Ask Smalls Anything: Canceling Plans, Dating Cops & Comment Trolls | Stephie Smalls Show (Ep. 249)

Ask Smalls Anything Episode 15 gets loose fast as Stephie Smalls and Ryan McKee answer questions, rant about modern friendship rules, and explain why adults should be allowed to cancel plans without being treated like they committed emotional arson.

Stephie breaks down whether she would date a cop from Connecticut, tells the story of getting arrested before a John Mayer concert, and ranks the best places to people-watch, including airports, subways, dive bars, bowling alleys, and amusement parks. Ryan gets into boomers and mental health, age-related comment trolls, and why “great looking for his age” is technically a compliment but spiritually a felony.

The episode also gets into Instagram DMs, backhanded compliments, free will, lonely men, Chewy trying to hang out in New York, and why sports bettors need to calm down when someone gives out a long-shot bet like Ravens third in the AFC North. If you like sports, comedy, listener questions, dating stories, and chaotic rants that somehow become life advice, this one is for you.

Follow The Stephie Smalls Show on Spotify for more Ask Smalls Anything episodes, sports betting talk, NFL futures, golf picks, and weekly comedy from Stephie Smalls and Ryan McKee.

SPOTIFY TIMECODES

(00:00) Ask Smalls Anything opens
(00:49) Same hangover returns
(01:37) Canceling plans as adults
(03:03) Boomers and mental health
(06:20) Cop from Connecticut
(08:03) Stephie’s arrest story
(10:41) Best people-watching spots
(12:56) Amusement park people
(13:41) Dive bars and bowling alleys
(14:52) Quick US Open thoughts
(16:14) Scottie Scheffler heater
(16:45) Free will and garbage men
(17:53) Instagram DM strategy
(18:21) Backhanded compliments
(19:24) Age trolls in the comments
(20:46) The Africa lapel pin question
(22:34) Chewy wants to hang out
(23:39) Long-shot betting backlash
(26:14) Keep calling us stupid
(26:39) Football team previews coming

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