This Square Room

Square Room Studios
  • 4.9 (15)
  • IMPROV
  • UPDATED BIWEEKLY

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

  1. JAN 21

    #272 - Family Affair

    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

    1h 7m

  2. JAN 15

    #271 - F Buddy Contract

    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

    1h 2m

  3. JAN 6

    #270 - Too Late To Say Sorry?

    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

    47 min

  4. 2025-12-27

    #269 - Choke Me Out

    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

    58 min

  5. 2025-12-18

    #268 - Surprise Golden Shower

    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

    47 min

  6. 2025-12-12

    #267 - Go Suck Yourself

    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

    47 min

  7. 2025-12-06

    #266 - Gooning Addiction

    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

    52 min

  8. 2025-11-22

    #265 - This Is What You Want, Right?

    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

    38 min
See All (272)

4.9
out of 5
15 Ratings

About

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

Information

  • Creator
    Square Room Studios
  • Years Active
    2019 - 2026
  • Episodes
    272
  • Rating
    Explicit
  • Copyright
    © Copyright 2019 All rights reserved.
  • Show Website
    This Square Room