I AM TRYING 2 HAVE A CONVERSATION WITH YOU

About I AM TRYING 2 HAVE A CONVERSATION WITH YOU

I’m Trying to Have a Conversation with You is a weekly podcast hosted by sisters Monique and Kasha, whose nearly 12-year age gap somehow turned into their greatest strength. What started as lifelong, constantly interrupted phone calls has become a space for honest, funny, and thoughtful conversations about life as women, mothers, sisters, and humans trying to make sense of the world. From motherhood and mental health to relationships, pop culture, work, grief, joy, and the ridiculous things we all deal with, no topic is off limits—and no conversation has to end in agreement. With humor, mutual respect, and a lot of lived experience, Monique and Kasha bring two generational perspectives to the table, proving that meaningful conversations can happen even when opinions differ. Expect laughs, vulnerability, strong takes, and the kind of dialogue that makes you feel like you’re sitting in on a real conversation—not a performance. If you’ve ever been interrupted mid-sentence, needed to vent, or just wanted to hear someone say “same,” this show is for you. To contact us, get your copy of Street Tales Volume One, shop the Street Tales Network Apparel (all proceeds go to Blue Cancer Connect), and gain access to all the podcast shows on our network, please go to: https://www.streettalesnetwork.com/

Publisher

iamtryingtohaveaconversationwithyou

Category

comedy

Language

en

Explicit

Yes

First episode

31 Jan 2026

Latest episode

24 Aug 2026

Latest episodes

18 episodes in the feed.

1. 

   24 Aug 2026

   Ep.18 .....With Sydney Symone (Audio)

   Kasha and Monique sit down with TikTok historian Sydney Simone for a fun, nostalgic trip through some of the most beloved sitcoms of the ’80s and ’90s. From A Different World and The Cosby Show to Living Single and beyond, they share hot takes, favorite characters, unforgettable theme songs, and the moments that made these shows so iconic. Sydney brings her unique perspective on the cultural impact of classic television, while the sisters debate which characters they loved, who they would want as family, and which TV personalities would make the perfect dinner guests. Expect plenty of laughs, candid opinions, childhood nostalgia, and a celebration of the sitcoms that not only entertained a generation but also helped shape culture, conversations, and the way we saw ourselves on television. NOTE: Due to an unexpected technical issue, Sydney Simone’s video was unavailable for approximately the final 15 minutes of the episode. Do not fret—the conversation continues, and you will not want to miss the fun! Sydney Symone TikTok - https://www.tiktok.com/@sydney.symone Instagram - https://instagram.com/trying2haveaconvopod TikTok - https://tiktok.com/@trying2haveaconvo Email - trying2haveaconvo@gmail.com Street Tales Network - https://streettalesnetwork.com/ To contact us, get your copy of Street Tales Volume One, shop our Street Tales Network apparel (all proceeds go to Blue Cancer Connect), and gain access to all the podcasts on our platform, please go to: https://www.streettalesnetwork.com/ #podcast #trying2haveaconvo #90ssitcoms #80stvshows #trending #youtube #Viral #FYP #tips #youtubeshorts #shorts #bluecancerconnect #blackoutcoffee

2. 

   16 Aug 2026

   Ep. 17 .....About AITA Reddit Stories (Audio)

   We’re BAAAAACK!  After a little hiatus, the sisters are back, bringing their signature chemistry, unfiltered opinions, and plenty of laughs.  Kasha and Monique return with an episode built around one of the internet’s favorite questions: Am I the A-hole? The sisters read and judge real-life “Am I the A**hole?” stories, tackling everything from a birthday dinner blowup and grandma’s babysitting boundaries to a friend who suddenly goes quiet, a sister who moves in uninvited, and the never-ending battle over after-hours work demands. As always, the verdicts come with plenty of blunt opinions, laughter, personal anecdotes, and a few moments of, “Oh, absolutely NOT!” Along the way, the sisters discuss family dynamics, parenting rules, friendship seasons, setting boundaries, and the importance of protecting your personal time. Join us for an entertaining conversation, because sometimes you need an honest sister’s perspective, sometimes you need a reality check, and sometimes… you just need to know if you’re the A**hole. So, whose side are you on?  And more importantly… ARE YOU AN A**HOLE?!

