Podcast Summary: “Spending the Holidays Alone Can Be Special”

Podcast: All Of It (WNYC)
Host: Alison Stewart
Guest: Josh Gondelman, Comedian
Air Date: December 29, 2025

Overview

This episode of All Of It explores the nuanced experience of spending the holidays alone. Host Alison Stewart, alongside comedian Josh Gondelman, examine why the season can feel isolating, how aloneness is distinct from loneliness, and how listeners can find meaning, comfort, and even joy in solo holiday celebrations. The episode builds community live on air through listener calls and messages, offering both practical advice and uplifting “pep talks” to foster connection.

Key Discussion Points & Insights

1. Cultural Expectations and Holiday Loneliness

• Opening thoughts on solo holidays:
  • The holidays are loaded with images of togetherness, making solitude feel strange or even negative.
  • “There’s such cultural weight, right, on the holidays … all these indelible images of families celebrating and traditions that often require a number of people.” — Josh Gondelman (02:44)
• Social media influences:
  • Seeing others’ celebrations online can intensify feelings of being “left out.”

2. Aloneness vs. Loneliness

• Understanding the difference:
  • Solitude can be meaningful, creative, and empowering rather than inherently lonely.
  • “Just because you were by yourself doesn’t mean it has to be a bad feeling.” — Josh Gondelman (03:43)
• Personal anecdotes:
  • Alison and Josh share how spending time alone—whether as a creative staycation or a hotel night down the block—can refresh and re-center.
  • “I had this period of alone time. I could write, I could think about what the show is gonna be. I could think about what I wanted for the world.” — Alison Stewart (04:29)

3. When Community Becomes Essential

• Recognizing when alone turns to lonely:
  • It’s important to notice when solitude stops feeling positive and starts feeling isolating—especially during major holidays.
  • “When something isn’t going well and you’d like comfort and support and love… that’s when you turn to community.” — Josh (05:28)
• Diagnosing loneliness:
  • Recognition is a key motivator to seek reconnection:
    • “It definitely helps to fix a problem when you can diagnose it … the first step is knowing that not having that [community] is making you feel bad.” — Josh (06:18)

4. Coping with Social Comparisons and Expectations

• Pressure surrounding the holidays:
  • Discrepancy between expectation and reality can heighten loneliness.
  • “When expectations are set externally, it makes it double hard.” — Josh (09:07)
• Advice:
  • Focus on what matters to you—what would be truly meaningful—rather than what “should” happen.

5. Being Present While Alone or in Company

• Connection is not guaranteed by circumstances:
  • It's possible to feel lonely even in a crowd.
  • Tactic: Set the tone for the interaction you want, and initiate.
    • “If I wish more people were asking me questions... you can just talk to someone else. There’s no law against it.” — Josh (10:00)
• Mirroring desired behavior:
  • Jump into activities or conversations instead of waiting on others.

6. Listener Contributions and Strategies for Meaningful Solo Holidays

a. Community and Connection Stories

• Text from Kat, Mount Tabor, NJ:
  • Small towns and online community groups can offer local events, acts of service, and a sense of family—even if one lives alone. (11:33)

b. Coping with Loss During Holidays

• Advice for grieving families:
  • Allow room for both solitude and gathering; tailor holiday traditions to what feels comfortable.
  • “You don’t have to opt all in or out … check in with each other and be there for each other instead of just dragging someone along.” — Josh (13:22)

c. Filling Your Time with Meaningful Activities

• Call from Shimmy (Rockland County):
  • Emphasizes the importance of distinguishing between “alone” and “lonely," advocating for hobbies and joining groups (choir, congregation) to maintain connection. (14:02)

d. Finding New Traditions in the Unexpected

• Call from Caroline (Brooklyn):
  • Created a new tradition after a canceled flight: solo roast chicken dinner, baking, a quiet walk around the city. These routines became cherished, even when not solo. (22:21)
  • “On Christmas Day... in Brooklyn, it’s quiet and peaceful. It’s amazing just to walk around and enjoy the peace and quiet.”

e. Volunteering and Giving Back

• Call from Fidel (Jersey City):
  • Suggests reframing loneliness by doing something for others—making cookies for neighbors, volunteering, or simply engaging with the city’s energy. (19:14)
  • Josh echoes: Jewish Christmas (Chinese food, movies) and “invented rituals” like Whiskey Basketball Day can add fun and structure to solo holidays. (21:00)

f. Self-Care as Hibernation

• Call from Maggie (Sleepy Hollow):
  • Treating solo holidays as “self-care hibernation”—nature walks, new hobbies, and small creative projects.
  • “It’s a moment to hit pause and reboot a little bit.” (25:46)
• Text:
  • Museums, botanical gardens, or favorite places are sometimes better alone—allowing for a more direct, personalized experience. (26:55)

Notable Quotes & Moments

• On Solitude:
  • “Solitude can be joyful if you fill it with meaning.” — Josh Gondelman (03:27)
• On Social Comparisons:
  • “I have a really wonderful life that I'm doing the things that I want to be doing. And when I want to engage with my community in that way... we can have a party for any reason.” — Josh (09:07)
• On Starting New Traditions:
  • “You can create meaning in whatever venue is meaningful to you, even when it starts as a little tongue in cheek, but really helps build that community.” — Josh (21:00)
• On Helping Others Who Are Lonely:
  • “It is always a balance between making sure you're not giving so much that you're depleted yourself. But your care is really meaningful and special.” — Josh (31:01)
• Listener Praise:
  • “Can Josh come back every week? His positive outlook is needed therapy!” — Listener text (27:42)

Timestamps for Key Segments

| Time | Segment | |----------|------------------------------------------------------| | 00:07 | Alison introduces the episode and Josh Gondelman | | 02:44 | Why solo holidays can feel isolating—cultural weight | | 03:27 | Difference between loneliness and aloneness | | 06:18 | Recognizing and naming loneliness as a motivator | | 09:07 | Dealing with social comparisons and expectations | | 10:00 | Pep talk for feeling disconnected in a group | | 13:22 | Advice for grieving families on adjusting traditions | | 14:02 | Shimmy on hobbies and community as antidote to lonely | | 19:14 | Fidel on giving back as a tool against isolation | | 21:00 | “Whiskey Basketball Day” and building new traditions | | 22:21 | Caroline’s solo Christmas traditions | | 23:57 | Pep talk after a breakup during the holidays | | 25:46 | Maggie on self-care hibernation and new hobbies | | 27:42 | Listener calls for Josh’s upbeat energy regularly | | 31:01 | Pep talk for caregivers and first responders |

Tone & Feel

Warm, supportive, and gently humorous, the conversation is rich with empathy and encouragement. Josh Gondelman’s signature optimism shines:
“All you can do is all you can do. The intent of saving the world is so important.” (08:26)
Practical advice is seamlessly blended with personal stories. Listener contributions deepen the communal atmosphere, making the hour feel like the on-air “holiday party” Alison promised.

Takeaways

• Being alone during the holidays is not inherently negative; it can be empowering and rejuvenating.
• Recognizing true loneliness is the first step toward seeking connection or reimagining traditions.
• Engaging with small communities, giving back, or developing solo rituals can transform isolation into meaningful experiences.
• Both solitude and togetherness have their place—honor what you need, and support others while also caring for yourself.

Memorable Pep Talk
“This pain isn’t going to be forever. You do have other people in your community and your life who would love to help make your holiday more cozy.” — Josh Gondelman (23:57)

To anyone spending the holidays alone: You are not alone. Sharing, connecting, and even small gestures—toward yourself or others—can make this season bright in its own unique way.