The JTrain Podcast – Mailbag Monday: "Do I Keep Dating A Really Nice Guy?"

Host: Jared Freid
Date: January 12, 2026

Episode Overview

In this episode of the JTrain Podcast, Jared Freid tackles a fresh batch of listener emails on the classic Mailbag Monday. Recorded from Delray Beach, Florida, Jared answers questions about whether to continue dating "really nice" people who just aren't a match, explores the "ick" factor in dating, discusses navigating awkward breakups, and gives insight on self-respect and honesty in relationships. Judgement-free advice, relatable stories, and a healthy dose of humor come together to create a supportive sounding board for all things love and modern dating.

Key Discussion Points & Insights

1. Dating Someone Who Is "Pretty Good" – Is That Enough?

• Listener’s Dilemma: After six dates with a "pretty good" guy, the listener is on the fence. Several cringe moments (awkward sex, behavior at a friend's party, going Dutch on tickets and food) left her uncertain if she’s being too picky or just not that into him.
• Jared’s Take: If your best review of someone after six dates is “pretty good,” you probably have your answer. "Is that the life you want to live? If this got 10% better, would it change everything?" (04:11)
• Insight: Sexual compatibility and small annoyances (“the ick”) aren't necessarily dealbreakers if the connection is amazing. But when there’s no spark, even minor irritations are magnified. If you’re still stuck thinking about a shared hot dog after six dates, it’s a no.
• Notable Quote:

  “To me, if someone—if my best friend came up to me and said, 'I went on six dates with this guy, overall pretty good,' I would go, is that the life you want to live?”
  - Jared Freid, (04:11)

Important Segment:

• Discussing the role of age and settled lifestyles when making dating decisions
  • 00:00–06:00

2. The "Ick" Factor – Should You Trust It?

• Listener Example: The "Red Bull bunny rabbit" encounter and the latke-fetching incident at a Hanukkah party. These cringey moments snowballed into an avalanche of ick.
• Jared’s Take: Sometimes the ick is just a mask for incompatibility. The details are less important than the vibe—you’re allowed to move on without a lengthy justification. Don’t worry about being too picky if the connection isn’t there; the “ick” is a valid reason.
• Notable Quote:

  “This is about the match, not you versus them.”
  - Jared Freid, (04:25)

• Humorous Highlight:
  Jared's act-out of the latke situation, poking fun at requests that just feel emasculating or awkward in public.
  • 06:40–08:10

Important Segment:

• Breakdown of “the ick” and how to handle it
  • 06:00–09:00

3. Splitting Costs and Low-Effort Dating

• Example: The guy asks if $60 for a hockey ticket is okay, then offers to buy her ticket if she Venmos him, and later suggests she use the water fountain rather than buying her a water.
• Jared’s Take: While financial communication is good, the vibe matters—you want the other person to make it feel like a date, not a transaction.
• Notable Quote:

  “If they’re asking you if the amount’s okay, you are paying.”
  - Jared Freid, (08:20)

4. How to End Things Kindly and Quickly

• Listener Asks: Was I too picky for breaking it off? Should I have explained why, or just listened to “the ick” and moved on?
• Jared’s Reassurance: Ending it is enough. No need for a blow-by-blow breakdown. Sometimes it’s better to “fail faster,” move on, and learn to spot what you want more quickly.
• Notable Quote:

  "If you’re still thinking about the hot dog, then it wasn’t extraordinary enough to distract you from the hot dog. There it is. Not too picky. Good luck.”
  - Jared Freid, (12:02)

5. Dating the “Sweetest, Kindest” Person — A Red Flag?

• Listener Dilemma: After a hard divorce, she rushed into dating the “sweetest, kindest man,” but now realizes the chemistry isn’t there and is dreading hurting him.
• Jared’s Take: “Sweetest, kindest” is often code for “not exciting enough.” Don’t go on a trip you already know you’re not emotionally invested in. Dragging things out doesn’t soften the hurt—it just confuses and delays healing.
• Advice: Be honest, don’t try to “boost his spirits” by pretending, and don’t treat breakup candidates as fragile.
• Notable Quote:

  “Nobody’s spirits are boosted by the person who’s going to dump them.”
  - Jared Freid, (19:55)

• Actionable Insight:
  "You need to say, 'I've had a really great time with you… but I am not in this relationship for the long haul.'"
  • 23:20

Important Segment:

• Walking listeners through how to break things off pre-trip
  • 18:50–23:30

6. Sudden Breakups and Confusing Closure

• Listener Story: After five years together, a couple has a phone argument, takes a break, and the boyfriend announces a new girlfriend within days—without clearly ending the previous relationship. Now there are angry texts and public confusion.

• Jared’s Insight: This is messy and more about miscommunication (and perhaps mental health struggles), but the key is focusing on your own healing, not his narrative.

• Memorable Quotes:

  “You’re so caught up with how you look that you don’t really care about how you feel.”
  - Jared Freid, (30:43)

  “Let’s fail quicker. This relationship was a failure. You are not a failure.”
  - Jared Freid, (33:20)

Important Segment:

• Reading the screenshots and walking through actionable closure and boundaries
  • 24:23–33:30

Notable Quotes & Memorable Moments

• “If you make 10% on your money, you’ve had a great year. Do you think it’s gonna get 25? If we put this in numbers, it gets less personal and it makes the decision easier.”
  - Jared Freid, (04:45)

• “The minute you go into, ‘Am I being too picky?’... If everything was amazing and you really loved this guy and you go, ‘But he bought a hot dog and said we could share it,’ I would go, yeah, you’re being too picky. But that’s not what this is.”
  - Jared Freid, (11:25)

• “Maybe this whole thing is a lesson for you to be a little bit more you when you’re dating.”
  - Jared Freid, (13:21)

• “Stop talking to someone like they’re a child. You need to say, 'Hey, I’ve had a really great time with you. This trip we have coming up, it’s just not going to happen for me. I am not in this relationship for the long haul.'”
  - Jared Freid, (23:20)

Episode Timestamps for Key Segments

• Opening & Explaining the Mailbag Concept: 00:00–03:00
• First Email ("Pretty Good" Guy Dilemma): 03:12–13:21
• Breakdown of the Ick Factor & Red Flags: 06:00–10:52
• Splitting Costs and Awkward Dates: 08:20–10:52
• Ending Things Kindly – Listener Email: 12:05–14:52
• Sponsor/Ad (Skipped)
• Second Email ("Sweetest, Kindest Man" and the Breakup Trip): 18:17–23:20
• Breakups, Closure, and the Dangers of Focusing on Their Narrative: 24:21–33:20
• Final Thoughts on Healing & Moving On: 33:21–end

Summary & Final Advice

Jared consistently encourages honesty—for yourself and with others—and not to linger in relationships that lack excitement, connection, or authenticity, no matter how “nice” or “sweet” the other person might be. He underscores the importance of listening to your gut (the “ick”), failing fast, not worrying about seeming “picky,” and putting your feelings before outside narratives or concerns with how things look. The episode wraps up with a reminder: relationships are about the match, not the résumé, and self-respect is always the right decision.

To submit your dilemma:
Email jtrainpodcast@gmail.com or DM @jtrainpodcast on Instagram.