Skip to main content
Shoulda! Coulda! Woulda!

Shoulda! Coulda! Woulda!

By Dwight Allen ONeal

Have you ever wondered "What SHOULD have?" "What COULD have?" or "What WOULD have happened?" if you knew certain things before attempting or actually doing something? Well you can learn from me and my guests as we walk down memory lane on some of our biggest accomplishments and major life mistakes. Send your own "SCW Moment" or a comment to: YouShouldaCouldaWoulda@gmail.com Support Me: Become a Patron!
Available on
Google Podcasts Logo
Overcast Logo
Pocket Casts Logo
RadioPublic Logo
Spotify Logo
Currently playing episode

Split the Check (Bill)

Shoulda! Coulda! Woulda! May 19, 2021

00:00
38:42
Chose Motivation over Procrastination

Chose Motivation over Procrastination

Why do I keep putting things off?! I knew I should have ordered those shoes sooner. Why am I still working on this project. So many times I should have chosen motivation over procrastination. Well now we will unpack how to procrastinate no more (or try not to), and what it looks like to motivate ourselves.
Aug 24, 202227:08
Blocked My Blessings

Blocked My Blessings

Have you been there? Preventing yourself from receiving what is meant for you? Instead of going after the blessings God has prepared for us, sometimes we keep pursuing those things not meant for us. Join me as I share 12 tips on how to “unblock” your blessings.
Aug 17, 202231:14
August 17, 2022

August 17, 2022

Aug 17, 202200:58
Wait on God

Wait on God

How many times have you made God laugh? By telling him your plan. My recent life lesson was seeing that I things have shifted in my life from waiting on him. I also chat about God sending the right people into your life as you continue to radiate your greatness. In the words of Jenifer Lewis. “Get you an astronaut!”
Jul 20, 202233:20
Work Bestie

Work Bestie

Your work bestie is the one you spend all your breaks with and get into trouble with too. Going to work can be boring, unless you have a work bestie. Whether or not you admit it, and no matter how much of a boss you might be when it comes to work, everyone needs someone to chat with and more importantly, have your back at the 9-5.
Jul 06, 202234:47
Sneaky Link

Sneaky Link

Well now the kids out here nicknaming they side pieces sneaky links. Have you ever had one? Or is it not your thing. Well today I break down the do’s and don’ts of your sneaky link.
Jun 29, 202233:14
Superstitiously Me

Superstitiously Me

Have you heard that you shouldn’t step on a crack? Or do you fear Friday the 13th? A a widely held but unjustified belief in supernatural causation leading to certain consequences of an action or event, or a practice based on such a belief, is a superstition. Whether you admit to it or not, I am sure you believe in them. But what are their origins… let’s discuss!
Jun 22, 202229:11
Friend Zone

Friend Zone

Is there a such thing as the Friend Zone? The Friend Zone is a situation in which a friendship exists between two people, one of whom has an unreciprocated romantic or sexual interest in the other. Who puts the friend in the zone? And if you get in the zone how do you get out? We dive into that zone today!
Jun 15, 202234:04
Giving them their Flowers

Giving them their Flowers

While flowers are widely given, it is a form of expression that shows the people in your life that you love, appreciate, honor and cherish them while they're still living. For the most part, we all desire human connection and to make a meaningful impact on the lives of others. Today I reflect on a moment I wittiness flowers being delivered at someone’s funeral vs given to them….
Jun 08, 202230:15
Real-life Fairytale!

Real-life Fairytale!

In this EPISODE I discuss real-life fairytales. Think of people that you see who are living incredible lives that they have created. How did they create these wonderful lives? In life we create the life that we want and don’t forget it.
Jun 01, 202230:43
Charming A**hole

Charming A**hole

Everyone has a type. Or do they? Sometimes the type of person we date is based off of the trauma that we are attracting. On today’s episode we discuss the charming a**hole! Are they really your type? Or are you still healing?
May 25, 202237:00
No Season Finale

No Season Finale

So we kinda missed our Season 2 finale. You know life got the best of me. But some of our favorite tv shows, movies, books, or experiences didn’t really have a finale. Lets chat about what happened (Jussie Smollett Trial) and laugh our way into Season 3.
May 25, 202231:58
Fight for Your Fairytale

Fight for Your Fairytale

In this EPISODE of Shoulda! Coulda! Woulda! We put a stop to finding a Happy Ending, but learning to Fight for Your Fairytale.
Sep 08, 202131:27
Forgiveness

Forgiveness

In this EPISODE of Shoulda! Coulda! Woulda! Do you easily forgive? Do you forgive or forget? Is there anyone you need to forgive? Learn the 7 steps I have had to learn to forgive my ex and how I’m still working on forgiving a parent and how that parent needs to forgive me.
Sep 01, 202136:37
Spirit Air (ULCC Airline)

Spirit Air (ULCC Airline)

In this EPISODE of Shoulda! Coulda! Woulda! I talk about Spirit Airlines! Have you ever flown Spirit? Well if you have it you definitely wanna listen to this episode, but if you have this episode too. From charges on everything. Canceled flights AND SOOO MUCH MORE.
Aug 11, 202131:42
The "K" Response (Text Etiquette)

