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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 improv

All Episodes

58:24

#269 - Choke Me Out

This Square Room ·

2025/12/27

For Deswayne, Tis the Season to be petty. From intimate encounters to hunting down people who have wronged Santa, this episode has it all. So keep your tongue in your mouth as you watch or listen to our final episode for the year 2025.0:00 Intro 0:55 Petty Christmas 2:35 School Is In Session 4:05 Too Much Tongue 6:38 AI Girlfriend 9:27 Rose Toy 11:54 Old School Mentality 16:24 Non-Binary 19:50 Don’t Mean To Offend 24:28 Someone Stabbed Santa 31:48 Realistic Dreams 34:13

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47:19

#268 - Surprise Golden Shower

This Square Room ·

2025/12/18

Jo and Des argue over whether or not they would pleasure themselves if they had the ability and if they would have a sugar mama if the opportunity presented itself.They also chat about first dates, dirty talk gone wrong, embarrassing moments in the bedroom and more. 0:00 Intro 0:16 Quan Millz 11:32 First Dates 16:27 Smashing The Homies 17:53 Sugar Mama 20:53 Scammers 23:17 Storage Jackpot 25:32 Dirty Talk Gone Wrong 29:54 Surprise Golden Shower 34:26 Choked Out 35:49 How To Know If She Loves

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47:23

#267 - Go Suck Yourself

This Square Room ·

2025/12/12

If you had the opportunity to pleasure yourself, would you take it? Jo and Des seem to disagree on how they would go about things. This week they discuss peeing in the shower, having multiple personalities, some interesting statistics and more!0:00 Intro 0:57 Multiple Personalities 7:23 Peeing In the shower 10:39 Siri 11:51 Des’ Phone Update 13:39 Long Lost Son 16:38 Poetry 18:12 Buying Friends Gifts 22:16 Number Of Partners 26:14 Top OF Countries 29:07 Sucking Yourself

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51:51

#266 - Gooning Addiction

This Square Room ·

2025/12/06

Has Deswayne's addiction to gooning gone too far? How do you deliver bad news and is it possible to break up with someone who didn't even know they were dating you? Jo relives an encounter with a bird and Des has broken yet another phone.0:00 intro 0:47 Bird Story 4:32 Pigeons 6:36 Another Broken Phone 9:28 Gooner4Life 28:46 Workplace War 2 34:52 Buffalo Wing Soda 38:17 Bad News 39:28 Imaginary Breakup 45:37 Charity Not Desperation

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38:06

#265 - This Is What You Want, Right?

This Square Room ·

2025/11/22

This week, Des and Jo may give some questionable advice--but this is what you want, right? Unhinged, unfiltered, and a little ridiculous. Jo and Des are here to deliver the good, the bad and the petty.0:00 Intro 0:30 She’s Just Not That Into You 3:44 Work Gossip 8:44 Pickle Soda 12:58 Baby Mamas 13:55 Moving Too Fast 18:36 Rejection 21:57 Communication Fail 24:56 Dive Head First 26:47 Petty Communication 31:10 That’s Not Your Friend

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68:27

264 - It Wasn't Me

This Square Room ·

2025/11/12

Jo realizes that "It wasn't me" is one of the most gaslighting lines ever, as she and Des talk about life changing surgeries, lyrics that they never realized we're very suggestive, and situationships. They also try some more crazy sodas and Des tells a story of a new rival in his life.0:00 Intro 0:47 Happy Birthday 2:38 Gaslighting 5:54 Inappropriate Lyrics 8:46 Change Your Life 10:13 Batman Theory 12:24 Body Enhancements 15:12 Lyrics 16:21 Origin Story 20:13 Terrified In The Water 21:45

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47:56

#263 - Close Your Mouth

This Square Room ·

2025/11/01

This week, as their final halloween costume of the year, Jo and Des challenge their inner pinhead...sort of.Des channels his inner perv--yup, you read that right-- and has a unique strategy when it comes to being trapped in a real life haunted house. The duo talk ghost encounters, couples costumes and when to cut ties with a potential new boo. 0:00 Intro 0:43 Costume Catastrophe 3:13 Surviving in a Haunted House 5:16 Halloween Duo 6:51 Creepy Old Man 10:18 Ghost Ancestors 16:05 Feeling

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41:48

#262 - Below The Belt

This Square Room ·

2025/10/31

Halloween has become a time of year for looking hot and hooking up, and Des has a story all about it! Jo brings up the proper use for hand soap and the duo discuss trust and trust issues. And a hilarious story from a viewer sparks a conversation about clapping back at family members. 0:00 Intro 2:16 Dating On Halloween 5:10 Halloween Hottie 14:04 Hand Soap Scandal 20:13 Trust Issues 32:37 Hit Below The Belt

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25:20

#261 - Break It Off

This Square Room ·

2025/10/31

This week, Jo and Des take the law into their own hands, as they determine if artificial intelligence has finally crossed the line or not. Does a breakup truly count if only one person agrees to it? When does being friendly flirting become cheating? And is it okay to keep an ex's clothing after the relationship has ended? 0:00 Intro 0:32 Des’ New Do 2:43 ChatGPT 3:46 Male Loneliness Epidemic 4:17 Intense AI 10:08 Ex’s Clothing 12:05 Flirting or Friendly? 18:27 Break Up

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30:21

#260 - Totally Killer

This Square Room ·

2025/10/07

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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33:32

#259 - Hard R

This Square Room ·

2025/10/01

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 Venom Is Here 26:37 Hard R

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58:59

#258 - Am I Wrong?

This Square Room ·

2025/09/27

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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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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269 results

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