• Ep 93: Starting Scared
    Dec 18 2025

    Send us a text

    Support the show

    IG: @CupOfConversation_
    Facebook: CupOf Conversation
    YouTube: Cup Of Conversation w/ Coco & Tee
    Tiktok: CupOfConversation


    Follow Coco:
    https://www.instagram.com/chitchatcoco/
    Follow Tee:
    https://www.instagram.com/teeboss_/

    !!!LIKE SUBSCRIBE COMMENT!!!

    Suggest juicy controversial topics for Tee's topics, DM us on IG Or voice some of your concerns with Coco. Tell us some things that bother you these days or things you notice about our communities by simply shoot us a DM on IG!


    !!!LIKE SUBSCRIBE COMMENT!!!

    Show More Show Less
    26 mins
  • Ep 92 | Mindset, Opportunities & The Reality of the Grind
    Dec 11 2025

    Send us a text

    What’s up, Sippers! ☕️
    Welcome back to another cup of conversation — where we have conversations worth having. Today, Tee & Coco are diving deep into Episode 92 (yes, we finally got the number right this time 😂). We’re inching closer to 100, and the vibes are only getting better!

    In this episode, we cover:

    🔥 Thanksgiving highs, family chaos, and fasts that test your discipline
    🔥 Growing up with different mindsets — 9–5 households vs. entrepreneurial parents
    🔥Do we *really* all have the same opportunities?
    🔥 Is “striving” always healthy or is it just the American rat race talking?
    🔥 Why expectations, mindset, and reality don’t always align
    🔥 What happens when life derails your plan — and how the journey reshapes your purpose
    🔥 Honoring people who *can’t* afford to sit still, even when we talk “rest”

    PLUS:
    ➡️ Our new segment “What I Said Was" — where we clarify the things that don’t always come out right the first time.
    ➡️ Patreon family, we gave y’all some exclusive gems from last episode, so go check those out too!

    If you missed the Patreon-only clip that sparked *this* conversation, hit pause, head over there, and run it back. Patreon is **FREE** right now to join — grab it while you can!

    ---

    💬 Join the conversation:

    Do you think everyone is actually afforded the same opportunities?
    Is mindset enough?
    Or does circumstance win?

    Drop your thoughts in the comments — we want to hear from the Sipper community.

    ---

    📌 PATREON

    Exclusive content, extended convos & bonus episodes:
    👉 Join us on Patreon (free for now!)

    ---

    ✨ Don’t forget:

    👍 Like
    💬 Comment
    🔔 Subscribe
    …so you don’t miss Episode 100 coming up in February (Love Month + Black History Month — it’s about to be A TIME).

    Sip with us, learn with us, and grow with us. 💛
    — Tee & Coco

    ---

    If you want a shorter version, SEO-optimized version, or timestamps added, just let me know!

    Support the show

    IG: @CupOfConversation_
    Facebook: CupOf Conversation
    YouTube: Cup Of Conversation w/ Coco & Tee
    Tiktok: CupOfConversation


    Follow Coco:
    https://www.instagram.com/chitchatcoco/
    Follow Tee:
    https://www.instagram.com/teeboss_/

    !!!LIKE SUBSCRIBE COMMENT!!!

    Suggest juicy controversial topics for Tee's topics, DM us on IG Or voice some of your concerns with Coco. Tell us some things that bother you these days or things you notice about our communities by simply shoot us a DM on IG!


    !!!LIKE SUBSCRIBE COMMENT!!!

    Show More Show Less
    37 mins
  • EP 91: The Art of Compromise vs. The Trap of Settling
    Dec 5 2025

    Send us a text

    Are you *settling*… or just choosing peace? 👀

    In this week’s episode of *Cup of Conversation*, Coco & Tee are diving into what it really means to *settle* — in love, in life, and in your career. From funny stories about times we knew we were settling (but did it anyway 😅), to real talk about Ayesha Curry’s recent comments on her marriage, this episode blends laughs, honesty, and a few hard truths.

