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PODCAST

This Square Room

Square Room Studios

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

comedy

All Episodes

68:03

#257 - Guilty AF

This Square Room ·

2025/09/19

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

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01:05:08

#256 - F*cked, Sucked & Ducked

This Square Room ·

2025/08/29

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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56:11

#255 - The Price Has Increased

This Square Room ·

2025/07/22

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 Bad hygiene 39:40 Lower Your Expectations

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01:05:31

#254 - Black Card Revoked

This Square Room ·

2025/07/18

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 19:00 Des is a Stud 20:55 Caught in Drama 35:50 Dating Advice 43:08 Age Ain't Nothing But A Number 48:40 Hot Water Incident 57:31 The

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01:13:17

#253 - Head Game

This Square Room ·

2025/06/06

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 27:25 Sidekick Kinks 30:12 Main Character Kinks 33:05 Gaslighting 101 44:41 Listener Question 45:51 No Benefit Of The Doubt 54:02

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01:14:53

#252 - Bad Boy

This Square Room ·

2025/05/28

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 13:54 Sexy Eyes 25:30 Teenage Stalker 45:14 DL BF 49:24 Dying Wish 59:52 Tory Lanes 1:03:26 Bad Boy

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57:07

#251 - White-The-Hell?!

This Square Room ·

2025/05/03

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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54:06

#250 - Sounds About WHITE

This Square Room ·

2025/04/22

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 35:47 Love The Way You Lie

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01:24:57

#249 - Culture Clash

This Square Room ·

2025/04/20

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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01:47:58

#248 - BDSM 101

This Square Room ·

2025/04/19

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 Control 53:32 Role Reversal 1:04:54 Egalitarian kink 1:10:54 Forever

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01:00:14

#247 - Touch Of The Tism

This Square Room ·

2025/04/09

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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01:09:47

#246 - Scratch N Sniff

This Square Room ·

2025/04/01

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 our socials here: https://linktr.ee/thissquareroom 0:00 Intro 0:26

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01:58:03

#245 - Power Hour 2

This Square Room ·

2025/04/01

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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59:51

#244 - X-Rated Bucket List

This Square Room ·

2025/03/13

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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54:40

#243 - Clutching My Rosary

This Square Room ·

2025/03/09

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 42:08 Dream meanings 51:09 Idiots

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59:33

#242 - The Full Tea

This Square Room ·

2025/02/27

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

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01:05:45

#241 - No Nut Nathan

This Square Room ·

2025/02/21

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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01:24:12

#240 - Dirty Laundry

This Square Room ·

2025/02/05

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 recent games night video and also play a fun drinking game. Prepare for an unhinged episode.0:00 Intro 1:10 Game Night 2:19 Cheating 3:16 Behind the scenes 8:27 TRASH 12:18 Dirty Laundry Game 26:21 Dumster 28:58 More Dirty Laundry 38:18 Hooking up in friends bed 46:56 Announcement 53:29 Fred

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43:59

#239 - Puff Puff Pass

This Square Room ·

2025/01/30

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.

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51:04

#238 - 2nd Time's The Charm

This Square Room ·

2025/01/30

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 duo also discuss what they would do if they woke up in the body of the opposite gender.

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277 results

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