
Carefully Reckless
219 episodes — Page 4 of 5

S2 Ep 17Single for the Summer
Who is peeing in the dating pool?? In this episode, Jess is fixing a whole bunch of relationship mess. These situations are crazy, but at least now we know we're not the only ones going through some nonsense!See omnystudio.com/listener for privacy information.

S2 Ep 16Back to You
Hey yawwwwl, what's up? Jess was busy buying estates last week, but this week she's BACK and fixing your mess! Let's get into itSee omnystudio.com/listener for privacy information.

S2 Ep 15New Love
If you've been listening for a while, you might remember Jess' sister heartbreak story earlier in the season. Welp ..she's BACK giving us an update on her love life! See omnystudio.com/listener for privacy information.

S2 Ep 14Do You Boo Boo
What's the tea y'all? Jess is back again fixing your problems. We all have crazy situations, listen to Jess' advice on how to handle them. Tired of just listening and want Jess' opinion on YOUR situation? DM your questions to Jess on IG: @CarefullyRecklessPodcast See omnystudio.com/listener for privacy information.

S2 Ep 13Communication is Key
Jess is back with another full episode of Jess, Fix My Mess - answering questions about YOUR crazy life situations! Tap in!See omnystudio.com/listener for privacy information.

S2 Ep 12Jess, Fix My Mess!
If you've been rocking with Carefully Reckless since Season 1, then you're familiar with the "Jess, Fix My Mess" segment. Well Jess is bringing it BYKE for a whole episode! Jess is getting into y'all business for a whole 20 minutes ...but it's only 'cause you asked!See omnystudio.com/listener for privacy information.

S2 Ep 11Real Talk
Jess is reading y'all to filth for your reactions to the death of Kevin Samuels. She also gets into being one of the new couples on Couples Retreat. See omnystudio.com/listener for privacy information.

S2 Ep 10Dear Mama
Fresh off of Mother's Day weekend, Jess is showing love to all the mommas!See omnystudio.com/listener for privacy information.

S2 Ep 9How Close Is Too Close?
We finally got big London in the building!!! Jess and London talk about the boundaries of their relationshipSee omnystudio.com/listener for privacy information.

S2 Ep 8Bye Bus Driver
Jess is taking the back seat and letting her sister share the story about her recent heartbreak. If you're trying to keep a positive outlook on men ...this ain't the episode for you baby.See omnystudio.com/listener for privacy information.

S2 Ep 721 Questions - Deal or No Deal?
EJess has some questions about what love looks like and what you're willing to deal with. This episode will definitely give you some guidelines on experiencing different love languages. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

S2 Ep 6Heartbreak Kid
EJess is opening up about a recent incident with her father that has her feeling emotional. If you're a daddy's girl, get your tissues before you tap in! Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

S2 Ep 5Pursuit of Slappyness
EEveryone is talking about Will Smith smacking the taste out of Chris Rock's mouth so you know your girl Jess had to give her take on the situation! Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

S2 Ep 4Aye, Can We Get Trump Back?
EWtf is going on in America? Jess is giving her take on COVID and war! Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

S2 Ep 3I'm an "Extra"vert
EJess opens up about raising an introverted child. If you love an introvert, let Jess school you on how to handle them. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

S2 Ep 2Safe Travels!
EThis week Jess is coming to us straight out of Cabo and she has something heavy to share. Ladies, plan who you're going on trips with wisely! Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

S2 Ep 1Prison Bae
EAnd we byke!! Jess is back for another season, and she brought her sister Shay with her to kick things off. They're giving the tea on how a friendship with a facility inmate went left! Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

S1 Ep 51Carefully Reckless Replay - Protect Black Men
bonusEIt's the last Wednesday in Black History Month, so Carefully Reckless presents a replay of one of its most memorable episodes.Calling all black men! This is a safe place for you. Black women, I hope you're ready to take some accountability as Jess gives her opinion on the controversial topic of male vulnerability in the black community. Let's talk, so we can heal! Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

S1 Ep 50Carefully Reckless Replay - Forever Fiancee
bonusEStill feeling the spirit of love from Valentine's Day? Carefully Reckless presents a replay of one of its most memorable episodes.Ladies, does your man have a deadline to propose to you? Guys, is the pressure to get married a turn off? Tune in to hear what Jess and some of her fans had to say about the topic! Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Lessons Learned, Past & Present
Jess talks about a recent public incident, Euphoria and Regina King. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Jess & Rome Get Real
Jess and Rome talk about their past and present relationship, Ashton and co-parenting. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Ashton Is Back!
Jess and her son Ashton talk about Covid, the holidays, school and much more! Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

