This Square Room

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