The Find Out Podcast

Episode: "Golden Bachelorette’s Jordan Heller on Why Men Struggle to Make Friends After Divorce"

Released: October 28, 2025

Episode Overview

This episode of The Find Out Podcast diverges from the usual political fare to shine a light on the male experience: friendship, trauma, and loneliness, particularly following divorce and later in life. The hosts welcome Jordan Heller, fourth-place contestant from the first season of Golden Bachelorette. Through candid, often humorous, and deeply honest conversation, the group explores why men often struggle to make genuine friends after divorce, the cultural forces at play (including modern masculinity and political divides), and what reality TV unexpectedly taught them about real connection.

Key Discussion Points & Insights

1. Jordan's Backstory and Golden Bachelorette Experience

[03:29–08:52]

• Personal Background: Grew up in Skokie, Jewish, youngest of four boys. Divorced in 2015 after a long marriage.
• Entry on Golden Bachelorette: Daughters secretly entered him into the contestant pool in 2020. Had no idea until contacted by producers four years later, thought it was a scam at first.
• Show Process:
  • Was totally cut off from the outside world—no phone, TV, music, or books.
  • First met fellow contestants and the bachelorette, Joan, only on the initial night.
  • The show’s structure forced intense focus and emotional openness.
• Notable Quote:
  • "They take your phone, and then you're stuck... There's some things they don’t tell you about that experience...no one ever explained that to me." —Jordan [06:19]

2. Men, Vulnerability, and Forced Camaraderie

[09:26–16:10]

• Initial Competition Turns to Brotherhood:
  • The group quickly transitions from rivals to supportive friends.
  • "Pretty early on...it became about the guys pretty quick." —Jordan [13:19]
• Emotional Openness:
  • Contestants, mostly divorced or widowed, opened up about trauma more than they ever had, even with lifelong friends.
  • "I said things to those guys that I’ve never even said to my closest friends in life...there were genuine breakthroughs." —Jordan [15:00]
• Men Crying on TV:
  • The environment became like “60-year-old camp therapy.”
  • "It was so right early on and...I’ve never seen guys cry in general...but this was different." —Jordan [15:32]
• Comparison to Other Life-Altering Experiences:
  • Hosts compare the experience to basic training or starting university as an adult: being out of one’s comfort zone forges new, deep bonds.

3. Why Men Struggle to Make Friends After Divorce

[26:40–30:39]

• Isolation Post-Divorce:
  • After his divorce, Jordan felt embarrassed and kept to himself, didn’t share struggles even with his brothers or friends.
  • "I hid most of it...it was A, embarrassing and B, I just felt—you feel a little bit like a loser when that happens to you." —Jordan [26:43]
• Moving to the City for Anonymity:
  • Became anonymous in Chicago, which was freeing but also highlighted the difficulty of making new friends as a middle-aged man.
  • "That was a struggle...you kind of mingle through these divorce guy associates...your only thing in common is your divorce." —Jordan [29:36]
• Difficulty of Male Friendship:
  • “It’s very difficult to find guys who I’d like to hang out with in my mindset in my age group.” —Jordan [30:39]

4. The Loneliness Epidemic and Radicalization Risk

[30:50–36:20]

• Broader Context:
  • Hosts note a “loneliness epidemic,” worsened by COVID and remote work, and stress how isolation feeds into radicalization, especially for men.
  • "When men get isolated... it is far more...easy to red pill them, right, and to send them down a very dark and dangerous path." —Host [31:06]
• Right-Wing Media’s Echo Chamber:
  • The rise of “bro podcasters” and red-pill influencers fills the companionship void, pushing reactionary narratives.
  • Social media algorithms exacerbate the problem, reinforcing ideological silos.
• Need for Left-Wing Community Building:
  • The left lacks equivalents to the Tim Pools and Ben Shapiros, and needs to build more inclusive communities for men.

5. Gatekeeping, Grace, and Progressive Community Challenges

[38:02–42:56]

• The Problem of Gatekeeping:
  • Left-wing spaces often shut out people over old ideas or mainstream interests (like sports), unlike the right’s “no shame” embrace of members.
  • "We have circles...where if you walked in and you said, ‘Did you see the Bears get annihilated,’ they would go, ‘What the fuck are you talking about? Get out!’" —Host [37:56]
  • “We have to let people be normal again...it’s one person who’s the gatekeeper...and those are people we have to address.” —Host [38:02]
• Stories of Exclusion:
  • Jordan shares a story about his daughter facing ostracism in her LGBTQ+ friend group due to political disagreement, highlighting how purity culture and "cancellation" harms community.
  • "She’s not carrying around a flag, she just happens to be Jewish...the fact that they know and they’re trying to gang up on her..." —Jordan [38:37]
• Plea for More Grace and Nuance:
  • "You should be able to have a conversation about the war in Gaza...and disagree...but not cancel each other so you don’t have conversations." —Host [41:04]
• Inclusivity Is Essential:
  • "We need to be inclusive, if we want to win...we need to make those bridges." —Jordan [40:42]