    We’re asking:
    ☕ Is settling the same as compromising?
    💔 When is it choosing stability over chaos?
    💼 Is chasing passion a privilege, or should everyone demand more from their work?

    Grab your cup and join the conversation — because sometimes, settling isn’t giving up… it’s growing up.

    👇🏾 Let us know in the comments: Would YOU rather settle for stability or risk it all for what you really want?

    Support the show

    IG: @CupOfConversation_
    Facebook: CupOf Conversation
    YouTube: Cup Of Conversation w/ Coco & Tee
    Tiktok: CupOfConversation


    Follow Coco:
    https://www.instagram.com/chitchatcoco/
    Follow Tee:
    https://www.instagram.com/teeboss_/

    !!!LIKE SUBSCRIBE COMMENT!!!

    Suggest juicy controversial topics for Tee's topics, DM us on IG Or voice some of your concerns with Coco. Tell us some things that bother you these days or things you notice about our communities by simply shoot us a DM on IG!


    !!!LIKE SUBSCRIBE COMMENT!!!

    Show More Show Less
    25 mins
  • Ep 90: Gratitude in the Middle of the Struggle
    Nov 28 2025

    Send us a text

    Welcome back to the Cup of Conversation Podcast — where the tea is hot, the laughs are loud, and the truth is never on sale.

    In this episode, we’re diving into holiday season in real life, not the Pinterest version. From grocery prices that feel like betrayal to gratitude that has to coexist with frustration, Coco & Tee are unpacking the emotional, financial, and cultural weight of Thanksgiving in 2025.

    We’re talking the government shutdown that threw families off for weeks, delayed SNAP benefits, and what it really looks like when households have to stretch, squeeze, and remix traditions just to make the holiday happen.
    Because listen… hosting a big Thanksgiving when groceries cost like luxury items? Whew.

    We’re asking the questions everybody’s whispering:
    Is the pressure to “host big” outdated or is that cultural pride still fighting for its life?
    Are we scaling down our menus or scaling up our sanity?
    Can you really be grateful and irritated at the same time, or is that just adulthood?
    Is survival mode a mindset or a season… and how do you practice gratitude in the middle of it?
    What’s one thing you’re thankful for this year that didn’t come with a price tag?

    And of course we had to get into the holiday weekend debates:
    Are you team “rest & recharge” or team “I’ll sleep in January” for Thanksgiving weekend?
    Is Black Friday even Black Friday anymore, or just a four-day hostage situation for our wallets?
    How do you stay generous without going broke?
    And who decided Thanksgiving needed a sequel… because Cyber Monday is wild.

    It’s honest, it’s relatable, and it’s giving “making it work with what you got” — because that’s where a lot of people really are.
    Grab your cup and pull up… it’s conversation time. ☕💬

    If you’re rocking with the episode, hit that like, comment, and subscribe button so you don’t miss the next one!

    Support the show

    IG: @CupOfConversation_
    Facebook: CupOf Conversation
    YouTube: Cup Of Conversation w/ Coco & Tee
    Tiktok: CupOfConversation


    Follow Coco:
    https://www.instagram.com/chitchatcoco/
    Follow Tee:
    https://www.instagram.com/teeboss_/

    !!!LIKE SUBSCRIBE COMMENT!!!

    Suggest juicy controversial topics for Tee's topics, DM us on IG Or voice some of your concerns with Coco. Tell us some things that bother you these days or things you notice about our communities by simply shoot us a DM on IG!


    !!!LIKE SUBSCRIBE COMMENT!!!

    Show More Show Less
    22 mins
  • EP 89: If Thanksgiving Had A Therapist...
    Nov 20 2025

    Send us a text

    Welcome back to the Cup of Conversation Podcast — where the tea is hot, the laughs are loud, and the truth is never on sale.