The "K" Response (Text Etiquette)

In this EPISODE of Shoulda! Coulda! Woulda! I talk about texting "K" in text messages. When is it rude, polite, or given way too much thought? We also dive into proper text message etiquette in general. SPECIAL ANNOUNCEMENT Collar Confessions The Series coming soon on HERE TV www.HERETV.com! Subscribe to HERE TV today and ORDER THE NEW BOOK: Collar Confessions (www.ONealAppeal.com/shop)

Aug 04, 202139:26
Urban Social Status

Urban Social Status

In this EPISODE of Shoulda! Coulda! Woulda! I talk about URBAN SOCIAL STATUS. Are you a hood rat ghetto bunny? Clatchet? Sadity? Hood? Well, today I unpack and explore with the handy "Urban Dictionary." SPECIAL ANNOUNCEMENT Collar Confessions The Series coming soon on HERE TV www.HERETV.com! Subscribe to HERE TV today and ORDER THE NEW BOOK: Collar Confessions (www.ONealAppeal.com/shop)

Jul 28, 202139:09
DL vs Trade

DL vs Trade

In this EPISODE of Shoulda! Coulda! Woulda! I talk DL vs TRADE. What is the difference?  Are some of these men thinking they are TRADE when they are TRISH??? Also what about gay curious, bi-curious, or event BOTTOM curious .... SPECIAL ANNOUNCEMENT Collar Confessions The Series coming soon on HERE TV www.HERETV.com! Subscribe to HERE TV today and ORDER THE NEW BOOK: Collar Confessions (www.ONealAppeal.com/shop)

Jul 21, 202142:00
Disrespectful Side-Piece

Disrespectful Side-Piece

In this EPISODE of Shoulda! Coulda! Woulda! I talk The disrespectful side piece. And I share tips on how the side piece and side chicks can actually thrive.... SPECIAL ANNOUNCEMENT Collar Confessions The Series coming soon on HERE TV www.HERETV.com! ORDER THE NEW BOOK: Collar Confessions (www.ONealAppeal.com/shop)
Jul 14, 202133:54
Royalty

Royalty

In this EPISODE of Shoulda! Coulda! Woulda! I talk about the Royal Family and the fact that WE (USA) Don't have one. I also name a few peeps in the USA who would make a incredible royalty... SPECIAL ANNOUNCEMENT Collar Confessions The Series coming soon! ORDER THE NEW BOOK: Collar Confessions (www.ONealAppeal.com/shop)
Jul 07, 202134:22
Sexting Nudies

Sexting Nudies

In this EPISODE of Shoulda! Coulda! Woulda! I discuss SEXTING... or sending XXX images. Is this appropriate? Or Not? Who does it more Men or Women? Also, we chat about a Shoulda! Coulda! Woulda... Titanic moment. Preorder my book "Collar Confessions" on Amazon.com and visit my website www.OnealAppeal.com for more info.

Jun 30, 202125:27
Shoot your Shot
Jun 23, 202136:52
Happy Pride
Jun 16, 202130:55
Battle of the Sexes (Masculine vs Feminine)

Battle of the Sexes (Masculine vs Feminine)

In this EPISODE of Shoulda! Coulda! Woulda! I bring on my sister Awaka and my good friend The Master Oracle (https://www.instagram.com/themasteroracle/). We discuss BATTLE OF THE SEXES... Masc vs Fem... Flirting and Being Flirted with. Do Prince Charming still exist? What do you consider an innapportiate way to approach a love interest in public? Be sure to visit my website to pre-order my new book: Collar Confessions (www.ONealAppeal.com/shop)
Jun 09, 202139:54
Revenge of the Villains

Revenge of the Villains

In this EPISODE of Shoulda! Coulda! Woulda! I talk about getting revenge... Spoiler Alert I do talk a little about Disney's Cruella, but not in a way that will ruin it for you. Take a listen and learn the best way to seek your own revenge. Also find out healthy revenge tactics. Be sure to visit my website to pre-order my new book: Collar Confessions (www.ONealAppeal.com/shop)
Jun 02, 202130:19
Worn A Diaper

Worn A Diaper

In this EPISODE of Shoulda! Coulda! Woulda! I talk about moments grown folks needed a diaper. Have you ever spent the night at someone's house and NOT know where the bathroom was... so you kinda had an accident? Ohhh Only just me??? And yes I was drunk (insert shame face). I also have a very special guest with me today.... My good judy Flash! Be sure to visit my website to pre-order my new book: Collar Confessions (www.ONealAppeal.com/shop)
May 26, 202134:58
Split the Check (Bill)

Split the Check (Bill)

In this EPISODE of Shoulda! Coulda! Woulda! I talk about dining out, and splitting the check. How often have you gone to or even hosted a celebratory dinner only to have that akward moment when the check arrives? We all know it... we have all experienced it at least once. Well who is wrong? Is it the person for picking the expensive eatery? Or the person who didn't have the coin to dine? Or perhaps even the person who only had water? You don't want to miss this! I also have a very special guest... Be sure to visit my website to pre-order my new book: Collar Confessions (www.ONealAppeal.com/shop)
May 19, 202138:42
Dated My Friends Ex!

