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This Square Room - Podcast

This Square Room

We’re tired of having to always be politically correct, so we say what we mean, even if it’s taboo.
Your hosts have a comedic perspective on the world as they discuss ANYTHING and EVERYTHING and push boundaries with everyday topics —and push each other’s buttons.
Anything can happen in This Square Room.

Society & Culture Comedy Improv
Update frequency
every 7 days
Average duration
83 minutes
Episodes
256
Years Active
2019 - 2025
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#256 - F*cked, Sucked & Ducked

#256 - F*cked, Sucked & Ducked

Road Trip! This week Jo and Des take a little road trip and get lost, find love in the club and miss a connection all in one eventful weekend.

 

 



0:00 Intro


2:23 Hair Color

6:54 Montreal Trip

01:05:08  |   Fri 29 Aug 2025
#255 - The Price Has Increased

#255 - The Price Has Increased

This week Jo is in over her head as she gets herself into a sticky situation and she shares all of the juicy details. Des is shocked at the list of names that are illegal in the US and the duo discus…

00:56:11  |   Tue 22 Jul 2025
#254 - Black Card Revoked

#254 - Black Card Revoked

Jo becomes an investigative journalist this week when an interesting story (allegedly) falls into her lap.
Des might get his 'Black Card' revoked if he can't remember all of the staple black sayings.…

01:05:31  |   Fri 18 Jul 2025
#253 - Head Game

#253 - Head Game

Jo confronts Deswayne about not having her back when it came to a man. They talk about the kinks Disney characters would have, pleasuring themselves, and why certain people should never give certain …

01:13:17  |   Fri 06 Jun 2025
#252 - Bad Boy

#252 - Bad Boy

This week Jo and Des are back and talking about everything from the birds and the bees to being on the "Down Low" Join them and decide if Des truly can give "sexy eyes" or if Jo is just a hater plus …

01:14:53  |   Wed 28 May 2025
#251 - White-The-Hell?!

#251 - White-The-Hell?!

Des and Jo react to questions that white people have always wanted to ask black people. They also discuss their first crushes, the why having a separate bedroom from your spouse is ideal and why bein…

00:57:07  |   Sat 03 May 2025
#250 - Sounds About WHITE

#250 - Sounds About WHITE

This week, the duo decide which “White People Phrases” are their favourite. Des asks Jo how she would deal with a friendship dilemma and the two give advice on how to get off of an emotional rollerco…

00:54:06  |   Tue 22 Apr 2025
#249 - Culture Clash

#249 - Culture Clash

Jo and Des take a deep drive into why Jamaican men seem take pride in being womanizers and reflect on where they may have gone wrong culturally. They also discuss f*cking vs making love and their per…

01:24:57  |   Sun 20 Apr 2025
#248 - BDSM 101

#248 - BDSM 101

This week Jo and Des invite Saintless onto the podcast to discuss his experience and knowledge of the world of BDSM.

Follow Saintless on TikTok @saintlesschoir and on https://www.youtube.com/ ⁨@saint…

01:47:58  |   Sat 19 Apr 2025
#247 - Touch Of The Tism

#247 - Touch Of The Tism

Embarrassing intimate stories, unsolicited advice and an autism diagnosis. What more could you want in an episode?




0:00 Intro

0:18 Partner vs Child

7:47 Call Me Daddy

10:00 Sh*tty Soda

13:50 Dogg…

01:00:14  |   Wed 09 Apr 2025
#246 - Scratch N Sniff

#246 - Scratch N Sniff

This week is all about phoning a friend because Jo and Des need some outside opinions for some of the interesting things discussed in this episode. Things get a little smelly this week when they disc…

01:09:47  |   Tue 01 Apr 2025
#245 - Power Hour 2

#245 - Power Hour 2

Join Des and Jo for another chaotic power hour.

One shot, every minute for an hour. What could possibly go wrong?

01:58:03  |   Tue 01 Apr 2025
#244 - X-Rated Bucket List

#244 - X-Rated Bucket List

What's on your x-rated bucket list? Find out what's on Des and Jo's lists in this episode and find out their opinions on putting in extra effort in a relationship.

 

 

 

0:00 Intro
1:49 XXX Bucket Li…

00:59:51  |   Thu 13 Mar 2025
#243 - Clutching My Rosary

#243 - Clutching My Rosary

This episode is just as spooky as it is silly. Jo and Des discuss dreams, ghosts, Idiots and more.

 

 

0:00 Intro

1:00 Diddy Krueger

5:27 Sex Sleep Demons

6:54 Sleep Twitching

8:36 Sleep Apnea

12:29 …

00:54:40  |   Sun 09 Mar 2025
#242 - The Full Tea

#242 - The Full Tea

This weeks Deswayne spills his dirty laundry and gets into the nitty gritty of a friendship that blew up.

00:59:33  |   Thu 27 Feb 2025
#241 - No Nut Nathan

#241 - No Nut Nathan

In this week's episode, the hosts talk about party planning, out of body experiences, trouble in the bedroom and more!


 

 

0:00 Intro

0:33 Feb Blues

6:02 The search is over

11:02 Des’ Party

28:08 …

01:05:45  |   Fri 21 Feb 2025
#240 - Dirty Laundry

#240 - Dirty Laundry

This week Jo and Des are truly airing it all out. They play (Extra Dirty) Dirty Laundry and air out secrets they've never spoken about on the podcast, break some new and exciting news, talk about the…

01:24:12  |   Wed 05 Feb 2025
#239 - Puff Puff Pass

#239 - Puff Puff Pass

Jo has learned a new magic trick and tries it on Des. Simp's deserve justice and someone is getting high and it's not who you would expect. And E-LIE-JAH is back and Deswayne isn't happy about it.

00:43:59  |   Thu 30 Jan 2025
#238 - 2nd Time's The Charm

#238 - 2nd Time's The Charm

We're back with a late upload, but better late than never right? In this episode Deswayne discusses a friend who wants a second chance and some drama that went down between some other friends. The du…

00:51:04  |   Thu 30 Jan 2025
#237 - Hear Me Out

#237 - Hear Me Out

Hear us out! This week Jo and Des participate in the hear me out trend where they share fictional characters that they are attracted to. They also discuss getting ghosted by a friend and how to be sn…

00:33:31  |   Tue 15 Oct 2024
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