This Square Room

Sometimes people just need to know when to shut the F up! This week Jo holds Des accountable and requests an explanation for something that he said. Des also seeks help from YOU and addresses his mommy issues.0:00 Intro0:50 Holding Des Accountable14:44 Des Needs Our Help29:47 Mommy Issues38:12 STFU47:22 Mom Only Sells Fans49:29 Zodiac Unlocked

In this episode, Jo and Des fight against their intrusive thoughts. Des finds out that he might have been secretly tracked plus an update, and Jo and Des discuss who cares more about their public image, who’s more romantic and who is deserving of the “princess treatment”.0:00 Intro1:04 I’m Being Tracked10:40 Public Image24:13 Who’s More Romantic?27:17 Intrusive Thoughts29:35 Princess Treatment37:22 Des Relationship Update

This week we find out just how much of a freak one of our hosts is (or isn’t). Jo and Des discuss eating the booty like groceries, micro-peens, how much wood a woodchuck can actually chuck, the joy of missing out and more.0:00 Intro0:35 Eat It Like Groceries15:14 MircoPeen20:24 Baby Milestones23:54 How Much Wood?28:18 Blow Up The Family34:04 Woodchuck song35:19 Loneliness Epidemic 42:19 JOMO

There’s trouble in paradise for Deswayne as he opens up about a new speed bump in his relationship. The duo also chat about work dynamics, sibling rivalries and the usual nonsense that we all know and love.0:00 Intro1:03 Glory Hole7:07 Hazardous Waste10:05 Working With Family16:26 Sibling Rivalry 22:33 Caught Stealing30:21 Sibling Fantasy39:04 Potluck Gatekeeper45:44 Adding A Third In The Relationship

This week we find out what Jo and Des will do when someone overstays their welcome. The duo reminisce on old "funny-not-so-funny" memories, and Deswayne has an epiphany. 0:00 Intro 0:42 Once a hoe always a hoe 2:00 No Longer Green 3:45 RolePlay 26:30 Overstayed Welcome 28:00 Not-So-Funny School moments 46:05 Listener Question 53:38 Deswayne’s Dream

Blood isn't always thicker than water, and what happens in the family can sometimes ruin lives. This week, Jo and Des expose shocking secrets, discuss colourism, doing too much in relationships, what went down in Des' DMs, what the name of a Toronto-based super hero would be and more. 0:00 Intro 0:28 Toronto Superhero 2:52 Assassinate My Dream 11:02 Skin Tone 18:40 6 Wives 24:44 Fire Drills 27:05 Old Friends & Old Flames 31:17 Family Affair 48:53 Doing Too Much 54:34 It Goes Down In The DMs 1:02:38 Cheating Rag Doll

This week Jo, Des and the OG roommates get a blast from the past!
They discuss a friends with benefits contract, the first time dipping your toe into adult activities, hypocritical church goers, strange habits and more. 0:00 Intro 0:26 CockPit 7:53 CocoNUT 10:02 67 12:53 FWB Contract 22:17 First Time For Everything 26:36 Messy Bessy 41:52 Jumping To Conclusions 45:38 Fred Is Free 55:22 Sinners

Is it too late to say sorry? This week we have an emotional confrontation but not before Jo and Des chat about Daddy issues, marriage proposals, who really hold the power in a relationship and more! 0:00 Intro 0:55 Resolutions 3:50 Say No To Proposals 7:26 On Who’s Terms? 11:16 Family Photo Redemption 15:55 Family Disappointment 18:46 Born Again 21:49 Daddy Issues 27:28 Role Play Gone Wrong 32:46 Too Late To Say Sorry

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 Intro0:55 Petty Christmas2:35 School Is In Session4:05 Too Much Tongue6:38 AI Girlfriend9:27 Rose Toy11:54 Old School Mentality16:24 Non-Binary19:50 Don’t Mean To Offend24:28 Someone Stabbed Santa31:48 Realistic Dreams34:13 Spiritually Humbled40:25 Giving Up Gooning41:19 Impossible Commercial46:29 Petty Coworker

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 You

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

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 intro0:47 Bird Story4:32 Pigeons6:36 Another Broken Phone9:28 Gooner4Life28:46 Workplace War 2
34:52 Buffalo Wing Soda38:17 Bad News39:28 Imaginary Breakup45:37 Charity Not Desperation

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 Intro0:30 She’s Just Not That Into You3:44 Work Gossip8:44 Pickle Soda12:58 Baby Mamas13:55 Moving Too Fast18:36 Rejection21:57 Communication Fail24:56 Dive Head First26:47 Petty Communication31:10 That’s Not Your Friend

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 Intro0:47 Happy Birthday2:38 Gaslighting5:54 Inappropriate Lyrics8:46 Change Your Life10:13 Batman Theory12:24 Body Enhancements15:12 Lyrics16:21 Origin Story20:13 Terrified In The Water21:45 Grass Soda30:53 Situationships40:32 Getting in a Fight45:55 Workplace War

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 Intro0:43 Costume Catastrophe3:13 Surviving in a Haunted House5:16 Halloween Duo6:51 Creepy Old Man10:18 Ghost Ancestors16:05 Feeling Pervy17:45 Summoning Susan24:14 Couples Costume30:22 New Man

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 Intro2:16 Dating On Halloween5:10 Halloween Hottie14:04 Hand Soap Scandal20:13 Trust Issues32:37 Hit Below The Belt

