The JTrain Podcast: "Why Does Raya Suck? - MONDAY MAILBAG"

Host: Jared Freid
Date: April 13, 2026
Format: Listener Mailbag – Jared reads audience emails and offers advice, focusing on dating, relationships, and life dilemmas with his trademark honesty and humor.

Episode Overview

This Monday Mailbag episode features Jared Freid reading and dissecting listener emails about messy breakups, friendships after faith transitions, and the frustrations of exclusive dating apps like Raya. With his signature comedic flair and candid insights, Jared navigates complexities of modern relationships, post-divorce dating, and dating app culture. This particular episode is light on guests, maximizing Jared's direct, no-nonsense style as he processes real stories with empathy, practical advice, and unforgettable one-liners.

Key Discussion Points & Insights

1. Email #1 – Dating a Divorcing Cafe Owner with Baggage

(Starts ~03:30)

Context

• Listener, 31, meets a 43-year-old cafe owner in spring 2024.
• He was married, had three kids, messy public breakup after wife cheated.
• They reconnect in 2025, begin dating; she's clear she wants marriage and kids.
• He seems committed, then in early 2026 starts pulling away, saying he's overwhelmed with life.
• Eventually goes quiet, ignoring her requests for closure and to retrieve her belongings.

Jared’s Analysis & Advice

On telling others how they feel:

“You are basically telling him how he feels… Can’t tell you how to feel is rule one now.” [07:00]

• Jared points out the listener is projecting by assuming he's "still healing" – it's more honest to say what you want and don’t want.

On dating someone with heavy baggage:

“Cafe owner with three kids. Let's have some more. And he's 43 already. I mean... You hit, and then reality.” [12:40]

• He emphasizes the severity of taking on someone with three kids and a messy breakup and illustrates the overwhelming reality.

On mixed signals and ambiguous closure:

“Happy birthday. That keeps the ball in the air, keeps you as an option... Get my stuff back has finality to it.” [18:35]

• Jared deciphers why the man wishes to keep the door ajar for emotional convenience but runs at any sign of finality.

On text exchanges post-breakup:

“He is trying to not get in trouble... He likes his world... Shaking you up is adding another hole that he's not sure he can handle.” [28:00]

• Dissects the professional, detached tone of their texts, pointing out neither is being truly honest or human with the other.

Clear Advice:

“You need a breakup. I think getting together... I wanted my stuff so I could have one last talk with you, where I wanted acknowledgment.” [38:40]

• Jared prescribes a real breakup text, being direct and human, to allow both to truly move forward.

2. Email #2 – Being the “Tour Guide” for a Friend Leaving Mormonism

(Starts ~40:30)

Context

• Listener, early 40s, has a lifelong friend recently left Mormonism.
• The friend, formerly "sheltered," now wants help trying new things (coffee, tattoos, swearing, vibrators).
• Listener feels conflicted: proud, but frustrated by friend's naivety and the time investment needed.

Jared’s Analysis & Empathy

On feeling used and friend boundaries:

“You knew each other at 18... but I would feel a little used. But you’re doing a nice thing...” [43:25]

• Jared acknowledges the delicate balance between being generous and feeling like an unpaid life coach.

On channeling frustration:

“How are you so stunted? Yet she got married early. She has four kids. She was in the church... That was not in her worldview. So how isn’t the question.” [46:00]

• His key insight: What seems obvious to one may be totally foreign and intimidating to another because of upbringing.

On setting limits:

“I need them to understand that they’re taking up my time... I’m not just here as your tutor.” [50:18]

• Suggests honest conversations about availability—support her, but maintain your own boundaries.

Practical Advice:

• Welcome her to the "mainland," but be honest about how much energy you can give.
• Don’t be condescending; lead with empathy, and only take on as much as you want.

3. Email #3 – “Why Does Raya Suck?”

(Starts ~56:55)

Context

• Listener complains about Raya, the “exclusive” dating app – frustrated, can't seem to quit, feels underwhelmed by actual outcomes.

Jared’s Signature Analogy & Insight

“I would compare Raya to a nightclub... There’s a bouncer outside... you go in and everyone is standing against the wall, not dancing while looking at each other.” [57:50]

• Jared likens Raya to a club where everyone wants entrance, but no one does anything – sure, you’re in, but nothing happens.

“It’s a lot of people browsing, not buying.” [58:45]

• It’s less a dating app, more a trophy for being attractive or cool enough to be let in.

“You can’t leave because, like all dating apps, it’s what might happen next... the next like might be your next husband or a magical romance.” [59:25]

• The “FOMO” keeps people glued to it, especially with the prospect of matching with celebrities.

“On Raya, the pictures are better... It’s as if everyone got a professional photoshoot. Even if their job doesn't necessitate a headshot.” [1:00:25]

• Everyone’s profile is curated to Instagram-perfection, seldom showing real vulnerability.

“Vulnerability produces vulnerability. Raya lacks vulnerability, so it lacks dates.” [1:01:10]

• Without written profiles and substance, real connections are scarce—Jared’s neat thesis for why Raya "sucks".

Notable Quotes & Memorable Moments

• On ambiguous breakup texts:
  “Happy birthday. That keeps the ball in the air... Get my stuff back has finality to it.” [18:35]

• On projecting feelings onto others:
  “You’re basically telling him how he feels... Can’t tell you how to feel is rule one.” [07:00]

• On life after divorce with kids:
  “He’s holding all of those ropes. He's putting his hand in all the holes that have the water coming into the ship... Shaking you up is adding another hole.” [28:00]

• On Raya’s unique brand of disappointment:
  “Raya is a nightclub where everyone wants to get in and nobody dances.” [57:50]

• On setting friendship boundaries:
  “I need them to understand that they’re taking up my time... I’m not just here as your tutor.” [50:18]

• On vulnerability (or lack thereof) in dating apps:
  “Vulnerability produces vulnerability. Raya lacks vulnerability, so it lacks dates.” [1:01:10]

Segments & Timestamps

• 0:00–03:30 – Show intro, mailbag setup, call for emails
• 03:30–39:00 – Email 1: The messy breakup with a divorced cafe owner
• 40:30–55:00 – Email 2: Supporting a friend through newfound independence after leaving Mormonism
• 56:55–1:02:00 – Email 3: “Why Does Raya Suck?” and Jared’s definitive answer

Episode Tone & Style

Jared Freid’s trademark blend of raw honesty, playful analogies, and empathetic candor shines—he tells listeners the hard truths ("You can't tell someone how they feel"), but matches it with warmth (“Welcome to the mainland, but be honest about what you can give.”). His comedic timing and real-life observations make both the tough and light-hearted moments memorable, encapsulating what makes the JTrain Podcast a must-listen for advice seekers and comedy fans alike.

For more advice (or a send-up of the modern dating scene), send your questions to jtrainpodcast@gmail.com, and catch every new episode on Monday.