What Turns You On?
Jess and her family talk about all things sex, including stimulation, condoms, and threesomes. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Dating For Today
Jess and her crazy family share dating stories and talk about relationships. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Blood Is Thicker Than Water
Jess takes Shay down memory lane to talk about a dramatic breakup with an ex. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Put Ya Money Where Your Mouth Is
Jess and Shay talk about Black-owned businesses. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Meet Ash Hilarious!
Jess sits down with her son Ashton to talk about comedy, family, football and the future. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

Vaccine Views
Jess and Tanya (@itsgreat2bme) talk about Covid-19 and vaccines. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

The Astroworld Festival Tragedy
Jess gives her raw reaction to the tragedy at Travis Scott's Astroworld Festival, which resulted in eight deaths. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

S1 Ep 39Why You So Obsessed with Me?
EJess taps into a real creepy topic right in time for Halloween! We're getting into dangerous obsessions. Lock your doors and check your surroundings before you tune into this one! Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

S1 Ep 38I Don't Owe You Sh*t
EJess opens up and gives us some raw emotion this week. Sometimes when your friends got you f*cked up, you gotta vent to your fans. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

S1 Ep 37Pride Will Be Your Downfall
ELearn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

S1 Ep 36Mirror Mirror on the Wall
EJess and Shay get real about an issue that many people in this era struggle with - Body Dysmorphia Disorder (BDD). Baby, social media got us tweakin'! You're beautiful the way you are ...but get into this episode. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

S1 Ep 35You Pregnant Teww?
ENow y'all know it be the most raggedy men who wanna play games! Shay is back and sharing some trifling stories with Jess ☕️ Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

S1 Ep 34Were You Born Like That?
EJess introduces us to a new guest and they're checking y'all on something other people might be too afraid to ...your weight! Put that burger down and turn the volume up. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

S1 Ep 3321 Questions
ESheena Girl is BIKE again!!! Jess is asking a bunch of rapid fire questions - are y'all ready for these answers? Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

S1 Ep 32I Do! Wait, You Don't?
EDid you ever have to say no to a marriage proposal? Was it justified? Did the relationship end after that? Let's talk! Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

S1 Ep 31Tell Me Your Fantasy
EJess is bringing one of her life lessons into story time. Do you tell your boo about your fantasies with other people? Neither does Jess ...well except for that one time! Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

S1 Ep 30Either You Is or You Ain't
EIf you have one relationship with the same sex, does that mean you're gay? Jess invites Prince back to talk about the double standards of sexuality. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

S1 Ep 29Stay Trippin'
EJess' twin pulled up for this week's episode! Jess and Prince recap the highs and lows of their traveling experiences. Expect some drama, personality breakdowns and baecations! Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

S1 Ep 28What Department Are You In?
ESheena Girl is BIKE ..you'll get it when you listen to the episode. Anyway, they're breaking down LGBTQIA+ the Carefully Reckless way. Y'all please don't start a cancel campaign after this!! Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

S1 Ep 27Bmore Besties
EWho else gets jealous when their bestie has other friends? Well, Jess' REAL best friend, Sheena Girl, hopped on this episode to press Jess about her other "best friends". Spoiler Alert: Sheena also reveals a secret about Jess that you don't want to miss! Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

S1 Ep 26Get Your Friend!
EBria is back by popular demand! This time the ladies are discussing friendship boundaries. Can your friend check your man? Can you check your friend? Let's find out what Jess and Bria think Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

S1 Ep 25I'm Coming to You As a Woman
EJess is back with more girl talk with her homegirl Bria! How do you feel about the "coming to you as a woman" concept? Well, Jess and Bria are giving their take and spilling some personal tea in the process!! Whew. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

S1 Ep 24Real & Raw
EWe already feel like Jess is our homegirl, but today she makes it real! In the middle of moving, Jess and her friend Bria got into some girl talk that everyone can relate to, so Jess plugged in the mics and got to recording! Tune in to this raw, unedited conversation that we've all had at least once in our lives. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

S1 Ep 23COVID Continues
EWhile everyone is taking off their masks and hitting these streets ... Jess is here to remind you that COVID-19 still exists. Stay safe and don't let this sickness catch you slippin!! Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

S1 Ep 22Buy Black
EJess is covering all sides of a major topic in the black community - supporting black business. Jess wants to see all her people win, even if that means calling out business owners AND consumers! Get into it Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

S1 Ep 21Who's Your Daddy?
EWhat's the difference between a father and a dad? While we're getting ready to celebrate Father's Day, Jess is showing love to all the DADs! Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

S1 Ep 20Can I Get A Refund?
EJess talks about how the power of social media tricked all of our asses into thinking that Floyd Mayweather vs. Logan Paul was an actual fight. Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.

S1 Ep 19Match My Fly or Bye Bye Bye
EVENT SESSION! Jess drops the usual structure of the show to speak her mind on a controversial topic. What's wrong with a woman wanting a man with money?? Nothing! And Jess is about to explain exactly why. Get into it! Learn more about your ad-choices at https://www.iheartpodcastnetwork.comSee omnystudio.com/listener for privacy information.