The JTrain Podcast – "Laughing Through the Red Flags" ft. Ian Lara – Chit Chat Wednesday

Date: December 10, 2025
Host: Jared Freid
Guest: Ian Lara
Episode Theme: Navigating Comedy, Dating, and Identity with Humor

Episode Overview

In this lively “Chit Chat Wednesday” episode, comedian and host Jared Freid welcomes friend and fellow comic Ian Lara—“an expert in being a Dominican daddy”—to the podcast. The main focus is a comedic deep-dive into modern dating, the realities of stand-up’s self-discovery, and the distinctiveness (and overlap) of cultural quirks, particularly among Dominicans. They also celebrate Ian's new YouTube special, Material Boy, unpacking everything from digital dependence to dating disasters, creative process, and cross-cultural hilarity.

Key Discussion Points and Insights

On Modern Digital Life and Moving

• Internet as the Cornerstone of Home
  • Jared discusses moving homes and equates a home’s starting point with its Wi-Fi installation.
    • “...the beginning of your new home is when the Internet is there.” (01:29)
  • Both reminisce about the shift from cable to internet as the new essential and reflect on the struggle to disconnect.
  • Notable Quote:
    • Jared: “We don't want to be around our own thoughts. Like, what do I even do here if I can't go on Instagram and look at people?” (02:21)
• Desire to Disconnect—But Not Really
  • Ian envies (in theory) old-school types like Ari Shaffir who use flip phones, but admits he could never do it.
  • Jared jokes about “living the piggish lifestyle that Wall-E promised us” and the many “life hacks” he’s tried (unsuccessfully) to limit phone time.
    • “I get off my phone every day for about 20 minutes while I'm in the shower, and that's, like, enough for me.” (03:52)

The Comedian’s Relationship with Their Phone

• Screen Time Confessions
  • As comedians with newly released specials, both obsessively check their phones for feedback:
    • Ian: “My screen time, bro, it's like, at 11 hours, dude.” (04:41)
    • Jared: “Mine's worse… being on the road… the only friend you got is the phone that connects you to other friends...” (04:48)
  • The phone becomes both company and validation machine during long stints of solo travel.

Dating and Relationships: Comedy vs. Real Life

• Comedy Material & Relationships

  • Jared and Ian discuss the dangers and dilemmas of relying on personal relationships for material—especially when life evolves faster than recorded bits reflect.
    • “...the hard part about being a comic is you put something out and you go, oh, well, that was taped at a part of my life that I was feeling those things and I was saying them that way. And now I've evolved, and I would say it differently now.” – Jared (07:59)
  • Ian notes many comedians struggle updating relationship-based material after a breakup; he leans toward exaggeration and character, not just pure truth.
    • “I’m kind of doing a character on stage. It’s an exaggerated character… I'm mocking myself and other people's stories.” (10:36)

• The Evolving Language of Jokes

  • Jared reflects on consciously shifting language in his act—moving from “men” and “women” to simply “I” for both accuracy and responsibility.
    • “...if I say men, it's just me absolving myself from the responsibility.” (08:44)

The Culture (and Challenge) of Dating as a Comic

• Dating App Fatigue

  • Ian has been off dating apps for over five years, finding them “too sex forward” (15:17) and almost transactional.
  • Jared jokes he never gets direct sexual messages; Ian suspects his approachability makes him a “safe option” for bold women.

• Comedian Appeal and Pitfalls

  • They explore why comedians are alluring dating prospects (“safe adventure,” validation of normalcy and excitement), but also why the need for constant validation is a turn-off once discovered.
    • “I want instant feedback... It’s the only art where we get to hear back right away.” – Jared (17:04)
  • Success in dating for comics is often tied to “killing” on the date—the feedback loop remains crucial.
    • “You ever been on a date where you feel like, man, I am killing. Kind of like you're on stage?” – Ian (18:10)

• The Power of a Laugh

  • Both agree that a great laugh from a date is a make-or-break factor:
    • Jared: “When women have great laughs, I am like, I'm in.” (18:45)
    • Ian: “Best part is, like, when she's talking and then I'm tagging her stuff, but it's killing, like, so I'm barely saying anything, but every time I speak, it's a laugh.” (19:37)

• Bad Pickup Lines & Being ‘Challenged’

