The JTrain Podcast: "MidBEST or MidAtBest with Taylor Kay Phillips – CHIT CHAT WEDNESDAY"

Date: September 24, 2025
Host: Jared Freid
Guest: Taylor Kay Phillips

Episode Overview

This "Chit Chat Wednesday" episode features comedian, writer, and Emmy winner Taylor Kay Phillips, author of the newly released A Guide to Midwestern Conversation. Host Jared Freid—joined by Taylor in her hometown of Kansas City—dives deep into book writing collaboration, cultural linguistics, and the puzzles of comedic and Midwestern communication. The episode blends behind-the-scenes commentary on writing, playful Midwestern phrase quizzes, and a game assessing regional traditions.

Key Discussion Points & Insights

1. The Book-Writing Journey

• Collaboration Dynamics:
  • Jared describes the struggles of writing his upcoming dating advice book, culminating in seeking a "ghostwriter," but Taylor prefers the term "book coach" or "translator" for their partnership.

    "You wrote stuff and then I made a book." — Taylor Kay Phillips [05:14]

  • Taylor attributes their success to mutual willingness to collaborate, compare comedic structure, and honestly discuss what works.
• Translating Comedy to the Page:
  • They discuss navigating the differences between spoken comedy and the written word, emphasizing the need for structure and storytelling in a book that differs from stage performance.

    "Figuring it out. This is one big puzzle. Every day it works my brain, I get this satisfaction when it does work." — Jared Freid [10:00]

• Personal Storytelling:
  • Both explore vulnerability in writing, reflecting on the challenge of revisiting personal stories and the importance of authenticity in dating advice.
  • Taylor expresses the strange intimacy of becoming the first reader and critic of Jared's stories:

    "On the one hand, I don't know you like that, and on the other hand, I'm the only person who knows you like that." — Taylor [16:26]

2. Midwestern Language & Culture: Book Insights

• Midwestern Euphemisms vs. Honesty:

  • Taylor rejects the label of Midwesterners as indirect:

    "We are saying what we mean, but this is how we say it. If I say, 'that person is a character,' ...I am saying in my Midwestern language that woman is absolutely batshit." [21:16]

• Decoding Phrases Quiz:

  • Jared quizzed Taylor on identifying the literal and subtextual meanings in seemingly ambiguous Midwestern replies ("yeah, no," "no, yeah, no," etc.).
  • Taylor's explanations highlight Midwest nuance—affirmations, polite refusals, and softening directness:
    • "Yeah, no" = no. [22:10]
    • "No, yeah" = yes. [22:49]
    • "Yeah, no, yeah" = yes, affirmative. [23:20]
    • "No, yeah, no" = a polite but undeniable no; sometimes a little shade. [24:23]

• Midwestern Nice:

  • Both reject "fake nice" stereotypes, emphasizing how politeness coexists with emotional range and directness, but within politer boundaries:

    "Minnesota nice is not, 'they're also nice.' ... The floor and ceiling of the actual words that they use are different, so you have to calibrate, but the extremity is the same." — Taylor [27:07]

3. Culture Clash: Midwest Meets New York

• Assimilating Regional Identity:
  • Taylor reflects on feeling "the nicest girl in New York and a cutthroat bitch in the Midwest" [28:23], showing how regional norms recalibrate one’s perceived personality.
• Gender & Behavioral Expectations:
  • The pair discuss double-standards in expectations of maturity and politeness for women versus men growing up in the Midwest.

    "There was a sense of like, I should know better, but also if I knew too much better, I was being disrespectful." — Taylor [32:49]

Memorable Quotes & Moments

• Jared on Comedy as a Puzzle:

  "I've been coming… people ask me a lot about being a comedian… I love the puzzle. Figuring it out. This is one big puzzle." [10:00]

• Taylor on Midwestern Indirectness:

  "We're not speaking in code. This is just Midwestern." [21:16]
  "Minnesota nice is not 'oh, they're so nice,' it's… the words are different, the extremity is the same." [27:07]

• On Ghostwriting:

  "I'm ghostwriter in the way like the movie... your hands are on it, and it's me behind you being like, 'let's make a little ridge.'" — Taylor [05:58]

Segment Timestamps

• [00:00–07:40]: Introduction; Kansas City origins; book-writing partnership; challenges and process insights
• [07:40–12:48]: Collaboration mechanics and translation of comedy to the page; role of feedback and vulnerability
• [12:48–19:59]: Shared language in comedy; how a collaborative process impacts the book’s voice and concepts (e.g., redefining "the reveal" in dating)
• [20:31–28:09]: Taylor’s book; culturally decoding Midwestern language; euphemisms, honesty, and softening communication
• [21:45–25:31]: Midwestern phrase quiz ("yeah, no"/"no, yeah" etc.)
• [25:31–27:07]: Discussion on “Midwestern nice” and the full spectrum of behavior in the region
• [28:09–33:10]: Leaving and returning to the Midwest; gender, politeness, and behavioral expectations
• [33:10–51:04]: Game: "Midwest or Mid Best (Mid at Best)"; rating Midwestern traditions and foods (Puppy Chow, cornhole, pop, gooey butter cake, ranch, casserole/hot dish); exploration of local verbiage and customs

Games & Feature Segments

“Midwest or Mid Best (or Mid at Best)” [33:53–51:04]

Jared presents Taylor with iconic Midwestern foods, traditions, and vocabulary. Taylor decides if each is “the best” or “mid at best,” providing cultural insight and personal anecdotes.

Highlighted Items:

• Puppy Chow: Unanimous “the best”; celebrated for delicious messiness and nostalgia. [34:31–36:54]
• Cornhole: “Mid at best”; fun, but surpassed by other games like horseshoes. [37:17–39:44]
• Pop (vs. Soda): Debated, but largely a non-issue among Midwesterners. [39:56–41:18]
• Gooey Butter Cake: “The best”; compared to milk bar pie; decadent, sugary dessert. [41:49–43:39]
• Ranch Dressing: “The best” for Taylor, less so for Jared; ranch on pizza a regional staple. [44:09–45:51]
• Casserole/Hot Dish: Nuanced; some are great, others aren’t. Casserole’s PR problem versus “hot dish” rebranding. Cultural mixing of foods (including references to kugel and lasagna as classified casseroles) [46:01–50:09]

Final Thoughts & Guest Plugs

• Taylor’s book A Guide to Midwestern Conversation is available now—a humorous, affectionate guide to regional etiquette and linguistic code. [19:59, 47:44, 50:30]
• Follow Taylor on Instagram and social media (@TaylorKPhillips).

Summary in Tone

The episode is marked by playful banter, relatable confessions about writing and self-doubt, lots of hearty Midwest affection, and comedic riffs on language and food. Both Jared and Taylor are open, self-deprecating, and collaborative, making even their analysis of regional quirks deeply engaging and warm.

Listen For

• Insider takes on writing comedy books ([04:13–07:07])
• A comedic masterclass in decoding Midwestern speech ([21:15–25:31])
• Playful regional rivalries and why some traditions endure ([34:31–50:09])
• Reflections on gendered experiences growing up Midwest ([29:56–33:10])

Skip to [33:53–51:04] for the Midwest food and tradition debate; [21:45–25:31] for the phrase quiz; [07:40–19:59] for book-writing insights; and [25:31–27:07] for the in-depth discussion of "Midwestern nice".