Man of the Year – Champions of Friendship

Episode #149: Poker Nights

Aired September 16, 2025

Hosts: Matt Ritter & Aaron Karo

Episode Overview

In this lively episode, Matt and Aaron dive deep into the ins and outs of "Poker Nights" as a staple for friendship among men, especially dads. The conversation explores the logistics, pitfalls, and rewarding aspects of hosting and participating in poker and game nights, with plenty of humor, personal anecdotes, and practical advice. The hosts also answer a listener's dilemma about a poker night that's losing its friendly vibe. The tone is candid, irreverent, and relatable—perfect for anyone interested in nurturing adult friendships.

Key Discussion Points & Insights

1. The “Truly Tasteless” Joke Book Poker Night

• Matt's Poker Night Recap:
  • Matt describes hosting a poker night inspired by the “Truly Tasteless Joke Book” (02:57), highlighting the boundaries of “acceptable” tasteless humor and the wild card when someone goes fully “off book” (03:25).
  • Matt: “Somebody went off script and just went, I’m just gonna tell my own joke... I’m glad we weren’t recording that.” [03:18]
• Setting the Scene:
  • The event was a gathering of dads (with one non-dad), focused less on hardcore gambling and more on camaraderie: “Nine dads and Dana.” [06:46]
  • Taco Bell was a late-night staple: “It was like six burritos wrapped inside another burrito.” (06:09)

2. Planning and Logistics of Poker Night

• First-Time Struggles:
  • Matt admits to being a rookie at organizing, fumbling with chips and the buy-in, and texting friends for guidance: “I know this is obviously not that hard, but it was like, oh, I had to figure all that stuff out.” [07:21]
  • Opted for a $40 buy-in with a rebuy option, keeping the stakes reasonable.
• Dealer Dilemma:
  • Debate over hiring a professional (and possibly topless) dealer: “She offered up topless for double.” [09:05]
  • Rejected the idea—“It’s gross and distracting... I’ll pay you extra to keep your top on.” [09:48]
  • Settled on keeping things in the group and “letting loose a little bit.” [10:03]

3. Poker as a Social Vehicle

• Inclusivity and Vibes:
  • Aaron notes he wasn’t invited because he doesn’t enjoy or know how to play—“I would never. Thank you, Dan. And thank you, Matt.” [06:59]
  • Matt explains the event wasn’t about poker prowess but giving dads space to relax: “Everybody there needed that [night to let loose].” [10:21]
• Skill vs. Socializing:
  • In any group, there are serious players and those just there for fun, which sometimes causes tension:
    • “The guys who play regularly got really annoyed... half of us just want to schmooze and hang out.” [10:39]
  • Matt set expectations early: “Nobody’s that good... this is gonna be low stakes.” [11:02]

4. Tangents and Traditions: Cigar and Bourbon Culture

• Cigars:
  • Hosts riff on the ritual of cigar smoking at poker nights and its questionable appeal:
    • “Can we just admit that it’s gross?” — Aaron [11:59]
    • “I can’t fathom ever getting into it, but a lot of guys are into it.” — Matt [12:05]
  • Matt shares practical advice: “I don’t like cigars because I don’t like imposing externalities on others.” [13:11]
• Drinks:
  • The evening featured quality bourbon (Hibiki, Angels Envy, Michters), served with large ice cubes: “Only had eight... didn’t have enough for everybody.” [14:54]

5. Depth vs. Fun: What Should a Game Night Be?

• Serious Sharing vs. Blowing Off Steam:
  • Matt reflects on resisting his usual urge for a “circle of trust” or deep conversation:
    • “Sometimes you just need fun... as adults, we’re not blowing off enough steam. Am I wrong?” [16:24–16:46]
  • The night focused on casual enjoyment, validating the need for pure relaxation among friends—especially dads.

6. Listener Mail: Saving a Fractured Poker Night

Question: A listener writes in because their poker night has become too competitive, with tension and arguments overshadowing friendship.

