The JTrain Podcast: "I'm Making A Dating App Profile! What's Your Number One Piece Of Advice?" – MAILBAG MONDAY

Host: Jared Freid
Date: December 1, 2025

Episode Overview

In this Mailbag Monday episode, Jared Freid, comedian and “the horse’s mouth” when it comes to dating advice, reads and responds to listener emails covering recent dating dilemmas, the challenges of starting a new dating app profile, and confronting patterns around casual versus committed encounters. Jared delivers his signature unfiltered, humorous, and practical perspective on modern dating struggles, offering advice rooted in honesty and self-awareness.

Key Discussion Points & Insights

1. Analyzing a “Guy from the Past” Situation

(Begins ~04:10)

• Listener’s Dilemma: A 32-year-old woman recounts going out for drinks (after a past make-out in their 20s) with a guy she went to high school with. While there was strong chemistry but no sex, the guy later texts expressing regret for the night escalating, saying he "values friendship" more and feels guilt over his behavior.

• Jared’s Reading:

  • The man's language is disproportionate to the situation, using intense phrases to create distance and avoid further romantic involvement.
  • "This is him pulling back... he's putting way larger words and descriptions on this to kind of fend you away to get you to, like, back off." (Jared, 10:55)
  • The sudden mention of moving to Costa Rica signals life confusion, not readiness for commitment—"If you're looking for serious, I think you gotta exit stage left." (Jared, 13:45)
  • Men from the past often reach out due to nostalgia, loneliness, or ego boosts, not necessarily genuine interest in a relationship.
  • Jared emphasizes the difference between a "great date" and a true "connection"—shared history (same high school) can manufacture comfort but doesn't guarantee compatibility.

Notable Quote:

“Men start at nothing and then jump ahead 30 steps from where you are. You're like, let's go on date, too. And he's like, she's gonna want date two and then day three, and then we're married, and then I'm stuck, and I don't even know if I like her. That's where he's at. He's freaking out.” (Jared, 18:07)

2. Entertaining Men Who Only Want Casual Sex

(Begins ~28:55)

• Listener’s Question: “How do I stop myself from entertaining men who only want casual sex?” She describes entering flirtatious or sexual texting with men, even when seeking a relationship, and expresses feelings of unworthiness due to body image.

• Jared’s Insights:

  • Most people you meet are open to casual sex; you can't control others’ intentions, only your own boundaries and desires.
  • "Anyone you entertain is in the game for casual sex... I'm sorry to inform you." (Jared, 29:20)
  • If sexting or sexual talk starts immediately, that's the track you're on—hard to backtrack to something serious after.
  • Self-worth struggles and body image shouldn't dictate what you settle for—Jared recommends finding confidence in one's own relationship goals and being forthright about them.
  • Practical Advice: Place “I want a relationship” front and center, communicate it early (“above the storefront”), and only engage deeper with those who reciprocate.

Notable Quote:

“You are looking with your dating app profile to shoo away people who don't like you and bring in people who respond specifically to your specifics. That gets you through all the boring, vague dating talk.” (Jared, 46:11)

Memorable Moment:

Jared affectionately reminds listeners that their appearance is "for someone," emphasizing that there’s “a butt for every seat.” He encourages, "You deserve what you want... You are entitled to that. You are deserving of that. You’re gonna find that." (Jared, 39:09)

3. Advice for Making a New Dating App Profile

(Begins ~43:15)

• Listener’s Problem: Starting a new dating profile feels depressing and overwhelming.

• Jared’s Response:

  • First, don’t bring negativity onto apps: “If it is depressing, the dating apps probably aren’t for you.”
  • Your attitude sets the tone—negativity attracts negative experiences and people.
  • Profile Building Advice:
    • First three pictures: solo, well-lit, no hats/sunglasses—“Bright, beautiful you.”
    • All prompts should be answered with “I statements”: be specific and personal. E.g., “Saturday nights I’m rewatching [show]; Sundays I get coffee at [place].”
    • The goal is to polarize on purpose—draw in your people, deter those who aren't a fit.

Notable Quote:

"Don’t go on the apps negative because you're going to meet people that are going to enrage you to your core. Perk up, buttercup. It's time to have a better attitude." (Jared, 44:20)

Notable Quotes & Memorable Moments

• On men reaching out to old flings just for comfort:

  “If you made out with us once, we think you'll make out with us forever. That is part delusion. That's part overconfidence, but that is just how a lot of men think.” (Jared, 16:05)

• On setting relationship standards:

  “The only thing you wrote that's controllable is ‘I want a relationship.’ That is, to me, that should go right above the storefront of you.” (Jared, 34:55)

• On the paradox of texting:

  “When you're texting with someone, you're hoping they're going to ask you out… But that’s not really a plan. The plan has to be, first, knowing your goals. Your goal is, ‘I want a relationship.’” (Jared, 41:25)

Timestamps for Important Segments

• Listener Email #1: Guy from the Past Analysis – 04:10 to 26:25
• Listener Email #2: Entertaining Men Seeking Casual – 28:55 to 42:00
• Listener Email #3: Dating App Profile Advice – 43:15 to 48:15

Tone & Style

Jared is direct, humorous, and compassionate, blending solidarity with listeners (“I know you. You were at my show. I have a connection to you.”, 39:12) with pragmatic, sometimes blunt wisdom (“Shut the fuck up, then don’t come here. This club is so depressing; get out of my club.”, 45:30). His approach is grounded in self-examination, personal responsibility, and the recognition that modern dating requires both clarity of purpose and resilience.

Summary

This Mailbag Monday episode distills dating truths, from understanding hot-and-cold partners to taking ownership of your dating goals, especially on the apps. Jared’s advice is crystal clear: know what you want, state it up front, and don’t waste time on those who demonstrate (intentionally or not) that they aren’t on the same page. His blend of real talk and encouragement makes the sometimes discouraging landscape of dating a bit more navigable—and a lot funnier.