3. 

   21 Jun 2026

   Ep. 16 .....About Fathers

   In this special Father’s Day episode, sisters Kasha and Monique sit down with their father to explore his childhood, parenting journey, and the values that have guided both his life and theirs. Through heartfelt conversations and plenty of laughter, they revisit cherished family memories, childhood pranks, Fourth of July barbecues, and influential mentors. As they reflect on the lessons he has shared over the years, the conversation highlights themes of love, legacy, resilience, and the unique bond between parents and children. Their father offers practical wisdom, including his guiding philosophy to “be the best at whatever you do,” while Kasha and Monique share how his support, encouragement, and example helped them navigate life’s challenges. Filled with humor, nostalgia, and meaningful life lessons, this episode is a tribute to fathers everywhere and a celebration of the lasting impact parents have on their children. More than a conversation, it is a family keepsake designed to preserve stories, honor a legacy, and inspire future generations. To contact us, get your copy of Street Tales Volume One, shop our Street Tales Network apparel (all proceeds go to Blue Cancer Connect), and gain access to all the podcasts on our platform, please go to: https://www.streettalesnetwork.com/ LINKS Instagram - https://instagram.com/trying2haveaconvopod TikTok - https://tiktok.com/@trying2haveaconvo Email - trying2haveaconvo@gmail.com Street Tales Network - https://streettalesnetwork.com/ #podcast #trending #youtube #Viral #FYP #tips #youtubeshorts #shorts #bluecancerconnect #blackoutcoffee #fatherhood #familylegacy #generationalwisdom #familytraditions #childhoodmemories

4. 

   6 Jun 2026

   Ep. 15 .....About Birth & Postpartum (Audio)

   In this special episode, Monique and Kasha welcome their first-ever guest, Arielle, a former emergency room nurse and mom, for a candid and heartfelt conversation about pregnancy, birth, and the realities of postpartum life. Arielle shares her personal journey through motherhood, including her experience with postpartum depression and anxiety, the challenges of balancing a demanding healthcare career with raising a child, and the emotional toll that can come with major life transitions. Together, they discuss the importance of recognizing when help is needed, breaking the stigma surrounding maternal mental health, and finding a path toward healing. Through honest storytelling, practical advice, and plenty of relatable moments, the conversation explores how medication, therapy, lifestyle changes, and a strong support system can make a meaningful difference. This episode offers hope, encouragement, and reassurance for anyone navigating the ups and downs of motherhood or supporting someone who is. Join us for an authentic discussion filled with vulnerability, resilience, and the reminder that no one has to face postpartum struggles alone. To contact us, get your copy of Street Tales Volume One, shop our Street Tales Network apparel (all proceeds go to Blue Cancer Connect), and gain access to all the podcasts on our platform, please go to: https://www.streettalesnetwork.com/ #podcast #trending #youtube #Viral #FYP #tips #youtubeshorts #shorts #bluecancerconnect #blackoutcoffee #pregnancy #postpartumanxiety #postpartumdepression #mentalhealth #motherhood #realmotherhoodstories #birth

5. 

