The JTrain Podcast
Episode: Dating in Your 40s: Sad Single or Fun Single?!
Host: Jared Freid
Guest: Chris Lamberth
Date: March 4, 2026
Type: Chit Chat Wednesday
Episode Overview
In this lively episode, comedian Jared Freid welcomes returning guest and fellow comic Chris Lamberth for a Chit Chat Wednesday discussion centered on dating in your 40s—exploring what it means to be a "sad single" versus a "fun single." The conversation blends humor, candid reflections on relationships, personal growth, and the realities of dating, especially as men age. Chris also provides updates about his new relationship, his love for the arts, and his new comedy special, "Killing in Obscurity." The episode finishes with a spirited game where the hosts debate which solo activities tip into "fun" or "sad" territory for single guys in their 40s.
Key Discussion Points & Insights
Birthdays, New Relationships & Signs from Exes
- Mutual Birthdays: Both Jared and Chris recently celebrated their birthdays (Feb 21), joking about sharing the date with celebrities like Jennifer Love Hewitt and Kumail Nanjiani.
"Couple of February 21st guys in here, the worst day of the year." — Jared (01:42)
- Relationship Update: Chris shares he's been seeing someone for about seven months, marking a shift from his previous appearances on the show as a single man.
- Navigating Post-Breakup Dynamics: Chris details an amicable run-in with his ex, who came to his comedy special taping and texted a "great job" salute emoji.
“Great job. And she gave me the salute emoji. And I was like, oh, wow, she's there.” — Chris (03:40)
- Jared Analyzes Breakup Texts: Jared humorously overthinks the emoji and tone, suggesting anything short of full enthusiasm from an ex feels "passive aggressive."
"Anything in the middle from an ex to me is passive aggressive." — Jared (04:23)
The Joy (and Path) of Dating in Your 40s
- Meeting on Hinge, Letting the Night Unfold: Chris recounts meeting his girlfriend on Hinge and letting their first encounter evolve naturally from drinks to an impromptu pizza trip—demonstrating that there are no hard rules for "perfect" first dates.
“That shows that there’s no rules for a first date, right? You have fun and the only rule is: let it happen.” — Jared (15:13)
- Comfort in Compatibility: Chris expresses the sense of ease with his new partner and how the relationship feels organic and comforting—like “sitting in a nice couch.”
"You seem happy. You seem at ease. ... It kind of feels like you sat in a nice couch." — Jared (19:56)
- Mutual Interests: They discuss sharing interest in live events, plays, and concerts, and how joint adventure helps relationships grow.
The Arts: Plays, Music, and Cultural Adventures
- Theater as Self-Care & Cultural Immersion: Chris, a trained theater practitioner, describes the inspiration and energy from going to see Off-Broadway plays and live music, encouraging listeners to seek these experiences.
"Just as a fan, I love going just the same as I would going to a basketball game or football game." — Chris (07:06)
- How to Find Local Events: For fans wanting more culture, Chris recommends following local theaters, Googling upcoming seasons at playhouses, and being open to what’s playing nearby.
"You follow the different theaters. ... Google theaters near me and, like, the playhouse that’s near you. You can see what their season is." — Chris (09:58)
- Shared Joy in Discovery: The satisfaction of finding "rookie card" cultural experiences, paralleling supporting up-and-coming comedians or bands.
Reflections on Loneliness, Health, and Personal Growth
- Vulnerability and Health: A standout bit from Chris's special involves going to a colonoscopy appointment alone, and how witnessing others with supportive partners led him to reflect on his own life choices.
"It's very sobering when you think...Am I living my life right?...It’s sobering. And so I needed to ... step my game up." — Chris (23:41)
- Turning Real-Life Struggles into Comedy: Both comics discuss the art of translating personal pain and “awe” moments into relatable stand-up, referencing Marc Maron's philosophy that dark stories can be funny when you’ve processed them.
"When you do it the way we do it, you’re excavating things that probably made you feel bad in a moment...and trying to turn that into art..." — Chris (28:25)
Inside Chris Lamberth's Comedy Special: "Killing in Obscurity"
- Themes: Chris’s special weaves together stories of career wins, family pride, and the gritty day-to-day of artistic life.
"My favorite joke is the closer, the Spike Lee story...I wanted to capture on film, on record, about career, about the pursuit of a career." — Chris (25:25)
- Parental Pride: Chris movingly recalls his parents seeing him on the big screen and the unique validation that brings, as opposed to more ephemeral recognition via social media.
