The JTrain Podcast – "How Do I Get a Guy to Ask Me Questions on a Date?! - MONDAY MAILBAG"

Host: Jared Freid
Date: February 23, 2026

Episode Overview

In this Monday Mailbag episode, comedian Jared Freid tackles listener emails about modern dating frustrations and relationship dynamics. Solo from his chair in Delray Beach, Jared provides honest, humorous, and practical advice, drawing on years of giving crowd-sourced dating guidance. This episode features three in-depth listener questions covering icks in dating, emotional curiosity (or the lack thereof) in men on dates, and the etiquette around awkward in-law dynamics—all explored with Jared’s trademark blend of empathy, candor, and wit.

Key Discussion Points & Insights

1. Defining the "Ick" and How to Trust Your Feelings

[06:15–33:24]

• Email 1: A 37-year-old woman writes in about her “ick” after two dates with a 43-year-old man met on Hinge. Her turn-offs: his Instagram algorithm full of scantily clad women, multiple dating apps on his phone, and his eagerness to move things forward.
• Jared breaks down the concept of the ick:
  • The ick is your own feeling—not something that requires justification or group validation.
  • It’s different from a universal turn-off (like dirty nails or being rude). “One woman's husband is another woman's ick.” (09:40)
• On seeing “sexy women” on a guy’s Instagram:
  • Jared defends the male gaze with comedic transparency:

    “You also wouldn’t want to fuck me because my Instagram ‘for you’ page is big old titties. It’s big old titty place. That’s where my scroll slows down.” (13:37)

• Multiple dating apps ≠ he’ll take anyone:
  • Jared suggests that the “ick” often comes from not being that into someone to begin with.
  • “I think when you start getting into the nitty gritty of like, ‘he has three dating apps, so that must mean...’ I think you were looking for reasons to be right about ending it with a guy who was just nice enough.” (25:04)
• The myth of ‘feeling special’ on dating apps:
  • Jared sympathizes with the desire to feel chosen but notes the transactional casino nature of modern dating:

    “Yeah, that's the problem with the dating apps. They don't feel special. They are quite literally playing a numbers game.” (22:18)

2. Getting Men to Show Emotional Curiosity

[36:34–57:12]

• Email 2: A listener asks if it’s a red flag that after saying her day was “bad, chaotic, and weird,” her date doesn’t follow up, just moves on.
• Jared’s take:
  • Possible explanation: Many men are simply “checking the box” of asking questions because they've heard they should—without real engagement.

    “He may have only heard ‘men don’t ask questions on dates.’ That's what he heard. And he's like, I gotta check this box.” (41:17)

  • If a guy consistently doesn’t follow up or show depth, it’s probably not fixable—especially by the third date.
• How to handle it:
  • Jared suggests playfully calling it out:

    “Hey, I just told you my day was bad. Do you want to hear about it, or were you just wondering if I had a good or bad day?” (49:05)

  • Real change is unlikely; if you notice this and care, it may be a sign to move on.

3. In-law Etiquette: When Your Mother-in-law Calls You “Mama”

[59:05–1:18:00]

• Email 3: A new mom vents about her mother-in-law’s intrusive “mama” nickname and overstaying her welcome after the baby’s birth.
• Jared’s prescription:
  • Address through your husband—he’s best equipped to deliver the message kindly and be part of the solution:

    “The line of communication [from] daughter-in-law to mother-in-law is rocky at best. So I’m bringing him in.” (1:12:12)

  • If you must, express it directly but with humor: “Hey, when you call me ‘mama,’ you make me feel like I’m a cow getting chugged on, on their titties.” (1:15:52)
  • A playful revenge tactic: Give her an awkward grandma nickname she dislikes in return.
• Broader insight:
  • Generational and algorithmic echo chambers mean older in-laws might be unaware of how cringey or memed such behaviors are:

    “She’s not on the TikTok algorithm with a guy wearing a towel… She hasn’t seen this lampoon.” (1:06:50)

Notable Quotes & Memorable Moments

• On the ick:

  “You’re allowed to feel that way. I’m telling you, none of this screams more than just a guy to me… But icks aren’t meant to be fair.” (18:39)

• On dating app realities:

  “Don’t tell me how the hot dog is made. This is how the hot dog is made.” (21:02)

• On men and asking questions:

  “He may have only heard 'men don't ask questions on dates.' That's what he heard. And he's like, I gotta check this box.” (41:18)

• On mother-in-law etiquette:

  “No one calls a mama ‘mama’ because they're purposely trying to irritate them. They call them ‘mama’ because they think it's fun.” (1:14:07)

Important Timestamps

• 00:06–06:12 – Introduction, show structure, tour plugs (skip to 06:13 for first email)
• 06:13–33:24 – The “ick,” male Instagram behavior, feeling un-special on apps
• 36:34–57:12 – Lack of emotional curiosity from men on dates, is it a red flag?
• 59:05–1:18:00 – Surviving the mother-in-law, pet-name etiquette, generational cringe

Tone & Style

Jared’s responses are candid, warm, self-aware, and punchy—often blending serious advice with irreverent humor. He empathizes with listeners’ dilemmas, admits his biases, and makes space for both their feelings and the annoying realities of modern romance.

Summary Takeaways

• Trust your own ick—it’s personal and doesn’t need group approval.
• Signs of disengaged or emotionally uncurious dates are rarely flipped by prompting; look for vibes not checklists.
• When handling awkward in-law habits, use your partner as a liaison and pick your battles with humor and boundaries.

For questions or to submit your own dilemma: jtrainpodcast@gmail.com