marriage, Jared Freid’s Mailbag Monday delivers direct, validating, and humorous advice. He encourages listeners to trust their gut, be confident in their boundaries, and let go of the need for perfect endings—reminding us all to give ourselves a little more credit and compassion in the muddle of modern relationships.