The JTrain Podcast - "Two Ex Husbands Later: Red Flags I Ignored in My Marriages!" Chit Chat Wednesday – February 25, 2026 Host: Jared Freid
Guest: Jackie Fabulous

Episode Overview

In this Chit Chat Wednesday edition of The JTrain Podcast, comedian Jared Freid sits down with the always-effervescent comedian, friend, and expert in being fabulous—Jackie Fabulous. The episode is a candid, heartfelt, and hilarious conversation about relationships, ignoring red flags, post-divorce reflections, and finding joy (and humor) in singlehood after two marriages. Jackie shares wisdom gleaned from her two ex-husbands, her “lover girl” tendencies, and why being single past 50 can be fabulous.

Key Discussion Points & Insights

1. Ignoring Red Flags in Marriage (01:05–06:35)

• Jackie’s Approach to Marriage Red Flags:

  • Jackie reveals she was self-aware during both of her marriages, sensing they may not last even at the start.
  • On her first marriage: “We did not consummate the marriage at that wedding night. And I knew that was a sign...” (02:47–03:03, Jackie)
  • She stayed because, after years together, “fuck it, we might as well do it,” but immediately felt regret after the ceremony.
  • Jared relates: “I’m someone who bails even when it’s going good because I know it’s not all there for me.” (03:24, Jared)

• Motivations for Staying and Leaving:

  • Jackie: “If you don’t feel like this person is making it lighter, then I don’t understand the point.” (05:26, Jackie)
  • The allure of wanting a relationship to work sometimes outweighs visible red flags—especially when swept up in the fantasy of “finally” being together.

2. Social Media, “Lover Girl” Tendencies, and Exes (10:57–12:22)

• On Sharing Relationships Publicly:

  • Jackie unapologetically shares her significant others on social media: “When I’m into it, I don’t give a...what’s love? It doesn’t matter...You’re just that person. Absolutely.” (11:09–11:39, Jackie)
  • Jared dubs her a “lover girl”—bold, affectionate, and unashamed in her love.

• The Downside of Attraction:

  • Physical attraction kept her in her second marriage: “How often do you get somebody who’s hot as fuck, you’ve known for decades that you can marry? That doesn’t happen.” (12:08–12:22, Jackie)
  • But ultimately, "as hot as he is, I am not having a good time." (12:15, Jackie)

3. Self-Discovery and Embracing Single Life (13:01–14:10)

• Jackie reflects on patterns: “I’ve always in some way or shape or form had a boyfriend...but there’s always somebody filling that space. And I realize now, at 54, I’d kind of want to just enjoy my life and not have to worry about if somebody else is hungry.” (12:24–13:01, Jackie)

Memorable Moment:

• Best Thing About Being Single:
  “I masturbated the other day and as soon as I was done, my first thought was, I am so glad nobody is here.” (13:05, Jackie)

• Jared adds, “That is the, the adult moment...when you masturbate to completion and you go, ah, the whole bed is mine.” (13:16, Jared)

• They joke about starting a vibrator company called Carefree Slumber. (13:54–14:04)

4. Dating & The Anxiety of Milestones (16:05–18:08)

• Jared on Dating in His 40s:
  “I get stressed out...since turning 40, for me it’s been a thought of like...if you really want to make this happen...” (16:07–17:03)

  • He acknowledges, for men, the timeline of marriage and kids hits later: “Women are doing that way earlier than men.”
  • “I don’t need it. I want it with the right person that it would be fun with.” (17:04, Jared)

• Jackie has been celibate for ten months, and finds it liberating: “When the itch comes, I’m like, okay, am I going to text...or can I just rub one out and be like, oh, thank God I didn’t text.” (17:46–18:08, Jackie)

5. Comedy Process, Writing, and Style (07:43–10:57, 19:04–24:15)

• On Jackie's Comedic Voice:

  • Jared praises Jackie’s “cadence:” “You have a cadence that I don’t think anyone else has...it actually feels like, you know how they talk about ASMR? You do like comedy ASMR.” (07:44–08:41, Jared)
  • Jackie shares her process—her tendency for “long-ass lists,” which come from turning crowd work and complaints into new jokes. (08:41–09:35, Jackie)

• Discussion on Material and Words on Stage:

  • Both comics discuss words they avoid or use on stage (e.g., Jackie avoids saying “pussy,” but is fine with “dick,” while Jared muses on using “cunt” as a punchline). (22:19–24:28)
  • On the power of “shock” in language: “Once they hear it, once the shock is gone, you’ve lost the ammo.” (24:15, Jared)

• Standout Joke:
  Jackie’s favorite joke she left out of her special:
  “When I walk in any Marshall’s, Trader Joe’s, or what have you, I have to ask myself, can I here...see this?” (20:47, Jackie describes this as a 40+ experience—can I poop here?)

6. Fab or Drab Game (30:25–41:05)

• The show closes with Jared’s "Fab or Drab" segment, rapid-fire opinions on everyday pleasures:

  • A warm morning coffee?
    Jackie: “I daydream at night about the cup I’m going to have when I wake up. So fabulous.” (30:48) Jared prefers a 4:00 PM coffee ritual. (31:13)

  • Loosening jeans after a big meal?
    Jackie: “Fab in public? Drab. At home? Fab.” (31:58) Jared: “To me, the fabulous thing at home is seeing the jeans that are on the floor as if I melted.” (32:01–32:26)

  • Rainbows and freshly fallen snow?
    Rainbows are fab, but snow in New York? “It keeps fucking snowing.” (34:01, Jackie)

  • Reconnecting with old friends?
    “Fabulous. I have been doing that...I unfortunately am the kind of person that when I do fall in love, I disappear. And that’s a character flaw...” (39:56, Jackie)

    • However, sometimes, “unless we were talking about a particular person or their own lives, she and I had nothing...it’s hard to hang out with a friend who really does not do well or is not happy.” (40:34, Jackie)

7. On Life, Family, and Finding Joy (33:35–39:26)

• Jackie and Jared swap stories about food, family, and moving:
  • Jackie reveals she’s from the Bronx, living in LA, and is inheriting her childhood home; Jared details his recent move to Delray Beach, Florida, and adapting to the idiosyncrasies of life among retirees.
  • “To live there, you have to change your temperament if you’re going to live amongst people.” (35:12, Jackie)
  • “You’re going to yell at this woman on her last days on earth?” (35:28, Jackie jokes about Jared’s impatience with older Floridians)

Notable Quotes & Memorable Moments

• On dangerous optimism in relationships: “You just wanted it to work so bad, I didn’t care what red flag he put in front of me.” (05:47, Jackie)
• The single life revelation: “I masturbated the other day and as soon as I was done, my first thought was, I am so glad nobody is here.” (13:05, Jackie)
• Comedy as catharsis: "It's my way of just turning crowd work and complaining about shit into a new joke. And audiences like the long ass list." (09:35, Jackie)

Timestamps for Key Segments

• Red Flags & Marriage Regrets: 02:47–06:35
• Social Media & Love: 10:57–12:22
• Best Part of Being Single: 13:01–14:10
• Dating Anxiety After 40: 16:05–18:08
• Comedy Voice and Lists: 07:43–10:36
• Material Writing & Word Choice: 19:04–24:28
• Fab or Drab Game: 30:25–41:05
• Reflections on Friendship: 39:56–42:47

Conclusion & Recommendations

The episode blends honest humor and real-life experience, offering listeners both laughter and validation—especially those navigating post-divorce life or singlehood in midlife. Jackie’s candor on attraction, loneliness, and self-worth is uplifting and relatable, while Jared provides his own unique perspective as a single comic entering his 40s.

Don't miss Jackie Fabulous’ special You Can Leave on Hulu.
For more funny, heartfelt conversations with comedians, tune in to Chit Chat Wednesday each week on The JTrain Podcast.