6. Chicago’s Realities vs. Political Myth

[44:04–47:26]

• Media Myths Debunked:
  • Contrary to right-wing “hellscape” narratives, Chicago is vibrant, safe, and beloved by residents.
  • “Chicago gets such a bad rap...I live right on the lake, downtown Chicago ... Chicago is just incredible.” —Jordan [02:10]
• Political Showmanship:
  • Trump-era ICE raids in Chicago and other cities are described as performative stunts, not solutions.
  • "Marching up and down Michigan Ave...it's just show of muscle to intimidate people." —Jordan [44:38]
• Local Pride:
  • Despite challenges, Chicago keeps winning "Best Big City in America" and is a source of pride for Jordan and many residents.

7. Lasting Impact of the Show & Moving Forward

[48:37–54:55]

• Building Lasting Relationships:
  • The friendships forged on the show are real and ongoing—group trips and regular meetups among contestants.
  • “To a man, every guy would say the friendships are...real...we see each other.” —Jordan [17:59]
• Life After the Show:
  • Jordan has a new girlfriend, kids are thriving, and he’s continuing sports and community life in Chicago.
  • "Would I do another show? Not a dating one, now that I have someone, but another type of show could be fun." —Jordan [48:49]
• Recognition and Celebrity:
  • Adjusting to occasional fame from reality TV has mostly been positive.
  • "It's not enough that it's bothersome...people have really been nice...it's fun, and it opens some doors." —Jordan [50:11]

Notable Quotes & Memorable Moments

• On Emotional Vulnerability (Men Crying and Bonding)

  • “I’ve never seen guys cry in general…I have daughters, I cry, you know, Mulan, I’ll cry. But this was different. So these were guys who were talking about something they had probably never talked about… certainly not with a group of men.” —Jordan, [15:33]

• On Post-Divorce Isolation

  • "I hid most of it. I did not have even my brothers I didn’t. Maybe I gave them a little bit. It was A, embarrassing and B, I just felt…you feel a little bit like a loser when that happens to you." —Jordan, [26:43]

• On Building Community on the Left

  • "There’s no equivalent to half of these guys in the…right blogosphere, the Tim Pools or the, you know, Ben Shapiros…there just aren’t that many [on the Left]." —Jordan, [33:30]

• On the Political Weaponization of Loneliness

  • "When men get isolated…especially later in life, it’s a lot easier to essentially red pill them…and I think we have to solve this problem for people." —Host, [31:06]

• On Gatekeeping and Purity Culture

  • "We have to let people be normal again…we gotta deal with the gatekeepers…" —Host, [38:04]

• On Experiencing and Spreading Real Connection

  • "Somehow we can…if we can replicate it to the many, many men who could use something like this…you have to, again, remove everything…It certainly can be done." —Jordan, [25:03]

Timestamps for Key Segments

• [03:29–08:52] — Jordan’s personal background and audition process for Golden Bachelorette
• [13:19–16:10] — Men’s friendships, vulnerability, and “camp therapy” atmosphere on the show
• [26:40–30:39] — Post-divorce isolation, moving to Chicago, and struggle to find new connections
• [30:50–36:20] — Loneliness epidemic, risks of online radicalization, and the left’s failures in community building
• [38:02–42:56] — Gatekeeping in progressive spaces, purity culture, and a plea for inclusive grace
• [44:38–47:26] — Chicago as political symbol, ICE raids, and local pride
• [48:37–50:59] — Jordan’s current life, impact of reality TV fame, final reflections

Theme and Tone

The conversation is frank, heartfelt, and often irreverently funny, staying true to the podcast’s ethos of "no echo chambers, no bullshit." The hosts and Jordan commiserate over the real challenges of modern masculinity, isolation, political tribalism, and the transformative, unexpected power of vulnerability and real friendship. While the backdrop is the absurdity of America during Trump’s second term, the central through-line is a deep, leftist empathy—a call for more spaces where men can "be real" and build meaningful lives together.

Conclusion

This episode of The Find Out Podcast is a powerful exploration of modern male loneliness, the joy and challenge of forging new friendships after life upheaval, and how even a reality TV competition can be a catalyst for something deeply real. Jordan Heller’s story illustrates that given the chance (and sometimes when pushed out of their comfort zones), men—especially those in midlife—can form authentic, supportive bonds that are both healing and political in their resistance to isolation and radicalization. The hosts and guest leave listeners challenged to build, welcome, and nurture similar communities in their own lives.