Enjoy laughing about life's lessons through the eyes (and voices) of two loving people on their second marriage, over 50 (shhhh... don't tell) and second chance to screw things up for everyone. Cowboy and Kiki crave new experiences and share as they go.
We are a blended family with so much to share with you!
Scam tequila reviews, Rescue-dog fencing math, and marital translation services
If you've ever wondered what love, life, and questionable liquor purchases look like when narrated by two quick-witted co-hosts who cannot stay on one topic to save their lives—this episode is your sign.
Kiki and Cowboy stumble into recording because Cowboy "needs a recorded conversation to happen," quickly detour into the great Winner Winner Chicken Dinner mystery, and promptly spiral into a tale of scam tequila that turned out to be delicious, addictive… and probably just alcoholic sugar water they bought in Mexico.
Between dramatic V8-and-vodka confessions, parenting two dogs who both think they're only children, and auditioning new four-legged family members who could literally escape between fence slats, the episode is packed with:
self-roasting,
marriage-coded translation errors,
and more side quests than a Tolkien novel.
And just when you think the conversation finally lands on the new puppy—they remind you they still haven't actually introduced the topic they meant to discuss.
5 Humor-Loaded Highlights
They buy "tequila" in Mexico that turns out to be sugar water with vibes—but it's still the best thing they've ever tasted.
Cowboy proudly announces the episode is happening because he begged for attention—Kiki pretends to be surprised.
Kiki confesses she socializes the new puppy by putting him in tiny sweaters and taking him shopping, strictly for the "aww" factor.
The first rescue-dog candidate was so small a stiff breeze or a confused rabbit could have carried him away.
Winner Winner Chicken Dinner becomes the episode's guiding theme… despite nobody remembering what the winner was or why there was a dinner.
20 Nov 2025
Kiki, Cowboy & the Great Enneagram Mix-Up, Two Types, One Microphone, Zero Preparation
In this episode, Kiki & Cowboy dive head-first into the Enneagram… or the "Any-o-Gram," "Audiogram," "Pain Scale," or whatever Cowboy decides to call it today. What starts as a personality-type discussion quickly turns into the couple hilariously interrupting each other, misquoting psychological concepts, confusing Phil Collins lyrics with life lessons, and accidentally revealing their own quirks in real time.
It's part relationship therapy, part comedy show, and part "Cowboy tries to follow directions while Kiki pulls the car over. Their running game of "who gets to hit the buzzer," this episode is a funny, unfiltered look at personality types…and the personalities that argue about them.
Kiki tries to explain psychology, while Cowboy does everything possible except listen — including Monty Python references and self-appointed buzzer-duty.
They reveal their types (Cowboy: Type 2 with accidental-achiever vibes; Kiki: Type 9 who's maybe a 1, but also maybe an 8… depending on the day).
Cowboy flexes his "Type 3 wing" by reminding the world he recently hosted a gala in a tux and cowboy hat "in front of 400 people… kind of a big deal."
The duo spirals into lovable chaos, proving that no matter the type, their relationship dynamic is the real star: supportive, sarcastic, and laugh-out-loud honest.
Reference:
"You've Got a Type" with Colton Simmons
https://open.spotify.com/episode/6rRCUy8DFdfzb9Rl2IYwfb?si=6f8aa827b1534d99
Key and Peele
https://youtu.be/QmzaPC-iRhQ?si=iVbjEsA2wsipcpWR
20 Aug 2025
Our Hilarious Attempt to Crash the Kid Kraddick Family Vacation
In this episode of Misadventures with Kiki and Cowboy, we learn two very important truths: 1) Kiki should never be underestimated when she wakes up before 7 a.m., and 2) Cowboy should always be suspicious when she does. Kiki hatched a plan involving coffee, scripts, and a morning radio show contest that could win them a Florida vacation with the Kid Kraddick Morning Show. Cowboy thought it was just another one of Kiki’s “wild ideas” (read: potential chaos generators), but before he could even finish his coffee, she had written a full-blown script and was dragging him to rehearse lines like they were auditioning for Broadway.
The comedy really takes off when they start recording their “top nine reasons” they should join the family vacation. Rehearsals sound less like a polished pitch and more like a sitcom blooper reel—misread lines, debates over whether “six kids in college” sounds believable, and Cowboy realizing he’s basically a co-star in Kiki’s unscripted reality show. By the end, they’ve got multiple takes, sound effects, and the kind of marital banter that proves they’d either be the highlight of the vacation or the reason the radio crew never does this contest again. Either way, listeners win.
Top 5 Takeaways:
If Kiki is up before dawn, something is definitely about to happen.
Coffee is not a luxury—it’s survival fuel when married to Kiki.
Writing a “simple 60-second promo” somehow turns into multiple takes, edits, and existential debates about tuition costs.
Cowboy has mastered the art of facepalming as a second language.
Their chaos is precisely why they’d make the perfect guests on a family vacation.
Find the full video here: https://youtu.be/4Albhptqu-E?si=T4Sp8gdYFIrRmGeg
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
Apple Podcasts (US)
5.0 / 5
2 ratings
Spotify
5.0 / 5
4 ratings
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