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 Intro

0:32 Des’ New Do

2:43 ChatGPT

3:46 Male Loneliness Epidemic

4:17 Intense AI

10:08 Ex’s Clothing

12:05 Flirting or Friendly?

18:27 Break Up

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 Intro

2:17 Killer Hitlist

16:00 Ruin My Life

20:52 M.I.A.

25:43 All Dogs Go To Heaven

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 Intro

2:18 What Goes Up, Must Come Down

4:18 Mispronunciation

5:02 Off Limits Accents

13:32 Long Distance Relationships

21:22 Venom Is Here

26:37 Hard R

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

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

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.

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

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.

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

Jo becomes an investigative journalist this week when an interesting story (allegedly) falls into her lap.

0:00 Intro

1:29 Oysters/ Boogers

3:17 Pimples and feet

5:24 Black Card

19:00 Des is a Stud

20:55 Caught in Drama

35:50 Dating Advice

43:08 Age Ain't Nothing But A Number

48:40 Hot Water Incident

57:31 The Last Of Us

58:54 Tory Lanes

Jo confronts Deswayne about not having her back when it came to a man. They talk about the kinks Disney characters would have, pleasuring themselves, and why certain people should never give certain people the benefit of the doubt and more in this episode!

1:00 Disrespectful Head Game


18:04 Shallow

20:00 Disney Kinks

20:29 Villain Kinks

27:25 Sidekick Kinks

30:12 Main Character Kinks

33:05 Gaslighting 101

44:41 Listener Question


45:51 No Benefit Of The Doubt

54:02 Masturbation


01:09:14 Love Over Money

This week Jo and Des are back and talking about everything from the birds and the bees to being on the "Down Low" Join them and decide if Des truly can give "sexy eyes" or if Jo is just a hater plus so much more!

0:30 Des’ News

3:54 All Gingers Are Black

7:23 The Birds And Bees

9:45 Scary Baby

13:54 Sexy Eyes

25:30 Teenage Stalker

45:14 DL BF

49:24 Dying Wish

59:52 Tory Lanes

1:03:26 Bad Boy