    In this episode, we’re diving into holiday season in real life, not the Pinterest version. From grocery prices that feel like betrayal to gratitude that has to coexist with frustration, Coco & Tee are unpacking the emotional, financial, and cultural weight of Thanksgiving in 2025.

    We’re talking the government shutdown that threw families off for weeks, delayed SNAP benefits, and what it really looks like when households have to stretch, squeeze, and remix traditions just to make the holiday happen.
    Because listen… hosting a big Thanksgiving when groceries cost like luxury items? Whew.

    We’re asking the questions everybody’s whispering:
    Is the pressure to “host big” outdated or is that cultural pride still fighting for its life?
    Are we scaling down our menus or scaling up our sanity?
    Can you really be grateful and irritated at the same time, or is that just adulthood?
    Is survival mode a mindset or a season… and how do you practice gratitude in the middle of it?
    What’s one thing you’re thankful for this year that didn’t come with a price tag?

    And of course we had to get into the holiday weekend debates:
    Are you team “rest & recharge” or team “I’ll sleep in January” for Thanksgiving weekend?
    Is Black Friday even Black Friday anymore, or just a four-day hostage situation for our wallets?
    How do you stay generous without going broke?
    And who decided Thanksgiving needed a sequel… because Cyber Monday is wild.

    It’s honest, it’s relatable, and it’s giving “making it work with what you got” — because that’s where a lot of people really are.
    Grab your cup and pull up… it’s conversation time. ☕💬

    If you’re rocking with the episode, hit that like, comment, and subscribe button so you don’t miss the next one!

    Support the show

    IG: @CupOfConversation_
    Facebook: CupOf Conversation
    YouTube: Cup Of Conversation w/ Coco & Tee
    Tiktok: CupOfConversation


    Follow Coco:
    https://www.instagram.com/chitchatcoco/
    Follow Tee:
    https://www.instagram.com/teeboss_/

    !!!LIKE SUBSCRIBE COMMENT!!!

    Suggest juicy controversial topics for Tee's topics, DM us on IG Or voice some of your concerns with Coco. Tell us some things that bother you these days or things you notice about our communities by simply shoot us a DM on IG!


    !!!LIKE SUBSCRIBE COMMENT!!!

    Show More Show Less
    28 mins
  • Ep. 88: Double Standards Reloaded
    Nov 13 2025

    Send us a text


    Why can he do it but she can’t?

    This week on Cup of Conversation, Coco & Tee are back on the couch updating the Double Standard List — because let’s be real, some of these old-school rules need to retire. From dating and money to gender roles and reputation, we’re breaking down the messy, funny, and sometimes uncomfortable truths about how men and women are judged differently.

    And of course, our producer Braxton jumps in to give the male perspective — so you already know things get interesting. 😏

    We’re unpacking:
    💸 What happens when the woman makes more in a relationship?
    💬 Why women are “bossy” but men are “leaders.”
    🔥 “Body count” honesty vs. privacy — does transparency help or hurt?
    🤝 Are double standards natural differences or learned mindsets?

    Plus, in The Last Sip, we’re putting these double standards to the test with a few wild “this or that” scenarios you won’t want to miss!

    👇🏾 Drop your thoughts in the comments:
    Which double standard are YOU tired of seeing play out?


    Follow & Subscribe:
    🎧 Listen on Spotify & Apple Podcasts: [insert links]
    📸 Follow us on Instagram: [@cupofconversationpod](#)
    💌 Join our Patreon for exclusive content & early access: [insert link]

    Support the show

    IG: @CupOfConversation_
    Facebook: CupOf Conversation
    YouTube: Cup Of Conversation w/ Coco & Tee
    Tiktok: CupOfConversation


    Follow Coco:
    https://www.instagram.com/chitchatcoco/
    Follow Tee:
    https://www.instagram.com/teeboss_/

    !!!LIKE SUBSCRIBE COMMENT!!!

    Suggest juicy controversial topics for Tee's topics, DM us on IG Or voice some of your concerns with Coco. Tell us some things that bother you these days or things you notice about our communities by simply shoot us a DM on IG!


