Playing 4 Keeps

Send us Fan Mail

What happens when trying to help someone you're dating turns into a situation you never expected?

On this episode of Playing 4 Keeps, DJ sits down with RJ, a 61-year-old pharmacist and business owner who has learned more than a few lessons about dating, honesty, boundaries, and knowing when enough is enough.

RJ says lying is one of his biggest pet peeves, but DJ quickly puts that philosophy to the test after RJ admits he once told a lie of his own just to escape a bad date. That opens the door to a much bigger conversation about whether every lie is equal, the questions we should be asking before getting involved with someone, and whether people sometimes overlook warning signs because they want things to work.  Pasted text  Pasted text

Then RJ shares the dating experience that took things much further.

After dating a woman dealing with personal struggles, RJ eventually allowed her to move into his home. But as the relationship deteriorated, they began sleeping in separate rooms, tensions grew, and when he asked her to move out, her response was simple: she would leave when she wanted to.

That is when RJ called his attorney.

What followed was a lesson in boundaries, relationships, trying to save someone who may not want your help, and recognizing the part you play in the situations you repeatedly find yourself in.  Pasted text  Pasted text

DJ also challenges RJ on whether being a “nice guy” is really the reason he feels taken advantage of, what he could do differently in his next relationship, and what he is actually looking for in a partner today. RJ says his priorities now include honesty, kindness, respect, love, and a woman who puts God first.  Pasted text  Pasted text

Could you date someone after discovering they had been hiding major parts of their life? And how far should you go trying to help someone before you realize the relationship itself isn't working?

Watch the full conversation and tell us what you think in the comments.

Playing 4 Keeps
Dating is a mess... but we keep playing.

📲 Want to be featured on Playing 4 Keeps?
Visit playing4keepsdating.com/be-a-guest/

Follow us: @playing4keepsdating

Support the show

Dating is a mess, but we keep it moving. Want to be a guest on Playing 4 Keeps? Click Here to submit your application.

Produced by Organized Movements

Recorded at PriviCast Studio

Visit our Website playing4keepsdating.com

Send us Fan Mail

What happens when a first date starts off smooth, but one moment completely changes the energy?

On Episode 13 of Playing 4 Keeps, DJ sits down with Mark (@markwhereyouat) for a real conversation about reciprocity, dating with intention, first-date boundaries, and why dating is really a vetting process.

Mark shares a date that started with flowers, good conversation, and plans to keep the night going. But once they got to the next spot, another man entered the picture and Mark had to decide whether to react, walk away, or handle the situation differently.  

That story opens the door to a much bigger conversation about dating out of deprivation, knowing whether someone has a reciprocating spirit, how much vetting can actually happen before a first date, and whether people are truly showing up ready to share their lives with somebody else.  

Mark also gets specific about what he wants in a partner, from individuality and emotional steadiness to friendship, financial responsibility, softness, humor, and being genuinely partnership-minded. 

And then there’s the question that sits underneath the whole episode:

Are you really ready to date, or are you just looking for what you can get from somebody?

🎙️ Playing 4 Keeps | Episode 13
Guest: Mark
Instagram: @markwhereyouat

Dating is a mess, but we keep playing.

#Playing4Keeps #DatingPodcast #ModernDating #DatingStories #Relationships

Support the show

Dating is a mess, but we keep it moving. Want to be a guest on Playing 4 Keeps? Click Here to submit your application.

Produced by Organized Movements

Recorded at PriviCast Studio

Visit our Website playing4keepsdating.com

Send us Fan Mail

What would you do if your first date ended… and five minutes later, she called you from the side of the road?

On this episode of Playing 4 Keeps, DJ sits down with Mark for a conversation about dating, communication, ghosting, closure, compatibility — and a first date that went completely off the rails.

What started as a setup through a mutual friend quickly turned into a night Mark definitely wasn't expecting. The chemistry wasn't quite there, the differences started showing up fast, and they had already decided there probably wouldn't be a second date. 

Then came the phone call.

And somehow, Mark ended up bailing his first date out of jail. 

But that's not even the whole story.

DJ and Mark also get into whether no response is a response, why people pull back when effort isn't being reciprocated, and what happens when you stop trying to love hard enough for two people. 

And after hearing everything that happened, there's one question you have to answer:

Would YOU have bailed her out?

🎙️ Playing 4 Keeps
I Bailed Her Out of Jail on Our First Date | ft. Mark

Dating is a mess… but we keep playing.

Support the show

Dating is a mess, but we keep it moving. Want to be a guest on Playing 4 Keeps? Click Here to submit your application.

