
Advertise on podcast: This Square Room
Rating
4.8from
This podcast has
279 episodes
Language
EnglishPublisher
Square Room StudiosExplicit
No
Date created
2019/04/28
Latest episode
2026/06/11
Average duration
56 min.
Release period
15 days
Description
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
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Check latest episodes from This Square Room podcast
Free Me Baby #279
2026/06/11
Is ghosting sometimes the RIGHT thing to do? Do people truly want you to be honest with them? After a breakup do you truly miss you ex or do you miss feeling wanted?This week Jo and Des continue their unpopular opinion debates with these topics and more.Des gets called out on his indiscretions and shares a personal situation that he’s recently had to handle.
0:00 intro
0:50 Ghosting Is Sometimes Necessary
4:48 People Miss Feeling Wanted
8:39 Some People Can’t HandleThe Truth
13:28 Your Friends Are Keeping You Single
16:08 Situationships
22:46 J*rking Off With The Dog
27:28 Jizzing On Your Own Face
31:50 Acting Up In School
42:34 Ice Man
#278 - Unpopular Opinions
2026/06/07
Des and Jo find themselves on very opposite sides of some wild unpopular opinions.
0:00 Intro
0:47 Boob or Nip
4:36 Cereal Is A Soup
7:47 Jesus Didn’t Suffer More Than Black People
12:54 Play Fighting Is A Gateway For DV
20:32 Toxic Relationships
24:43 Work Wife/Husband Is Cheating
31:10 Not Everyone Deserves Unconditional Love
39:12 Sharing A Room With A Couple
51:48 Don’t Do It On My Bed
54:34 Desperate Times Call For Desperate Measures
57:30 70 Year Old Purse
59:35 Stop Repeating Yourself
#277 - STFU
2026/04/16
Sometimes people just need to know when to shut the F up! This week Jo holds Des accountable and requests an explanation for something that he said. Des also seeks help from YOU and addresses his mommy issues.
0:00 Intro
0:50 Holding Des Accountable
14:44 Des Needs Our Help
29:47 Mommy Issues
38:12 STFU
47:22 Mom Only Sells Fans
49:29 Zodiac Unlocked
#276 - Intrusive Thoughts
2026/04/08
In this episode, Jo and Des fight against their intrusive thoughts. Des finds out that he might have been secretly tracked plus an update, and Jo and Des discuss who cares more about their public image, who’s more romantic and who is deserving of the “princess treatment”.
0:00 Intro
1:04 I’m Being Tracked
10:40 Public Image
24:13 Who’s More Romantic?
27:17 Intrusive Thoughts
29:35 Princess Treatment
37:22 Des Relationship Update
#275 - Not My Booty!
2026/03/28
This week we find out just how much of a freak one of our hosts is (or isn’t). Jo and Des discuss eating the booty like groceries, micro-peens, how much wood a woodchuck can actually chuck, the joy of missing out and more.
0:00 Intro
0:35 Eat It Like Groceries
15:14 MircoPeen
20:24 Baby Milestones
23:54 How Much Wood?
28:18 Blow Up The Family
34:04 Woodchuck song
35:19 Loneliness Epidemic
42:19 JOMO
#274 - Trouble In Paradise
2026/02/22
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 Intro
1:03 Glory Hole
7:07 Hazardous Waste
10:05 Working With Family
16:26 Sibling Rivalry
22:33 Caught Stealing
30:21 Sibling Fantasy
39:04 Potluck Gatekeeper
45:44 Adding A Third In The Relationship
#273 - Overstayed Welcome
2026/02/03
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
#272 - Family Affair
2026/01/21
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
#271 - F Buddy Contract
2026/01/15
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
#270 - Too Late To Say Sorry?
2026/01/06
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
#269 - Choke Me Out
2025/12/27
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
#268 - Surprise Golden Shower
2025/12/18
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
#267 - Go Suck Yourself
2025/12/12
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
#266 - Gooning Addiction
2025/12/06
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
#265 - This Is What You Want, Right?
2025/11/22
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
Podcast reviews
Read This Square Room podcast reviews
mikeyraccoon 2020/06/27
Deadass amazing podcast
If I’m walking down the street and you go up to me and ask, “What new, unfiltered, funny podcast should I listen to?” I will 1000% say this one. But i...
Fran-Chesca 2019/12/28
YOU MUST LISTEN!
These guys are super honest and funny as hell love the dynamic, really cool.
It's become my go-to at work and during car rides. and I love that they'v...
msimmons81 2019/06/05
Great podcast
I know one of the hosts from youtube. Glad she’s doing a podcast now.
deanbean601 2019/05/22
Good
I enjoyed this more than I expected
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