    !!!LIKE SUBSCRIBE COMMENT!!!

    Show More Show Less
    30 mins
  • Episode 87: Is Love Enough? | The Real Conversation About Marriage Beyond the Aesthetic
    Nov 6 2025

    Send us a text

    Is Love Enough? | Marriage Beyond the Aesthetic | Cup of Conversation w/ Tiara & Josh
    Everyone loves the wedding photos—but what happens after the filters fade?This week, Tiara and Josh get brutally honest about the real work behind “forever.” From the ride-or-die myth to fighting for your marriage without losing yourself, we’re unpacking what it truly takes to stay in love when things get messy.
    ☕ In this episode:
    • The LeBron James quote that sparked a heated debate 🔥
    • “The Fight to Keep Mine” — when love turns into labor
    • Are Black couples redefining vulnerability or masking fear?
    • How to keep your identity while growing together
    • For Better or Petty—a game that exposes who’s really hanging up mid-argument 👀
    Join the conversation:Drop your thoughts in the comments — Is love enough, or does marriage take a whole new strategy?
    Subscribe for more unfiltered convos on love, culture, and growth.Hit that 🔔 so you don’t miss the next pour-over!
    #CupOfConversation #MarriageTalk #BlackLove #IsLoveEnough #RelationshipGoals #PodcastLife #RealTalk #LoveAndMarriage

    Support the show

    IG: @CupOfConversation_
    Facebook: CupOf Conversation
    YouTube: Cup Of Conversation w/ Coco & Tee
    Tiktok: CupOfConversation


    Follow Coco:
    https://www.instagram.com/chitchatcoco/
    Follow Tee:
    https://www.instagram.com/teeboss_/

    !!!LIKE SUBSCRIBE COMMENT!!!

    Suggest juicy controversial topics for Tee's topics, DM us on IG Or voice some of your concerns with Coco. Tell us some things that bother you these days or things you notice about our communities by simply shoot us a DM on IG!


    !!!LIKE SUBSCRIBE COMMENT!!!

    Show More Show Less
    28 mins
  • Ep 86: It’s Not Beef, I Just Outgrew You
    Nov 6 2025

    Send us a text


    This week on Cup of Conversation, we’re getting real about friendship — the good, the fake, and the fragile. From vulnerability to “it girl” culture, we’re unpacking what it really means to be a girlfriend in 2025.

    We start light with our “How You Feelin’, Friend?” check-in before diving into the deep stuff — how our moms shaped the way we view friendship, why women struggle with vulnerability, and if being in a different season of life means it’s time to let go.

    Our guest Oksana joins Coco & Tee as we ask the real questions:
    ✨ Are we truly being vulnerable with our friends or just performing closeness?
    ✨ Can you outgrow a friend without the beef?
    ✨ Is “protect your peace” just a cute excuse to dodge accountability?
    ✨ And why does being the “strong friend” so often mean no one shows up for you?

    Grab your cup and tap in — this one’s for every woman trying to redefine sisterhood in a world that rewards detachment.

    🎧 Available now on YouTube & Patreon
    #CupOfConversation #GirlfriendsTalk #FemaleFriendship #PodcastVibes

    Support the show

    IG: @CupOfConversation_
    Facebook: CupOf Conversation
    YouTube: Cup Of Conversation w/ Coco & Tee
    Tiktok: CupOfConversation


    Follow Coco:
    https://www.instagram.com/chitchatcoco/
    Follow Tee:
    https://www.instagram.com/teeboss_/

    !!!LIKE SUBSCRIBE COMMENT!!!

    Suggest juicy controversial topics for Tee's topics, DM us on IG Or voice some of your concerns with Coco. Tell us some things that bother you these days or things you notice about our communities by simply shoot us a DM on IG!


    !!!LIKE SUBSCRIBE COMMENT!!!

    Show More Show Less
    31 mins