Produced by Organized Movements

Recorded at PriviCast Studio

Visit our Website playing4keepsdating.com

Send us Fan Mail

Dating is already hard enough. But what do you do when the red flags start showing up before the first date is even over? 😂

On Episode 11 of Playing 4 Keeps, DJ sits down with Cali (@justmecali) for a hilarious and very real conversation about online dating, first-date disasters, dating standards, boundaries, and knowing when it’s time to BLOCK and move on.

Cali shares one unforgettable date with a man who showed up straight from work, wanted to share her drink, wanted to share the food, and somehow thought the date was still going well. 😳 And that's only ONE of her dating stories.

But the conversation goes much deeper than bad dates.

Cali opens up about realizing she had a pattern of dating down, being a giver who attracted takers, and finally deciding that seeing the good in someone isn't enough if they don't meet the standards she's set for her life.

The conversation gets into:

Dating red flags and dealbreakers
Online dating and first-date expectations
Why women sometimes date below their standards
Being a giver and recognizing takers
Dating multiple people at the same time
The 90-day rule for deciding if someone is relationship material
Financial stability, careers, passports and living situations
Dating with intention without turning every date into a job interview
Knowing when someone genuinely likes YOU instead of what you can do for them

And the big question: Are your standards protecting your peace…or are you still giving the wrong people too much access?

Dating is a mess, but we keep playing.

🎙️ Playing 4 Keeps — Episode 11
Guest: Cali | @justmecali

Follow @playing4keepsdating for more real dating stories, relationship conversations, red flags, lessons learned and everything happening in modern dating.

Support the show

Dating is a mess, but we keep it moving. Want to be a guest on Playing 4 Keeps? Click Here to submit your application.

Produced by Organized Movements

Recorded at PriviCast Studio

Visit our Website playing4keepsdating.com

Send us Fan Mail

What happens when a date is going perfectly... until her baby daddy shows up at 3 o’clock in the morning?

This week on Playing 4 Keeps, DJ sits down with Aaron Galloway for a dating story that goes from promising to potentially dangerous very quickly.

After meeting a woman and immediately hitting it off, Aaron thought he might have found something real. Within weeks, he was meeting family, spending time at her home and getting pulled deeper into her life. Then her children’s father showed up. What happened next left Aaron wondering why he had ignored the warning signs and taught him one very specific dating lesson: know what you’re walking into before somebody else’s unresolved relationship becomes your problem.  

But this conversation goes much further than one crazy date.

DJ and Aaron get into dating red flags, moving too fast, love bombing, trying too hard to prove you’re relationship material, dating as a single parent, sex too early, successful men with too many options, dating in Atlanta, and why you have to listen when someone tells you they don’t want a relationship.

Aaron also challenges women to stop dating based on who they think a man could become. If he tells you he does not want a relationship, believe what he is telling you instead of trying to convince him to want one. 

And when it comes to getting physical too quickly, Aaron has another warning: if sex is the main thing on his mind, he may not be looking for a wife at all. 

Dating is a mess, but we keep it moving.

Subscribe to Playing 4 Keeps for real dating stories, relationship conversations, lessons learned and the kind of dating advice that comes from actually living through it.

Topics: dating red flags, modern dating, dating in Atlanta, relationships, baby daddy drama, love bombing, dating advice for women, single parents dating, situationships, moving too fast, relationship advice

#Playing4Keeps #DatingRedFlags #ModernDating #DatingAdvice #Relationships

Support the show

Dating is a mess, but we keep it moving. Want to be a guest on Playing 4 Keeps? Click Here to submit your application.

Produced by Organized Movements

Recorded at PriviCast Studio

Visit our Website playing4keepsdating.com

Send us Fan Mail

Ric Holcomb Jr. comes to Playing 4 Keeps with a dating rule that is guaranteed to start a conversation: don’t date baddies.

Ric says some of his worst dating experiences came from the women he considered the most attractive. From constantly dealing with other men approaching his partners to jealousy, material expectations, and relationships becoming more complicated as attention increased, Ric explains why he believes dating a “10” can come with more than just good looks. DJ challenges that theory and asks whether the real issue is beauty or simply choosing the wrong type of woman.  

Then Ric tells the story of a date that went completely left. She told him she only went to expensive restaurants, barely held a conversation once they got there, sent her food back twice, and left Ric wondering why he had agreed to the date in the first place. His solution? Put money on the table and leave.  

The conversation also gets into male jealousy, dating someone with “motion,” independence, money, faith, intelligence, and what Ric says a woman needs to bring to the table if she wants to date him today.  

Guest: Ric Holcomb Jr.
Instagram: @ricmystroholcombjr

Subscribe to Playing 4 Keeps for dating stories, relationship debates, red flags, lessons learned, and conversations about what modern dating really looks like.

Support the show

Dating is a mess, but we keep it moving. Want to be a guest on Playing 4 Keeps? Click Here to submit your application.

