This Square Room

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.

0:28 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.

0:26 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!

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.

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!

0:57 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