This Square Room

This Square Room

This Square Room is a weekly podcast bringing laughter and lightheartedness with a fun mix of witty banter, hilarious stories, and offbeat humor. Hosts Jo & Des dive into amusing everyday situations, absurd scenarios, quirky observations and push boundaries with everyday topics —and push each other’s buttons all while keeping the vibe entertaining and hilarious! See more at thissquareroom.com

Episodes

October 7, 2025 30 mins

This week Jo and Des are taking you back to the 80's as they decide which iconic TV killers they could survive against. Then they discuss how they would ruin each others lives if they woke up in each others bodies and Des losing something very important.

 

 

 

0:00 Intro

2:17 Killer Hitlist

16:00 Ruin My Life

20:52 M.I.A.

25:43 All Dogs Go To Heaven

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What goes up, must come down.... right? This week in This Square Room we talk PC culture and the hypocrisy behind which cultures and actions are appropriate to imitate and which ones are not. They discuss the pros and cons of long distance relationships, real life Venom and using the "Hard R"

 

 

 

 

0:00 Intro

2:18 What Goes Up, Must Come Down

4:18 Mispronunciation

5:02 Off Limits Accents

13:32 Long Distance Relationships

21:22 Ve...

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September 27, 2025 58 mins

In This Square Room, when people frustrate us, we cannot be held responsible for any petty actions that may follow. This week Jo and Des ask each other the question, "Am I Wrong?", give advice they are completely unqualified for and then some.

 

 

 

 

0:00 Intro

2:00 Catch Me Outside

5:30 Shared Room Showdown

17:24 Wedding Woes

35:50 Unqualified Advice

43:05 Call It Out

48:14 Petty Party Planning

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September 19, 2025 68 mins

This week Jo and Des play guilty or not guilty, talk about a first date fumble and Des tells the hilarious story of his son's first time getting drunk.

 

 

 

 

0:00 Intro

1:18 Guilty or Not Guilty

2:43 Kiss of Death


11:16 Dumbbell Dummy


14:00 Oh baby

18:40 Truth Hurts 1

9:34 Cake-Tastrophy

22:54 Man Vs Egg

27:13 Let Them Have Cake

29:34 Date Gone Wrong


33:59 Women are the problem

38:15 Name Twins

39:48 First Time Drunk

Mark as Played
August 29, 2025 65 mins

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

7:32 Lost in Montreal


16:21 Road Trip


19:04 After Hours


23:38 Des Finds A Girl

29:16 Jo Finds A Man


46:52 F’ed Sucked Ducked

50:24 Un-Justifiable

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July 22, 2025 56 mins

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 discuss why you should (or shouldn't) lower your expectations when it comes to dating.

 

0:00 Intro

1:08 Spidey v Cap

4:23 Illegal Names

6:32 Santa Claus

9:33 Illegal names cont’d

12:16 USA official language

14:09 Jo’s 4 way

33:09 Ba...

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July 18, 2025 65 mins

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. And the due discuss dating, advice and age gaps. Is age really just a number? Listen now!

 

 

 

0:00 Intro

1:29 Oysters/ Boogers

3:17 Pimples and feet

5:24 Black Card

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June 6, 2025 73 mins

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 people the benefit of the doubt and more in this episode! 0:00 Intro


1:00 Disrespectful Head Game


18:04 Shallow

20:00 Disney Kinks

20:29 Villain Kinks

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May 27, 2025 74 mins

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 so much more!

 

 

0:00 Intro

0:30 Des’ News

3:54 All Gingers Are Black

7:23 The Birds And Bees

9:45 Scary Baby

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May 3, 2025 57 mins

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 being petty just might be the right thing to do in certain situations.

 

 

 

 

 

 

 

0:00 Intro

0:41 Kool-Aid Man

3:07 Dirty Shows/Music

5:00 Crushing

12:25 White-The-Hell

29:52 Separate Rooms

33:44 5am Problems

44:38 Role Reversal

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April 22, 2025 54 mins

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 rollercoaster and end a toxic relationship.

 

 

0:00 Intro

0:23 Sounds about White

19:52 Fake Friend

28:09 Emotional Rollercoaster

3...

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April 20, 2025 84 mins

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 perfect dates.

 

 

 

0:00 Intro

1:16 F*cking vs making love

12:25 Perfect Date

23:41 Culture Clash

28:04 Jamaican Me Crazy


1:16:19 Family Values

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April 19, 2025 107 mins

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/ ⁨@saintlesschoir⁩  

 

 

0:00 Intro

4:55 Des BDSM

12:29 First BDSM Experience

16:31 Kink Community


17:41 Extreme Kinks


19:03 Consensual Non Consent


22:19 Sub Frenzy

27:36 Being Fetishized

32:25 Vore


36:12 3-some Sabotage 


42:22 Power vs ...

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April 9, 2025 60 mins

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 Doggy Style

18:48 Making A Movie

21:56 Embarrassing Sex

35:28 Spinning The Block

37:12 Unsolicited Advice

56:02 Touch of Tism

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April 1, 2025 69 mins

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 discuss a sensitive area, Des tries to talk Jo out of an important decision, and they test their friends loyalty. And this gets paranormal when Des shares an recent incident that happened in his family.

 

Watch the Video Episode and Visit o...

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March 31, 2025 118 mins

Join Des and Jo for another chaotic power hour.

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

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March 13, 2025 59 mins

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 List 20:51 Missing The Spark

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March 9, 2025 54 mins

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 Crazy Baby

19:29 Ghost Jo

21:35 Astral Projecting

23:03 Family Ghost

33:55 Haunted Houses

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February 26, 2025 59 mins

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

Mark as Played
February 21, 2025 65 mins

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 No Nut Nathan

40:40 Denying Pleasure

44:33 Inside Out

45:04 Dirty Do-Over

52:27 Scary dreams

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