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 Intro0:32 Des’ New Do2:43 ChatGPT3:46 Male Loneliness Epidemic4:17 Intense AI10:08 Ex’s Clothing12:05 Flirting or Friendly?18:27 Break Up

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 Intro2:17 Killer Hitlist16:00 Ruin My Life20:52 M.I.A.25:43 All Dogs Go To Heaven

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 Intro2:18 What Goes Up, Must Come Down4:18 Mispronunciation5:02 Off Limits Accents13:32 Long Distance Relationships21:22 Venom Is Here26:37 Hard R

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

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

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

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

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 Last Of Us 58:54 Tory Lanes

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 Shallow20:00 Disney Kinks20:29 Villain Kinks27:25 Sidekick Kinks30:12 Main Character Kinks33:05 Gaslighting 10144:41 Listener Question
45:51 No Benefit Of The Doubt54:02 Masturbation
01:09:14 Love Over Money

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

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

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 Intro0:23 Sounds about White19:52 Fake Friend28:09 Emotional Rollercoaster35:47 Love The Way You Lie

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

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 Lead 1:17:17 Beginner Advice

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

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 Intro0:26 Pinch and Roll15:28 Pregnancy Scare30:04 Spin The Block39:57 Once A Cheater55:05 Fatherhood 10157:27 Possessed By Peter 

Join Des and Jo for another chaotic power hour. One shot, every minute for an hour. What could possibly go wrong?

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

This episode is just as spooky as it is silly. Jo and Des discuss dreams, ghosts, Idiots and more.  0:00 Intro1:00 Diddy Krueger5:27 Sex Sleep Demons6:54 Sleep Twitching8:36 Sleep Apnea12:29 Crazy Baby19:29 Ghost Jo21:35 Astral Projecting23:03 Family Ghost33:55 Haunted Houses42:08 Dream meanings51:09 Idiots

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

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

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 Intro1:10 Game Night2:19 Cheating3:16 Behind the scenes8:27 TRASH12:18 Dirty Laundry Game26:21 Dumster28:58 More Dirty Laundry38:18 Hooking up in friends bed46:56 Announcement53:29 Fred Update1:11:29 Old Tea

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.

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.

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 sneaky and catch someone doing something they shouldn't be doing!   00:00 Costume Reveal01:37 Hear Me Out11:54 Ghosting Friends17:40 Fred Update21:34 Listener Question22:56 Snooping on your partner27:40 Catching A Cheater

Should some secrets stay private? This week, Jo and Des literally swap places as they discuss secrets, theories, movies and more.    00:00 Costume Reveal02:13 Pen!s theory04:07 Starbucks05:26 Moan Talking07:09 Strangers Secrets14:28 Lies19:49 Movies27:07 Listener Question34:52 Melendez Bros41:36 Uglies46:17 Cineplex Lawsuit48:39 Turned tables

This week Jo and Des are kicking off spooky season with a throw back that's sure to make you laugh. Jo reads a special letter written to Deswayne, they take a trip down memory lane, Des shares about his family reunion and more.   00:00 Wayne’s World03:02 Love Letter13:55 Family Reunion22:12 Broken Electronics27:30 Not petty33:35 Listener Question45:26 Coma51:44 Memory Lane 

Are the crazy ones actually better in bed? This week Jonel and Deswayne talk about being an alpha, why being average in bed is better than being great, drugs, a real life trafficking story and more. 00:00 Intro00:30 Alpha Female03:30 Crazy S*x09:30 Pain In The Balls11:45 Multiple Rounds14:37 Zoey 10116:54 Suite Life17:49 On My Block21:47 Drake & Josh22:46 Say No To Drugs34:40 Trafficked39:32 Listener Question40:55 Bad Pu$$y45:37 Average sex47:29 Overthinking in the bedroom49:50 Liar liar54:32 Embarrassing Dance

Jo & Des have found themselves at odds this week as they bicker and take shots at each other because of recent poll results-- let's hope none of this goes to their heads! In this episode duo are thrown for a loop when they discuss the woman equivalent of "Where's my hug?" an absolutely crazy hook up experience, the most embarrassing thing that has happened to them while being intimate, family issues and a wild news story.   00:00 Intro 00:42 Yapper Poll 2:53 Pillow F’er 4:52 Yapper Poll results 7:45 Where’s My Hug? 15:36 Club Hook Up 21:33 Big Head Bickering 28:59 Embarrassing s*x 37:00 Go “Fishing” 42:09 Family Issues 50:39 Eel Story

This week Des learns some unexpected news about Jo. Jo and Des find themselves at odds as they discuss the ugly truth of how society views women, and they both get passionate about "Fred" and Deswayne's petty prodigy. 00:19 Hello Kitty 3:53 Adult movie posters 18:38 Jo's Toys 25:40 Petty Prodigy 36:00 Fred Update 43:12 Listener Question 45:18 Low Value Women

Pettiness prevails in this weeks episode as Jo and Des discuss a recurring sore spot for Deswayne and the duo find themselves on opposing sides of a conversation.

Jo and Des discuss the Paris Olympics, Trump, give some advice to hopefully free a man in an unfortunate situation and more in this episode.

Jonel and Deswayne play Guilty or Not Guilty in this amusing episode of This Square Room.

Liar liar pants on fire, Jonel and Deswayne confront a listener who they believe might be hiding something. Des went M.I.A. and has some explaining to do. Everybody has heard of "Hawk Tuah", but is it overrated?