The JTrain Podcast — "Do I Shoot My Shot With My Optometrist?!? - MONDAY MAILBAG"

Host: Jared Freid
Date: December 29, 2025

Episode Overview

In this “Mailbag Monday” edition, Jared Freid answers listener emails on dating dilemmas, vulnerability, and relationship boundaries. Broadcasting solo from Delray Beach, Florida in the final days of 2025, Jared not only addresses the main question—should you shoot your shot with your cute optometrist?—but also weighs in on navigating intimacy timelines and reflects on a listener’s journey to saying “I love you” after divorce. Delivering insight, humor, and a signature dose of empathy, Jared’s tone ranges from playful to sincere as he guides listeners through their tangled love lives.

Key Discussion Points & Insights

1. The Optometrist Crush — How to Shoot Your Shot

[07:00 - 22:30]

• Listener Question:
  A 37-year-old woman wonders if she should try connecting with her attractive new optometrist after feeling a potential “vibe” during her exam. She asks if it’s weird to message him on LinkedIn, since she can’t find his Instagram.

• Jared’s Advice:

  • Owning Your Perspective:
    Jared dramatizes how framing your own story can shape outcomes and attraction, reading the email aloud in two wildly different tones—a self-deprecating and a confident, positive one:

    “See the difference? Do we see how much I want to hang out with one person? I changed a few words... just made one a little sadder, one a little sexier.” (11:45)

  • Embrace Curiosity:
    He shares that “curiosity” is his new mantra for 2026, encouraging the listener to find out what might happen—without crossing boundaries.

    "Let’s go back to my 2026 mantra—curiosity. Find out what it means to me: C-U-R-I-O-S-I-T-Y. You will find a hot guy.” (15:10)

  • How To Approach:
    Jared suggests being direct, positive, and light—giving the optometrist every opportunity to say yes (or no) without awkwardness or pressure:

    “I’d go to LinkedIn. I’d say, ‘Hey, I really enjoyed our conversation the other day. I don’t want to cross any patient–doctor boundaries ... but would love to get a drink sometime if you’re up for it. Here’s my number… If this is totally not something you do with patients, I’ll totally understand.’” (18:20)

  • Don’t Do Half-Shots:
    Jared warns against the wishy-washy “half-shot”—you have to be clear and confident in your intentions.

    "I'll never get back to a half-shot. I'll never take interest in a half-shot. It will always scream danger to me." (16:59)

• Tone & Encouragement:
  Jared uses a “dancing on the line” metaphor: come to the “dance floor” ready for a good time, make your interest known, and allow people an easy way to decline without discomfort.

2. Physical Boundaries and ‘Fifth Date’ Fallout

[24:55 - 33:35]

• Listener Question (via Instagram DM):
  A woman asks why a man didn’t text the day after she declined to go further physically on their fifth date. Is he just after sex, or did his ego get bruised? Should she reach out?

• Jared’s Analysis & Advice:

  • Honesty Is a Win:
    Both people are being forthright about their needs—she’s drawing a boundary, and he’s choosing to opt out rather than give false hope.

    "You turned him down… That is a win. You have told someone what you wanted. You were honest." (27:02)

  • Not About Ego:
    Jared rejects the ego-bruised narrative:

    "I've gotten turned down. And I don't go, 'Oh, oh, how will I ever look at another woman in the eye again?'" (29:20)

  • When Paths Diverge:
    Jared explains that the decision not to keep communicating is often about a mismatch in intentions, not a simple “he just wanted one thing” scenario.

    "He goes back... and goes: Do I want that level of intimacy with this person? And do I want to lie to someone? He chose masturbation and I think there's something to be commended..." (30:40)

  • Should You Text?:
    If he wanted to pursue something, Jared reasons, he would have. There’s no need to chase closure—let the silence be the answer.

3. Follow-Up: “Saying I Love You Again After Divorce”

[33:40 - 40:10]

• Listener Background:
  A year prior, a listener wrote about nerves in saying "I love you" to her new boyfriend, her first serious relationship since divorce.

• The Update:
  She did tell him, he didn’t say it immediately, but did a few weeks later. Now a year and a half in, the relationship is “going so well, I could die.”

  “Getting up for work is a slog, especially in the dark winter mornings, and your show makes it easier... I listen as I get dressed ... it’s the best way to start the day with a smile.” ([Listener email], ~35:00)

• Jared’s Emotional Response:
  Jared openly shares how much these kinds of follow-ups mean to him:

  “I’m, like, getting emotional reading that. I’m trying to hold back from crying a little bit. This is so beautiful and nice ... what an amazing, beautiful thing to connect with people all around the world in this way.” (37:15)

• Reflections on Podcasting:
  He speaks candidly about the unexpectedly meaningful feedback from listeners over the years and the pleasure of helping—originally just wanting to make people laugh, but now cherishing the genuine connections.

Notable Quotes & Memorable Moments

• On Positive Framing:

  “If you stay happy, you’ll find happiness. If you be negative, you’ll find negative… It sounds stupid as I say it, but of course you do.” (12:30)

• On Making a Move:

  “Don’t half-shoot a shot… Come in positive. Hey, I really enjoyed talking to you the other day. Would love to get a drink sometime. I’m free next week. Here's my number. Make a plan and I'm in. Done.” (18:30)

• On Intimacy Boundaries:

  "That is communicating. That is saying what you want… That's a win for everybody. We all kind of—we all showed who we were in that moment." (26:55)

• On Audience Connection:

  “Being there in these odd moments that you’re by yourself… That is—what an added bonus. What an amazing, beautiful thing to connect with people all around the world in this way.” (37:30)

Timestamps for Important Segments

• Mailbag Monday Explanation & Podcast Format – 00:00–06:30
• Optometrist Crush Letter & Advice – 07:00–22:30
• Half-Shot Dating Philosophy – 15:30–19:00
• Sponsor Discussion (Rocket Money) – 22:35–24:20 (advertisement skipped)
• Fifth Date Boundaries Q&A – 24:55–33:35
• ‘I Love You’ Follow-Up & Reflections – 33:40–40:10

Overall Tone

Jared’s style is friendly, energetic, playful, and candid—quick to poke fun at himself and others, deeply empathetic, occasionally poignant. He balances humor with practical advice, always returning to the importance of self-respect, clarity, and vulnerability in dating and life.

Takeaways

• Positively frame your circumstances and intentions—it affects outcomes.
• When shooting your shot (even at the optometrist), be direct, positive, clear, and offer an easy out.
• Communicating physical or emotional boundaries is a win, no matter the result.
• Vulnerability—like saying “I love you” again—pays off, even if it requires patience.
• Listener feedback genuinely impacts Jared, and he cherishes the podcast’s sense of community.

To write in for advice:
Email jtrainpodcast@gmail.com or DM @jtrainpodcast (follow first to have your message considered).