Produced by Organized Movements

Recorded at PriviCast Studio

Visit our Website playing4keepsdating.com

Send us Fan Mail

On this episode of Playing 4 Keeps, Ms. Tee joins DJ for a candid conversation about toxic dating cycles, inconsistency, grief, overgiving, and finally learning when enough is enough.

Ms. Tee opens up about a nearly decade-long on-and-off connection with a man who eventually got married—on her birthday—only to circle back into her life later. When they finally had the opportunity to seriously explore a relationship, the same inconsistency and disappointment resurfaced.
She also reflects on losing a longtime partner, how grief changed the way she approaches relationships, and why she refuses to spend another decade caught in a runner-chaser dynamic. At 41, Ms. Tee says her tolerance for games, dishonesty, and mixed signals is gone. If you don't make your intentions clear, she's getting off the exit.

The conversation gets even deeper as DJ and Ms. Tee unpack what happens when you're naturally a giver but realize you've been pouring too much into people who aren't matching your effort. Ms. Tee talks about no longer wanting to date “projects,” wanting a man who is intentional, values her time, and can grow with her instead of expecting her to fix, motivate, or carry him.

From dating in Atlanta to whether you're really “single until you're married,” this episode is about breaking old patterns, protecting your time, and figuring out how to receive the love you want without returning to the habits that drained you in the first place.

Playing 4 Keeps — where dating is a mess, but we keep it moving.

Support the show

Dating is a mess, but we keep it moving. Want to be a guest on Playing 4 Keeps? Click Here to submit your application.

Produced by Organized Movements

Recorded at PriviCast Studio

Visit our Website playing4keepsdating.com

Send us Fan Mail

What happens when dating expectations, culture, masculinity, money, and identity all collide?

This week on Playing 4 Keeps, DJ sits down with Vigilante (@vigilantelom) for a conversation that challenges some of the most common ideas about modern relationships. From entitlement and reciprocity to traditional roles, family influence, and what we should actually be looking for in a partner, Vigilante has some strong opinions—and DJ isn’t letting any of them slide without a little pushback.

The conversation gets provocative, uncomfortable, and surprisingly personal as they unpack how the lives we build, the things we believe, and even where we come from can shape the way we love.

And when Vigilante shares one of his wildest dating experiences, the conversation around who should pay takes a whole different turn.

This is definitely one of those episodes where you’ll pick a side.

Follow Vigilante on Instagram: @vigilantelom

Support the show

Dating is a mess, but we keep it moving. Want to be a guest on Playing 4 Keeps? Click Here to submit your application.

Produced by Organized Movements

Recorded at PriviCast Studio

Visit our Website playing4keepsdating.com

Send us Fan Mail

What happens when you spend nearly $200 on a first date, only to hear, “I don’t see a romantic connection”?

On this episode of Playing 4 Keeps, DJ sits down with Sean Garvey for a conversation about dating expectations, rejection, money, accountability, and what men and women really owe each other after a date.

Sean shares the story of taking a woman out, covering the entire bill, and later jokingly asking for his money back after she told him she wasn’t interested. He also opens up about how his perspective has changed since then, why he now believes some dating lessons simply come with a cost, and how getting to know someone before rushing into a date can save time, money, and disappointment. 

But the conversation does not stop there. Sean gets personal about a past relationship that pushed him outside of his comfort zone, challenged how he saw himself, and led to unexpected experiences around intimacy, identity, and personal growth. He and DJ also unpack the difference between being challenged in a relationship and losing yourself trying to become what someone else wants.  

And when it comes to what Sean wants now, he makes one thing clear: he is not interested in dating just for the experience anymore. He is looking to build with someone who is healed, intentional, open-minded, and ready for something real. 

Follow Sean on Instagram: @seangarveyatl

Support the show

Dating is a mess, but we keep it moving. Want to be a guest on Playing 4 Keeps? Click Here to submit your application.

Produced by Organized Movements

Recorded at PriviCast Studio

Visit our Website playing4keepsdating.com

Send us Fan Mail

Cayla is dating with one goal in mind: finding a husband. She knows her non-negotiables, values consistency, and is not afraid to walk away when something does not align.

But one first date tested everything. What started as drinks, dinner, and a strong connection quickly turned into jealousy, an unnecessary confrontation, and a fight that nearly sent her date over a second-floor balcony.

Cayla joins DJ to talk about recognizing insecurity early, knowing the difference between reacting from trauma and learning from it, practicing abstinence while dating, and why she is finally open to trying a more intentional dating app.

Follow Cayla on Instagram at @thecayladee.

Crazy stories. Real love. Let’s get into it.

Support the show

Dating is a mess, but we keep it moving. Want to be a guest on Playing 4 Keeps? Click Here to submit your application.

Produced by Organized Movements

Recorded at PriviCast Studio

Visit our Website playing4keepsdating.com