O.J. Galloway and Ressie G.
Casually Deep: The Podcast
A dynamically curated podcast of commonly discussed situations explored between two friends who take the most casual segways into the deepest of dialogues. Join Ressie G., and Oaklyn Jonas Galloway as they journey the depths of the mind, through simplest of subjects.
Author
O.J. Galloway and Ressie G.
Category
Podcast website
Latest episode
Jun 1, 2026
Where to listen?
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Episodes
Pride Month: Tales, Tips, and Tricks 01.06.2026 39:34
In Episode 8 of Season 2 of Casually Deep The Podcast, the hosts kick off Pride Month with a conversation about what Pride means today and how to navigate the celebrations, culture, and community that come with it. Ressie G. shares 5 essential tips for surviving and thriving during Pride, from staying safe and setting boundaries to making meaningful connections and enjoying the experience authenti...
Do People Take Accountability? 19.04.2026 1:01:58
Accountability or comfort… which one are you choosing? In this episode of Casually Deep The Podcast, we unpack what it really means to take accountability versus staying stuck in habits and mindsets, and why some people grow when they’re called out while others double down. We also get into what it means to be triggered, is it a defense mechanism or an opportunity for deeper self-awareness? This c...
Black Token Gay 05.04.2026 1:09:20
In this episode of Casually Deep The Podcast, we dive into the complexities of interracial dating within the Black gay community, unpacking the dynamics between Black gay men and white gay men while exploring ideas around attraction, preference, and the theory of tokenism in modern dating spaces—questioning whether these connections are rooted in genuine interest, social conditioning, or something...
Casual Chat: Part One 21.03.2026 1:08:51
In Episode 4 of Season 2 of Casually Deep The Podcast, the hosts turn the spotlight on you as they answer real questions straight from viewers. From relationships and dating to personal growth, identity, and life experiences, no topic is off limits. Ressie G. and Oaklyn dive deep into each question, offering honest perspectives, unfiltered opinions, and meaningful conversation that goes beyond sur...
Tops v Bottoms: Heteronormative Constructs 13.03.2026 1:14:37
In this episode of Casually Deep The Podcast, 🍑🍆 Top Privilege or just a double standard? In this episode of Casually Deep The Podcast, we’re unpacking the conversation that always gets the group chat going. Why is it that tops can have multiple partners and be called players… but bottoms get shamed for the same thing?🤔Ressie G opens up about navigating life as a bottom while never having been...
Do You Have To Have Sex Just To Cuddle? 13.03.2026 1:13:36
In Episode 3 of Season 2 of Casually Deep The Podcast, Ressie G. and Oaklyn-Jonas Galloway unpack the idea that in today’s LGBTQ dating culture, many gay men feel like they have to have sex just to experience basic intimacy like cuddling or affection. The conversation explores how hookup culture can blur the line between physical access and genuine emotional connection, while also highlighting how...
“OAKLYN POPPED MY CHERRY” -Ressie G. 27.02.2026 1:05:32
In our Season 2 premiere, we’re catching up on what’s been happening in our off season, give you all updates on what we’ve been up to since season one and take a look back at some of our most important conversations from season one with fresh eyes and new perspectives. Some things we double down on and some we take a new approach to. The excitement for this new era is truly palpable and our chemis...
Thee 1on1: Part Two 18.07.2025 21:18
In the conclusion to our most dynamic conversation of the season, as well as the season as a whole, Ressie and OG wind down the last of their 1 on 1 QnA. They analyze the dynamics of their friendship, discuss their journeys in the media and web reality space both past and future, and solidify not only there working relationship, but the friendship that they have cultivated from it. This season has...
Casting Our Fantasy Talk Shows 11.07.2025 26:55
In today’s Casual Conversation, the hosts Deep Dive into Talk Shows!!! Today’s episode dives into Ressie and OG’s favorite pastimes, TALK SHOWS. The hosts are diving into their producer bags and conceptualizing original ideas for new talk shows launches and giving you all a panel of hosts guaranteed to make you think, as well as check your local listings! Ressie G. begins with a a group of six hos...
Thee 1on1: Part One 11.07.2025 1:01:36
In the two part season one finale, Ressie G. and OG take a different Deep Dive to the Casual Conversation. The conversation opens with a peeling of the onion in regards to the hosts friendship. They go back in time and lay the foundation to not only a dynamic working relationship, but an even more meaningful friendship that has transcended cameras. In part one, the hosts play 22 questions and give...