"Taking my parents to a movie that I was in with Melissa McCarthy...just a great moment in my life." — Chris (27:36)
GAME: Sad Single or Fun Single? (31:59)
Jared and Chris play a game inspired by Chris's colonoscopy bit, debating whether popular solo activities are empowering or a little sad when done as single men in their 40s.
Activities & Debates
- Rock Climbing (32:00)
- Verdict: Fun single. It's a cool, individual activity and not inherently lonely.
- Wine Tour (33:01)
- Verdict: Sad single. Wine tours feel more "couple-y" or for groups; solo can feel awkward.
"By the middle of it, they were like, what are you doing here?" — Jared (34:52)
- Verdict: Sad single. Wine tours feel more "couple-y" or for groups; solo can feel awkward.
- Bar Alone (36:11)
- Verdict: Borders on fun but quickly turns sad if you stay too long and no connections happen.
- Memorable moment: Jared likens being at a bar alone, flanked by office parties, to being the divider on a grocery store conveyor belt. (36:43)
- Reflecting (38:10)
- Verdict: Sad. The idea of "just reflect" as a fun activity reads more like a cry for help.
- Notable quote:
"If someone told me, ‘Jared, why don’t you go reflect today?’ I’d be like, do you hate me?" — Jared (38:21)
- Cooking Class (39:41)
- Verdict: Fun. Cooking is seen as aspirational and attractive; it’s social and self-improving.
"Cooking class is aspirational, too. Like, you’re learning to cook something for someone." — Jared (39:55)
- Verdict: Fun. Cooking is seen as aspirational and attractive; it’s social and self-improving.
- Video Games (41:03)
- Verdict: Fun. As long as there's balance, having a passion—even playing games—is engaging and shows you have interests.
"If it’s fun, you just gotta balance it out." — Chris (41:38)
- Broader reflection: Jared highlights that having any interest, no matter how niche, is almost always better than none—a recurring dating struggle.
Notable Quotes & Memorable Moments
-
On the Ex’s Salute Emoji:
"Anything in the middle from an ex to me is passive aggressive. You could have taken the L, but it’s not really an L."
— Jared (04:23) -
On Comfort in Relationships:
"It kind of feels like you sat in a nice couch."
— Jared (19:56) -
On Being Supportive at Life’s Big Moments:
"You see another guy there and his wife is picking him up after the colonoscopy...it’s sobering when you think about that."
— Chris (23:41) -
On Solo Wine Tours:
"By the middle of it, they were like, what are you doing here?"
— Jared (34:52) -
On Aging and Comedy:
"My dad asked me if I was happy...I said, ‘yeah, I’ve done everything that I wanted to do as a child. I’ve done it already. And it was because of you.’”
— Chris (25:25) -
On Reflecting Alone:
"If someone told me, ‘Jared, why don’t you go reflect today?’ I’d be like, do you hate me?"
— Jared (38:21)
Important Timestamps
- 00:00–02:10: Opening banter, birthdays, quick catch up
- 02:10–06:00: Chris’s relationship update; ex etiquette
- 06:00–11:00: The value of arts, live plays & supporting new acts
- 15:13: Lessons from letting first dates happen organically
- 19:56–21:38: Comfort & compatibility, adventures with partners
- 23:41–25:25: Reflections on alone-ness and parent pride
- 31:59–44:08: "Sad Single or Fun Single" game
- 44:08–end: Closing gratitude, plugs for Chris’s special
Final Thoughts & Takeaways
- Dating in your 40s is about authenticity and knowing what brings genuine joy, not arbitrary social rules. Chris and Jared agree that ease, compatibility, and an openness to experience—not grand gestures or ticking boxes—are what make relationships work.
- Solo experiences: fun or sad? It’s about intention, attitude, and context. Some activities empower singles, while others—like wineries or bars alone—can slide into melancholy. Cultural or learning experiences (cooking class, plays) are almost always seen as positive.
- Personal growth and self-awareness are essential at any age, but "reflecting" as an activity should maybe come second to action and real connection.
- Chris’s new special, "Killing in Obscurity," is not just funny but deeply personal. It explores the realities of chasing creative success, family pride, and the journey from feeling "sad single" to "fun single"—and maybe, to "happy partnered."
Listen to the full episode for more laughs, stories, and insights. Don’t forget to check out Chris Lamberth’s new special, "Killing in Obscurity," and follow him on social media (@ChrisLamberth) for more.