Explore every episode of the podcast This Square Room

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 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 Spiritually Humbled

40:25 Giving Up Gooning

41:19 Impossible Commercial

46:29 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 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

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

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 Grass Soda

30:53 Situationships

40:32 Getting in a Fight

45:55 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 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 Pervy 17:45 Summoning Susan 24:14 Couples Costume 30:22 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 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

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

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

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

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 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 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 Intro

0:23 Sounds about White

19:52 Fake Friend

28:09 Emotional Rollercoaster

35:47 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 Intro

0:26 Pinch and Roll

15:28 Pregnancy Scare

30:04 Spin The Block

39:57 Once A Cheater

55:05 Fatherhood 101

57:27 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 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

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 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 Update

1:11:29 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 Reveal

01:37 Hear Me Out

11:54 Ghosting Friends

17:40 Fred Update

21:34 Listener Question

22:56 Snooping on your partner

27:40 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 Reveal

02:13 Pen!s theory

04:07 Starbucks

05:26 Moan Talking

07:09 Strangers Secrets

14:28 Lies

19:49 Movies

27:07 Listener Question

34:52 Melendez Bros

41:36 Uglies

46:17 Cineplex Lawsuit

48:39 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 World

03:02 Love Letter

13:55 Family Reunion

22:12 Broken Electronics

27:30 Not petty

33:35 Listener Question

45:26 Coma

51:44 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 Intro

00:30 Alpha Female

03:30 Crazy S*x

09:30 Pain In The Balls

11:45 Multiple Rounds

14:37 Zoey 101

16:54 Suite Life

17:49 On My Block

21:47 Drake & Josh

22:46 Say No To Drugs

34:40 Trafficked

39:32 Listener Question

40:55 Bad Pu$$y

45:37 Average sex

47:29 Overthinking in the bedroom

49:50 Liar liar

54:32 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?

Is physical or emotional cheating worse? Is age truly nothing but a number? What is the best way to communicate with someone when you are frustrated and have reached your breaking point? Is living with your parents in your mid-twenties a red flag? Jo and Des answer all of these questions and more plus reach to an interesting story about a shocking kinky superpower.

Des has a would you rather question that he can personally relate to and Jo shares her search for the best strip club in North America. The discuss what to do if you embarrass yourself in front of someone you are trying to make a good impression on and Des shares some shocking news.

This week Deswayne faces a rude awakening when he thinks he may have bad breath. Jo and Des answer a listener question that leaves Jo feeling confused and uncomfortable. Des opens up about ending a friendship and the duo react to a TikTok trend.

Fraud, Family betrayal and Fried chicken--this episode has it all. Jonel share a devastating financial loss and Deswayne shares an even more devastating physical and emotional loss in this week's episode.