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Recent episodes
Free Me Baby #279
Jun 11, 2026
49m 57s
#278 - Unpopular Opinions
Jun 7, 2026
1h 05m 24s
#277 - STFU
Apr 16, 2026
58m 49s
#276 - Intrusive Thoughts
Apr 8, 2026
49m 49s
#275 - Not My Booty!
Mar 28, 2026
52m 55s
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| Date | Episode | Topics | Guests | Brands | Places | Keywords | Sponsor | Length | |
|---|---|---|---|---|---|---|---|---|---|
| 6/11/26 | ![]() Free Me Baby #279✨ | ghostinghonesty in relationships+3 | — | — | — | ghostinghonesty+4 | — | 49m 57s | |
| 6/7/26 | ![]() #278 - Unpopular Opinions✨ | unpopular opinionsrelationships+3 | — | — | — | unpopular opinionsrelationships+3 | — | 1h 05m 24s | |
| 4/16/26 | ![]() #277 - STFU✨ | accountabilitymommy issues+2 | — | — | — | STFUhelp+1 | — | 58m 49s | |
| 4/8/26 | ![]() #276 - Intrusive Thoughts✨ | intrusive thoughtspublic image+2 | — | — | — | — | — | 49m 49s | |
| 3/28/26 | ![]() #275 - Not My Booty!✨ | eating the booty like groceriesmicro-peens+2 | — | Eat It LikeBlow Up The Family | — | freakloneliness epidemic+1 | — | 52m 55s | |
| 2/22/26 | ![]() #274 - Trouble In Paradise✨ | relationship issueswork dynamics+2 | — | Working With Family | — | trouble in paradisespeed bump+6 | — | 1h 18m 41s | |
| 2/3/26 | ![]() #273 - Overstayed Welcome✨ | overstayed welcomefunny memories+3 | — | — | — | comedymemories+1 | — | 1h 02m 49s | |
| 1/21/26 | ![]() #272 - Family Affair✨ | family dynamicscolourism+3 | — | Assassinate My Dream | Toronto | blood relationsdoing too much+2 | — | 1h 07m 20s | |
| 1/15/26 | ![]() #271 - F Buddy Contract✨ | friends with benefits contractadult activities+2 | — | — | — | — | — | 1h 02m 16s | |
| 1/6/26 | ![]() #270 - Too Late To Say Sorry?✨ | emotional confrontationDaddy issues+2 | — | Born Again | — | apologiesfamily+1 | — | 46m 45s | |
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| 12/27/25 | ![]() #269 - Choke Me Out✨ | petty Christmasintimate encounters+3 | — | — | — | humorcomedy+2 | — | 58m 24s | |
| 12/18/25 | ![]() #268 - Surprise Golden Shower✨ | self-pleasuresugar mama+3 | — | Smashing The Homies | — | Quan Millzscammers+3 | — | 47m 19s | |
| 12/12/25 | ![]() #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 | — | ||||||
| 12/6/25 | ![]() #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 intro0:47 Bird Story4:32 Pigeons6:36 Another Broken Phone9:28 Gooner4Life28:46 Workplace War 2 34:52 Buffalo Wing Soda38:17 Bad News39:28 Imaginary Breakup45:37 Charity Not Desperation | — | ||||||
| 11/22/25 | ![]() #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 Intro0:30 She’s Just Not That Into You3:44 Work Gossip8:44 Pickle Soda12:58 Baby Mamas13:55 Moving Too Fast18:36 Rejection21:57 Communication Fail24:56 Dive Head First26:47 Petty Communication31:10 That’s Not Your Friend | — | ||||||
| 11/12/25 | ![]() 264 - It Wasn't Me | 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 Intro0:47 Happy Birthday2:38 Gaslighting5:54 Inappropriate Lyrics8:46 Change Your Life10:13 Batman Theory12:24 Body Enhancements15:12 Lyrics16:21 Origin Story20:13 Terrified In The Water21:45 Grass Soda30:53 Situationships40:32 Getting in a Fight45:55 Workplace War | — | ||||||
| 11/1/25 | ![]() #263 - Close Your Mouth | 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 Intro0:43 Costume Catastrophe3:13 Surviving in a Haunted House5:16 Halloween Duo6:51 Creepy Old Man10:18 Ghost Ancestors16:05 Feeling Pervy17:45 Summoning Susan24:14 Couples Costume30:22 New Man | — | ||||||
| 10/31/25 | ![]() #262 - Below The Belt | 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 Intro2:16 Dating On Halloween5:10 Halloween Hottie14:04 Hand Soap Scandal20:13 Trust Issues32:37 Hit Below The Belt | — | ||||||
| 10/31/25 | ![]() #261 - Break It Off | 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 Intro0:32 Des’ New Do2:43 ChatGPT3:46 Male Loneliness Epidemic4:17 Intense AI10:08 Ex’s Clothing12:05 Flirting or Friendly?18:27 Break Up | — | ||||||
| 10/7/25 | ![]() #260 - Totally Killer | 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 Intro2:17 Killer Hitlist16:00 Ruin My Life20:52 M.I.A.25:43 All Dogs Go To Heaven | — | ||||||
| 10/1/25 | ![]() #259 - Hard R | 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 Intro2:18 What Goes Up, Must Come Down4:18 Mispronunciation5:02 Off Limits Accents13:32 Long Distance Relationships21:22 Venom Is Here26:37 Hard R | — | ||||||
| 9/27/25 | ![]() #258 - Am I Wrong? | 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 | — | ||||||
| 9/19/25 | ![]() #257 - Guilty AF | 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 | — | ||||||
| 8/29/25 | ![]() #256 - F*cked, Sucked & Ducked | 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 | — | ||||||
| 7/22/25 | ![]() #255 - The Price Has Increased | 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 | — | ||||||
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