Good Guys Podcast

Episode: Dating at 40 & Other Olympic Sports with Jared Freid

Date: January 26, 2026

Hosts: Josh Peck & Ben Soffer

Guest: Jared Freid

Episode Overview

In this lively and candid episode, actor/writer Josh Peck and entrepreneur/social media star Ben Soffer sit down with comedian, podcaster, and author Jared Freid. The trio dive into hilarious and insightful conversations about family, sports fandom, male friendships, and, most centrally, the realities of dating at 40. Personal anecdotes, plenty of self-deprecation, and sharp social commentary abound, making this episode both funny and warmly relatable.

Key Topics & Discussion Points

1. Family Dynamics & The Chicago Bears Game Experience

• Jared Recaps a Bears Game Visit
  • Jared shares his recent trip to a Chicago Bears playoff game, where his brother is part of the coaching staff.
  • Observations about being "the slapstick idiot brother" contrasted with his high-achieving sibling.
    • “I’m just there… spilling my drink on myself at the game and they’re like, Jared, two left hands, you know...” — Jared (01:57)
  • Discussion about sports as a family bonding experience, and the unique stress when a loved one’s job is on the line.
• Missing Out on Social Media
  • Jared jokes about his Instagram stories being muted during the game and how nobody noticed:
    • “No one even cared about what the fuck I was saying.” — Jared (03:47)
• Chicago Institutions & Rituals
  • The crew reminisce on Chicago classics, particularly legendary steakhouse Gibson’s and its iconic vibe.
    • “You walk into Gibson’s, it’s like walking into Chicago, Dan Aykroyd land… you go, I am in a snow globe that says Chicago.” — Jared (07:04)

2. Sports Fandom & Identity

• Personal Connections to Football
  • Josh reveals his father-in-law is Ken O’Brien, former Jets quarterback, leading to a reflection on sports legacy and how individual achievement is remembered (or overlooked) in team histories.
    • “You know, being a Jets fan ain’t easy, but Ken O’Brien made it a little easier.” — Security Guard, as relayed by Josh (13:06)
• Fandom as Community
  • The nuances of New York sports fans, and how allegiance can be a “character flaw” if it doesn’t fit expected patterns.
    • “If you tell me you’re a Brooklyn Nets fan… miss me.” — Ben (14:40)
  • Nostalgia for sports’ ability to unite cities and serve as a community balm.

3. Passion in Dating & Relationships

• Is Sports Fandom Important in Dating?
  • Jared reveals he loves when someone is passionate, whatever the subject:
    • “I just love when people love stuff… my knowledge? Yeah, just like you’re into something. If you’re into a team… bring me in, make me Uba Sop, tell me your fable.” — Jared (18:03)
  • Josh and Ben add that humor, personality, and realness are their green flags.
• Food & Eating Together
  • Conversation about eating preferences as relationship litmus tests, with Josh noting how his wife’s journey to veganism changed how they bonded over food.
• Passion vs. Performance
  • Jared discusses how dating app profiles often present a curated version of self, emphasizing the distinction between telling and showing:
    • “A lot of people are out there on apps being like, I am this and I do this, and then … you find out they’re like, you’re not an extrovert, you’re not an introvert… It’s a lot of telling before showing.” — Jared (20:57)

4. Dating at 40: Real Talk

• Friendships and Social Change Over Time
  • Jared contemplates the rarity of making new friends as an adult:
    • “Maybe Ben, like, we could get to know each other… you’re probably my first new friend in, like, two decades.” — Jared (36:42)
  • Observations on how men, unlike women, rarely actively seek new friendships.
• The Unique Dynamics of Dating in Your 40s
  • At 40, dating is qualitatively different—people have lived, accumulated stories, and "something has happened" to bring them to this point:
    • “The first date, to me, is all about figuring out what got us here. I think there’s intimacy in that — tell me the story that made it so you’re 35, 36, and a young woman who… you go, what’s the story?” — Jared (40:04)
  • Jared adds that if someone can’t articulate why they are single at 35-40, “they’re not ready.”
• Age-Gap Dating & Social Perceptions
  • The group lightly riffs on hypotheticals:
    • “If some hot 50 year old was like, Do you want to go out? I’d be like, Lydia, yeah, let’s go out.” — Josh (40:42)
• Men’s Reluctance to Make New Friends
  • Reflecting on their fathers’ social circles and the phenomenon of “renaissance” friendships later in life.

