Son of a Boy Dad #361: No Cigars for Office Men

Podcast: Son of a Boy Dad
Host: Barstool Sports
Date: December 18, 2025

Episode Overview

In this end-of-year episode, Lil Sasquatch confronts his recent step into the world as a college dropout, while producer Rone and co-host Harry join him for a playful, rambling, and often self-deprecating look at manhood, holiday traditions, and life’s little absurdities. As their last in-person recording of 2025, the trio reflect on rituals, office politics, and the hilarity of everyday struggles—from forbidden office cigars to who does the heavy lifting on family trips and the mysteries of Christmas lights.

Key Discussion Points & Insights

1. Holiday Office Chaos & Cigar Capers

• The episode opens with Harry bringing swag from a gamer friend (controller gifts), sparking banter over who introduced whom, gifting etiquette, and perceived slights in friendship.
• Roan tries to introduce cigars into the recording as a celebratory gesture for the last in-office show of the year, but this leads to a discussion about office rules and resistance (06:00).
• Memorable Moment: The gang debates the limits of office mischief and whether it’s worth angering staff just for the “vibe”:

  “Nothing makes me happier than a cigar. I don't want to upset the company.” – Roan (11:32)

2. White Elephant Gift Exchanges & Internal Company Dynamics

• Roan laments Harry’s non-participation in the office White Elephant gift exchange, which segues into sarcastic commentary on company culture and who really holds power at Barstool.
• “That's always been the truth of it, is that we need the booking people. The booking people don't need us.” – Roan (14:07)

3. Manhood and the Burden of Carrying Luggage

• The hosts riff on expectations for men, especially husbands, to “lug all the heavy stuff” during family trips—a relatable theme that becomes a running joke about masculinity, hot girl dimensions, and the humility of not being the “strong man” at home (16:00 – 19:30).
• “Dude, that's a hot girl. Those are like hot girl dimensions.” – Sass (18:08)
• “When everyone. Whenever I'm bringing in. I'm taking everything in one trip. No matter what.” – Harry (19:39)

4. Christmas Traditions, Family, and Seasonal Nostalgia

• The conversation goes deep into each host’s holiday routine, from Christmas Eve family gatherings to the fatigue induced by syrupy waffles and cinnamon rolls (72:12 – 85:40).
• Quotable:

  “Eating syrupy waffles more than taking Ambien.” – Sass (85:36)

• Harry describes familial denial of Santa’s non-existence, revealing layers of family tradition and gentle ribbing (78:11).

5. Travel, Nature, and Childhood Memories

• The hosts reminisce about summer trips, owning land on Lake Ontario, and arduous journeys from Maine to Canada, painting vivid pictures of tradition, discomfort, and adventure (32:31–34:58).
• Quotable:

  “Our camp was called Windmill because we had an old abandoned windmill on the island. It was great.” – Sass (32:46)

6. Great Lakes, Exotic Gifts, and the Value of Old Stuff

• Half-serious, half-absurd conversation about submerged champagne, expensive cigars, and the notion of value—stories about shipwreck wine, hand-rolled cigars, and the comparison to art or rare collectibles (27:13–31:28).
• “You just have a house or like 20 minutes of pleasure.” – Roan on expensive cigars (27:48)

7. Gender Norms & Christmas Decorations

• Spirited debate about white vs. colorful Christmas lights, with Harry defending his love for bright, chaotic displays against Roan's “white lights are classy” argument (49:26–52:28).
• “Colorful lights is kinda poor.” – Roan (50:53)
• “I'm with Harry on this one... White lights. It's a girl move. I hate to be that guy.” – Harry (50:29)

8. Olympic Events, Athletes & the Absurdity of Tradition

• Long, humorous riff on which Olympic events deserve to stay or go, why the hammer throw exists, and the surprise that long jump with a pogo stick is worse than without (55:01–57:11).
• “That just crossed all the lines.” – Harry after Sass mistreats his controller (24:09)

9. Travel & Loneliness: Christmas Abroad

• Sass plans for an upcoming solo trip to New Zealand over Christmas, expressing both excitement and anxiety about spending the holidays alone—and a public plea for Kiwi listeners to offer companionship or golf partners (39:55–42:51).
• “If there's any cunts down in New Zealand that would take in Francis...” – Roan (41:39)
• “I'm gonna call my family at, like, in a tent. 11pm on Christmas Day. And they will just be getting up to unwrap presents.” – Sass (41:52)

10. Random Oddities & Urban Life

• The group marvels at weird city phenomena: piles of used condoms at the dump, seeing safe-sex precautions on subway steps, and the mystery of why Moynihan Train Hall is so much cleaner than Penn Station (64:11–68:41).
• “It occurred to me, who had sex on these steps and had not only had sex on these steps, but had protected sex?” – Sass (66:17)

11. Gift Giving & Consumerism

• Discussion on the pressure and awkwardness of asking for Christmas gifts as adults, and how Amazon’s convenience has “killed Christmas” for those who once delighted in surprise (79:14–83:34).
• “Amazon, Loki, has killed Christmas.” – Roan (83:22)

Notable Quotes & Memorable Moments

• [06:00] Roan: “It's our last episode in person of the year.”
• [18:08] Sass: “Dude, that's a hot girl. Those are like hot girl dimensions.”
• [50:53] Roan: “Colorful lights is kinda poor.”
• [72:25] Harry: “Of course I'm going to honor my family by waking up... We used to wake up at like 6am and honestly, that probably went on a little longer than I would like to admit.”
• [85:36] Sass (on Christmas fatigue): “Eating syrupy waffles more than taking Ambien.”
• [41:39] Roan (on Christmas abroad): “If there's any cunts down in New Zealand that would take in Francis...”

Timestamps for Key Segments

• [06:00] – Cigar caper and office friction
• [14:07] – Company politics & the White Elephant exchange
• [16:00–19:30] – Stereotypes about men and holiday lifting/luggage
• [32:31–34:58] – Childhood camp stories, Lake Ontario
• [49:26–52:28] – White vs. colorful Christmas lights debate
• [55:01–57:11] – Olympic events and pogo sticks
• [64:11–68:41] – NYC oddities: condom piles, safe sex on subway stairs
• [72:12–85:40] – Family Christmas traditions, food, and gift etiquette

Tone & Style

The conversation is informal, fast-moving, and densely packed with banter, inside jokes, and self-mockery. The trio are irreverent but warm, quick to poke fun at themselves and each other, but always returning to real, relatable anxieties about adulthood, tradition, and friendship.

Summary

“No Cigars for Office Men” is quintessential Son of a Boy Dad: equal parts nostalgia, social observation, and playful chaos, with hilarious detours into office politics, masculinity, family rituals, and the awkwardness of growing up. While celebrating a year of shows, the hosts lean into the discomfort, joy, and absurdity of what it means to be an adult at the holidays—and whether you can ever really learn “how to be a man” by torching a stogie at 11AM in your place of work.

End of Summary