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
Episodes
Tuesday Feb 03, 2026
Tuesday Feb 03, 2026
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
Wednesday Jan 21, 2026
Wednesday Jan 21, 2026
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
Thursday Jan 15, 2026
Thursday Jan 15, 2026
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
Tuesday Jan 06, 2026
Tuesday Jan 06, 2026
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
Saturday Dec 27, 2025
Saturday Dec 27, 2025
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
Thursday Dec 18, 2025
Thursday Dec 18, 2025
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
Thursday Dec 11, 2025
Thursday Dec 11, 2025
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
Saturday Dec 06, 2025
Saturday Dec 06, 2025
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
Saturday Nov 22, 2025
Saturday Nov 22, 2025
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
Wednesday Nov 12, 2025
Wednesday Nov 12, 2025
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