  • They roast DMs that try to “neg” comedians (“you're not that funny”) as the least effective approach imaginable:
    • “Your opening line to me is going to be that I'm not funny...? That my whole life's work was a mistake?” – Jared (21:53)
  • They agree it's emotionally tone-deaf:
    • Ian: “We have dedicated our lives to get approval from people telling us we're funny... and your opening line... is that I'm not funny?” (21:36)
  • Both prefer compliments, even if it supposedly risks inflating egos:
    • Ian (sarcastically): “I don't want to make your head big or anything, but I think you're really funny. And I'm like, make my head big. I was suicidal. You just saved me.” (22:38)

Creativity & The Comedy Process

• Favorite Bit from the Special: The ‘Dead Cat’ Story

  • Ian recounts working for years on a story about being asked to remove a roommate’s dead cat during a post-date night—a “five-minute chunk” that finally hit just right.
    • “I spent like, no joke, like seven hours, like, pacing, walking around, trying to find the beats to the story... and immediately I was like, this is going to be one of my favorite bits.” (27:02)
  • Jared notes, as a guy dating post-35, there's often a “pet you have to act like you love” before you're attached to the person. (25:44–26:51)

• Workshopping Material & Growth

  • Both stress that bits (unlike social media content) are worked and reworked until they’re “done thousands of times.” (27:52)

Cultural Specificity: The “Do Me, Do Me Dominican” Game

(Jared quizzes Ian about uniquely Dominican habits for universal life events)

• Birthdays (29:16)
  • “Dominicans take birthdays very seriously… like you’re gonna die within the next 12 months. So we have to enjoy this one.” – Ian (29:21)
• Barbecues (30:32)
  • Start late (8–9pm), end early morning (4–5am) — not “daytime” events
• Moms (31:00)
  • Dominican and Jewish moms are “very similar”—overbearing, deeply in your business, competitive with the spouse.
• Dads (31:19)
  • “Not emotional, angry a lot for no reason... being happy is like a sign of weakness. So you gotta... always just be angry and stern and command respect.”
• Gifts (31:37)
  • Cologne is the classic Dominican gift for men; Ian owns 30+ bottles, now “institutionalized” to love it.
    • “I have some colognes that… to get the scent off you, you got to go through a car wash.” (32:41)

Notable Quotes & Memorable Moments

• On Dating as a Comic:
  • Jared: “When women have great laughs, I am like, I'm in.” (19:01)
  • Ian: “I think I got that [sex-forward messages] 'cause I just seem non-threatening. I think these girls thought, like, if it came down to it, I'll fight them… so they felt comfortable taking these risks with me.” (15:40)
• Creativity & Rewriting:
  • Jared: “...if I say men, it's just me absolving myself from the responsibility. I'm like, right, guys? Right. We all do this. Instead of, like, I do this, which makes it harder to say. But if I won't even say I do it, then I shouldn't be making a joke about it, you know?” (08:44)
• On Digital Addiction:
  • Ian: “My screen time, bro, it's like, at 11 hours, dude.” (04:41)

Timestamps for Key Segments

• 01:15 – Ian’s intro as “Dominican daddy,” talking about moving and internet as home
• 03:10 – The pitfalls of digital minimalism and flip phones
• 04:41 – Screen time confessions and the addictiveness of constant feedback
• 06:40 – Promoting Ian’s special and the importance of viewer support
• 07:38 – The struggles of using personal relationships as comedy fuel
• 10:36 – Ian on stage persona and “exaggerated character” vs. confessional stand-up
• 14:48 – Discussion of dating apps and Ian’s experience as a safe, “sex-forward” option
• 17:04 – Validation, comedy, and how feedback-seeking bleeds into dating
• 18:10 – Killing (or bombing) on dates parallels killing (or bombing) on stage
• 19:37 – Tagging a date’s remarks for laughs; power of a good audience (date)
• 21:00 – Riffing on “pickup negs” — why challenging a comic’s funniness is a losing strategy
• 25:09 – Ian’s “dead cat story” and the intricacies of crafting long-form material
• 28:23 – “Do Me, Do Me Dominican”: Dominican birthdays, barbecues, parental quirks, gift-giving

Conclusion

This episode blends sharp comedic banter, personal insight, and cross-cultural perspective as Jared and Ian riff about everything from the grind of modern dating to the mechanics of a killer stand-up bit. For comedians, their fans, or anyone grappling with digital addiction and authenticity, it’s a funny, warm, and self-aware listen—and a loving plug for Ian Lara’s new special, Material Boy (YouTube).

For more:

• Watch Ian’s latest special, Material Boy ([YouTube link in episode description]).
• Follow @IanLara on social for more jokes and cultural insights.
• Tune in every Wednesday for more “Chit Chat” with Jared Freid and guests!