Dated My Friends Ex!

In this EPISODE of Shoulda! Coulda! Woulda! I talk about Dating My Friends Ex: Yes I am trifling I know... but I can explain! With all this chatter around RHOA Star Porsha Williams new fiance, why not air my own dirty laundry. I also get my hatters together on my extended show break. I AM BACK! And excited to have you listen... I dropped this episode on you like Beyonce drops albums.
Be sure to visit my website to pre-order my new book: Collar Confessions (www.ONealAppeal.com/shop)
May 12, 202124:59
Summer Vacay with Covid-19

Summer Vacay with Covid-19

In the SEASON FINALE of Shoulda! Coulda! Woulda! I talk about going on vacay during Covid:19!! I also offer suggestions on ways to get some R&R during the pandemic. Order my book "Shoulda! Coulda! Woulda on Amazon.com and Visit my website www.OnealAppeal.com for more info.
Jun 24, 202037:22
Choose Between the Two

Choose Between the Two

In this EPISODE of Shoulda! Coulda! Woulda! I talk about choosing between two dates. We have all been seeing two men (or women) and you have to make a choice. How do you decide? Find out in this episode.
Jun 18, 202037:40
Me As A Child

Me As A Child

In this EPISODE of Shoulda! Coulda! Woulda! I talk about my childhood and coming to terms with being gay. I discuss playing college vs house, my first love, and my imaginary friend Sheila. Warning I do get a bit emotional.
Jun 10, 202037:00
Black Lives Matter

Black Lives Matter

In this short EPISODE of Shoulda! Coulda! Woulda! I get real about Black Lives Matter! Why does everyone care now? What more could I have done? What about black queer lives? Do companies really care? Let's get real with each other... WE ALL NEED TO STAND!
Jun 03, 202010:59
Kept My Keys
May 27, 202044:18
Cut Off Fake Friends
May 20, 202042:07
Barbershop vs Locker Room
May 13, 202037:06
Wrote a Book
May 06, 202029:05
Been a Celebrity
Apr 29, 202038:20
Umm... Netflix and Chillax
Apr 22, 202035:35
Dated Men!
Apr 15, 202039:49
Been on Reality TV
Apr 08, 202033:18
Yes! My a** Drunk (SMH)
Apr 01, 202036:56
Coronavirus is REAL!

Coronavirus is REAL!

In this EPISODE of Shoulda! Coulda! Woulda! we talk about "Coronavirus is REAL". I REALLY didn't want to discuss this pandemic, however it is the reality of the world. So because I love my listeners I want to empower you... The reality of it is... most likely you have to be home... And there are things you can do to make your situation better... let's explore those opportunities together. Also find out about my new reality show that I'm a cast member on... What better time to watch a new series that delivers drama.
Mar 25, 202037:09
Vacation with Friends!

Vacation with Friends!

In this EPISODE of Shoulda! Coulda! Woulda! we explore taking "Vacations with Friends". Chiillleee, talk about a risk! I love a great vacation and in the spirit of Spring Break what better time to discuss taking a little turn up trip with your crew?!
Learn some amazing tips planning, questions you should ask prior to planning, and some other fun stuff to plan the best trip! We all love to travel but vacation planning can make or break up a friendship....
Mar 25, 202046:05
Eat My Groceries

Eat My Groceries

In this EPISODE of Shoulda! Coulda! Woulda! we explore grocery shopping (or lack of grocery shopping). Grocery shopping is something my fridge never experiences, however I am trying to do better at the task.
Learn some amazing tips, proper grocery store etiquette, and some other fun stuff to keep your fridge stocked.
Mar 11, 202024:20
Yes! I left My JOB!

Yes! I left My JOB!

In THE THIRD EPISODE of Shoulda! Coulda! Woulda! I let the cat out of the bag! I quit my last job of only 6 months. I chat about reasons people leave jobs, when do you know it's time, and what to do???
You don't want to miss this!!! NOTE: This episode in no way bashes any establishment I have worked, however speaks to when it's time to move on.
Mar 04, 202028:09
I LOVE NYC?

I LOVE NYC?

In THE SECOND FIRST EPISODE of Shoulda! Coulda! Woulda! we explore my life in New York City... But most just say NYC!
I walk down memory lane as I move to a new city and started a brand new life. So many SWC moments... but I share my favorite 9 lessons. Listen, learn, and share yours too!
Feb 26, 202028:33
My Housekeeper found my "insert eggplant emoji"

My Housekeeper found my "insert eggplant emoji"

In THE FIRST EPISODE of Shoulda! Coulda! Woulda! we explore having a housekeeper and what to do when she finds your (insert eggplant emoji)... DILDO!!!
Also some great tips for hiring, managing, and maintaining an excellent housekeeper... Please don't judge me AND I hope my housekeepers comes back--- LOL
Feb 19, 202021:35