5. Society, Hating, and Hot Takes

• Judgment For the Sake of Contrarianism
  • The hosts and guest critique those who take negative stances on universally beloved things (e.g., Taylor Swift, hummus) just to seem interesting.
    • “I don’t like when someone hates things that the national population has decided on…” — Jared (27:39)
    • “Taylor Swift is ketchup. People in mass, people love ketchup.” — Jared (27:58)
  • Memorable Chuckle-worthy Moment: “No one hates hummus!” — (28:58)
• The Man in the Arena
  • The Roosevelt quote about “the man in the arena” gets referenced to highlight how easy it is to criticize when you aren’t the one putting yourself out there.
    • “It’s much harder to be the guy standing there performing… than to be up in the rows of crowds throwing shit.” — Josh (32:52)

6. Male Friendship, Couple Friends & Social Acceptance

• The challenge of making and maintaining couple friends, with both partners needing to “date” both halves of another couple (34:58).
• The unique emotional minefields in men’s friendships and how rare the formation of new ones becomes over time.

7. Airline Loyalty & Adult Pet Peeves ("What are you nuts?") [57:04]

• Airline Loyalty as Modern Madness

  • Jared shares a Delta Airlines gripe: Frequent flyer status means little when you end up in “comfort plus” instead of first, even with 2 million miles.
    • “My most committed relationship is to my airline.” — Jared (57:35)
    • “He didn’t get first class.” — Jared (61:04)

• Griping as Social Bonding

  • The team unpack their own small irritations and the satisfaction in bonding over mutual gripes, from Delta’s lackluster loyalty rewards to the idiocy of weather-based vacation planning.

Notable Quotes & Memorable Moments

• “If a Jew came up with [the Bears’ slogan], it’d be ‘grin and bear it.’” — Josh (01:16)
• “If I saw a guy play basketball with jeans, I would immediately hate him.” — Jared (09:27)
• “If you tell me you’re a Brooklyn Nets fan… miss me.” — Ben (14:40)
• “I like any passion. I just love when people love stuff.” — Jared (18:03)
• “You want a good improv partner. Dates are not stand-up.” — Jared (23:01)
• “I don’t even think I’m funny.” — Jared (23:47)
• “I call it FTG mode… when someone brings up a name, your initial response: fuck that guy.” — Jared (34:07)
• “Friendship is very rare as an adult… you’re probably my first new friend in two decades.” — Jared (36:42)
• “The first date is about, what got us here? Tell me that story.” — Jared (40:04)
• “My most committed relationship is to my airline.” — Jared (57:35)

Important Timestamps

• 00:26 – Show kicks off; introductions and riffing
• 01:00 to 05:00 – Jared’s Bears game story & family dynamics
• 07:04 – Chicago’s Gibson’s Steakhouse experience
• 10:25 – Discussion on sports fandom community and city pride
• 13:06 – Ken O'Brien Jets memories and sports legacy
• 17:41 – Transition to dating & relationship talk
• 21:22 to 25:00 – Passion, green flags, and dating as a public figure
• 34:07 – “FTG mode” and male social gripes
• 36:42 – Making new friends as adults; musings on loneliness
• 40:00 – Deep dive into what dating at 40 is really like
• 57:04 – “What are you nuts?” segment: airline loyalties and minor life annoyances

Final Notes & Plugs

• Jared Freid’s Book: “Walking Red Flag,” available for pre-order.
• Live Shows: Upcoming tour dates in NYC, Toronto, Boston, LA, and more (55:12)
• Podcast: The JTrain Podcast, daily episodes (56:09)
• Socials: @jaredfreid on Instagram & TikTok (“wizard of Ha”)

Tone & Style

True to the Good Guys brand: rapid-fire, self-deprecating, Jewish humor with a warm, open-hearted vibe. Conversation is personal, welcoming, and accessible—perfect for fans and newcomers alike. Expect a blend of banter, genuine reflection, and laugh-out-loud one-liners throughout.

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