Love and Loss 11.07.2025 24:50
In today’s Casual Conversation, the hosts Deep Dive into Love and Loss!!! Today’s episode dives into Ressie and OG’s experience with love, loss, and everything in between! The hosts reflect on their love lives, and the things they’ve learned, wish they never learned, and advice they have for each other and you all tuning in. Enjoy the trip down memory lane as these two single men take you on a pat...
Soundtracks to Millennial Lives 06.06.2025 34:28
In today’s Casual Conversation, the hosts Deep Dive into Our Millennial Soundtracks In today’s episode, Ressie and OG are dissecting the Millennial Experience and revisiting albums that helped shape our core memories and still hold special places in our hearts. In a top ten countdown organize their own list from those album that were either released or primarily important during their coming of ag...
The Web Reality World 31.05.2025 1:00:39
In today’s Casual Conversation, the hosts Deep Dive into The INEVITABLE conversation about WEB REALITY. Ressie G. opens a discussion on Executive Producers having a place in the cast of their shows. In this segment, they chat about their varied experiences personally in the web reality genre both in front on and behind the camera’s lens. Ressie G. expounds on the difference between Ressie the Cast...
What is True Desirability? 16.05.2025 41:07
In today’s Casual Conversation, the hosts Deep Dive into the true meaning of desirability OG opens a debate with Ressie on fetshism and whether it not it has an inherent strand in the DNA of attraction. In this segment, they chat about their own experiences with featurism, the narratives and assumptions black men face in the dating world, OG puts some of his own attractions on the table, Ressie di...
Ms. Bravo… OK GIRL!!! 09.05.2025 1:13:48
On this week’s episode Ressie G. and OG are opening up the Reality Rehab in an exclusive expanded segment to talk RHOA, Next Generation NYC and all things Bravo and Reality TV. Starting off with Brit Eady vs Kenya Moore the hosts dive into the complexities and nuances of the entire situation. Ressie gives a brief timeline of all events leading up to “The Incident” that led to Kenya’s departure. OG...
Black Culture F*CK’d UP Black Men 09.05.2025 1:05:52
In today’s Casual Conversation, the hosts Deep Dive into Black Culture’s effects on the Black Man. The episode starts with a debate on the current state of the modern black family, the lack of patriarchal presence in the home, and which party the hosts deem responsible. OG opens a discussion on whether the mother or father holds more responsibility, and things get interesting from the JUMP! The co...
Dream Celebrity Questions 01.05.2025 49:53
In today’s Casual Conversation, the hosts Deep Dive into their Dream Celebrity Questions. Ressie G. opens the discussion on the people we idolize and are inspired by. In this episode, they chat about the people who have informed their dreams, inspired them as people or are attached to core memories they carry deep down. In a back and forth, the ramble off the questions that they’ve always imagined...
How to Date a Gay 18.04.2025 50:55
In today’s Casual Conversation, the hosts Deep Dive into How to Date a Gay. Ressie G. opens a discussion on gay couples and dependency on heteronormativity. In this segment, they chat about OG’s experiences in his previous marriage. He articulates how this dynamic worked within his marriage and if it played into the demise of his marriage , OG opens the floor to share their perspectives on navigat...
Tiffany Box Questions 05.03.2025 45:09
In today’s Conversation, we are getting into some Casual Questions with Deep Answers. Ressie opens the episode with a short trip down memory lane. He breaks down the origin the infamous Tiffany box, and lets you all know the layout of today’s episode. We are opening the floor to your questions and some of our own! We get to reminisce about some of the most interesting moments and our life, share s...
Why are men Still DL? 19.02.2025 1:08:37
In today’s Casual Conversation, the hosts Deep Dive into today’s DL man and why they are still a thing. Oaklyn Jonas opens a discussion on the aesthetic of the modern DL man and the shift from predominantly DL tops to DL bottoms. In this segment, they chat about Oaklyn’s dive into dating post divorce and speaks on the change from the types of DL men he attracted pre and post marriage, open the flo...
Music N Memories 05.02.2025 1:05:27
Thank you for joining the the Conversation! In our first sit down on the Casually Deep podcast, Ressie G and OJ the OG welcome into their safe space and invite you to join their special group chat. In this episode, the hosts will discuss the world’s universal language, Music! They debate over the question of music transcending time. Open discussion on reality stars making music and the people they...
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