• Hosts’ Advice:
  • Communication is key; set group expectations about stakes and seriousness.
  • Matt: “It’s hard if everybody’s not aligned on what it is.” [25:51]
  • Aaron: “It falls on the host to do a little bit of curation.” [28:07]
  • Possible solutions: Reset the vibe, consider a different game, split into separate groups ("serious" and "casual"), or have some rounds light, some rounds serious.
  • “People shouldn’t be coming to blows at your freaking poker night... or any night.” — Aaron [31:56]

7. Game Night Alternatives

• Other Games Ranked:
  • The hosts debate the merits of Monopoly, Trivial Pursuit, Pictionary, and Scrabble.
  • Final rankings:
    • Aaron: “Trivial Pursuit, Pictionary, Scrabble, Monopoly.” [34:12]
    • Matt: “Pictionary, Scrabble, Trivial Pursuit, Monopoly.” [34:18]

Notable Quotes and Memorable Moments

• On Tasteless Jokes:
  • "For some reason, they were always crapping on Helen Keller. NASA had its own section. The Challenger had just happened." — Matt [03:35]
• On Poker Night Food Choices:
  • "It was like six burritos wrapped inside another burrito. And I had the whole thing." — Matt [06:09]
• On Host Boundaries:
  • "I made everybody stay outside. I didn’t give them access to the house... With my little kids, yeah. So that was my rule." — Matt [20:56]
• On Group Dynamics:
  • "That's the nature of groups, isn't it? ... You're just not going to have equal enthusiasm for everything you're doing together." — Matt [27:14]
• On Resisting Forced Depth:
  • “I did a really good check in of, like, what’s happening here. And what I noticed was just people really enjoying themselves. And I was like, just let that ride.” — Matt [15:43]
• On Game Night Reset:
  • “You just got to communicate with the guys. No fighting at poker night. Come on, guys.” — Aaron [33:11]
• On Blowing Off Steam:
  • “As adults, we're not blowing off enough steam. Am I wrong?” — Matt [16:33]
• On Adult Friendships:
  • “I think you need a little bit of a reset... people shouldn't be coming to blows at your freaking poker night.” — Aaron [31:56]

Timestamps for Important Segments

• 02:57 – Poker night setup & "Truly Tasteless" joke book story
• 06:09 – Taco Bell confession & poker food traditions
• 09:05 – The topless dealer discussion (and why they said no)
• 10:39 – Group divides: Serious players vs. hangers-on
• 11:02 – Setting expectations for casual poker night
• 15:19 – Did the group have “deep” moments or just fun?
• 16:33 – “We’re not blowing off enough steam” discussion
• 20:56 – Enforcing house rules and keeping kids safe
• 24:22 – Listener asks for help saving a fractured poker night
• 25:51 – Group alignment issues and restoring friendship-first culture
• 28:39 – Alternative games: Parcheesi, backgammon, and more
• 34:12 – Debating and ranking classic board games
• 35:10 – How often poker night will happen in future

Summary

This episode of Man of the Year is a comedic and honest reflection on what makes game nights—especially poker—for grown-up friendships so rewarding, challenging, and sometimes messy. Matt shares a behind-the-scenes look at organizing his first “dad poker night,” complete with late-night Taco Bell, hesitation over hiring a professional dealer, bourbon, and the challenges of balancing competitive and casual attitudes.

The hosts emphasize the importance of communication and “setting the tone” to ensure the night remains about relaxing and forging (and maintaining) friendships—not about who takes home the most chips. They remind listeners not to force depth where it doesn’t fit; sometimes, just having “fun for fun’s sake” is essential for adults who have limited time away from family and work obligations.

For those facing similar group challenges, Matt and Aaron offer actionable strategies: clarify expectations, reset as needed, don’t be afraid to switch up the game, and always prioritize the spirit of togetherness. This blend of warmth, humor, and practical insight makes the episode both entertaining and genuinely useful for anyone invested in adult friendships.

To share your own poker/game night stories or friendship dilemmas, reach out to Man of the Year on Instagram or at manoftheyearpodcast.com.

“Be good to yourself. Be good to your friends. Love you, buddy.” — Man of the Year sign-off [35:36]