   23 May 2026

   Ep. 14 .....About Gen Xers vs Millennials (Audio)

   In this fun and hilarious episode, sisters Kasha and Monique face off in a lively Gen X vs. Millennial showdown! Through playful debates and plenty of laughter, they compare childhood games, cartoons, toys, music, technology, and partying while sharing nostalgic memories and hot takes from their generations. Structured like a friendly battle, each segment ends with a winner being declared as the sisters argue their case for why their generation did it better. From iconic childhood moments to the biggest cultural differences between generations, this episode is packed with humor, sharp arguments, and relatable throwback stories. Whether you are Team Gen X or Team Millennial, join us for a fun trip down memory lane and let us know which generation you think came out on top! Follow us on social media, share your childhood memories, and join the conversation on our platforms. LINKS Instagram - https://instagram.com/try2haveaconvopod TikTok - https://tiktok.com/@try2haveaconvo Email - try2haveaconvo@gmail.com Street Tales Network - https://streettalesnetwork.com/ To contact us, get your copy of Street Tales Volume One, shop our Street Tales Network apparel (all proceeds go to Blue Cancer Connect), and gain access to all the podcasts on our platform, please go to: https://www.streettalesnetwork.com/ #podcast #trending #youtube #Viral #FYP #tips #youtubeshorts #shorts #bluecancerconnect #blackoutcoffee #GenX #millennials #nostalgia #GenXwins #Millennialswin #Generationalbattle

6. 

   9 May 2026

   Ep. 13 .....About Mommas (Audio)

   In this Mother’s Day episode, sisters Monique and Kasha bring their mom, Patty, and their 95-year-old grandmother, Annie, together for a warm and honest conversation about motherhood across generations — and the unique experience of having four living generations in one family, including their children. The discussion weaves together personal stories and reflections, from tattoos and childhood fundraisers to the challenges of IVF and raising children at very different stages of life. Along the way, they explore the contrast between the dreams of becoming a parent and the realities that follow, offering grounded insight into what motherhood truly looks like in everyday life. They also share practical parenting wisdom, including the importance of structure, meeting basic needs, and building a strong “village” of support. At its heart, the episode reflects on the legacy of love, resilience, and imperfect parenting passed down through their family — and how those lessons continue to shape each generation. To contact us, get your copy of Street Tales Volume One, shop our Street Tales Network apparel (all proceeds go to Blue Cancer Connect), and gain access to all the podcasts on our platform, please go to: https://www.streettalesnetwork.com/ #podcast #trending #youtube #Viral #FYP #tips #youtubeshorts #shorts #bluecancerconnect #blackoutcoffee #MothersDay #4generations #motherhood #familybonds #generationalwisdom

7. 

   27 Apr 2026

   Ep. 12 .....About Unsolved Mysteries (Audio)

   In this episode, Monique and Kasha dive into the mysteries of ancient civilizations, unexplained phenomena, and the limits of human knowledge. With plenty of laughs along the way, they explore theories and share their own perspectives on some of the world’s most intriguing unsolved mysteries. From the Moai statues of Easter Island to the Bermuda Triangle and the enigmatic Voynich Manuscript, they examine compelling questions about our past and the unknown. The conversation also ventures into unexplained phenomena such as the Taos Hum, the Wow! Signal, crop circles, and the Nazca Lines—unpacking scientific theories, cultural significance, and the enduring mysteries that continue to challenge our understanding of the universe. To contact us, get your copy of Street Tales Volume One, shop our Street Tales Network apparel (all proceeds go to Blue Cancer Connect), and gain access to all the podcasts on our platform, please go to: https://www.streettalesnetwork.com/ #podcast #trending #youtube #Viral #FYP #unsolvedmysteries #extraterrestrial #youtubeshorts #shorts #bluecancerconnect #blackoutcoffee #livingblue

8. 

   18 Apr 2026

   Ep.11 .....About If I Were in Charge (Audio)

   In this episode, Queen Kasha and Queen Monique take the mic—crowns on and perspectives bold—as they dive into the thought-provoking theme, “If I Were in Charge…” Together, they share their insights on leadership, education reform, and the essential life skills needed for the future, offering practical strategies for decision-making, conflict resolution, and meaningful improvements within today’s school systems. The conversation unfolds into a lively and relatable discussion on societal norms—from school dress codes to workplace etiquette and even the unspoken rules of airplane behavior. With candid insights and plenty of humor, the queens challenge the status quo while imagining new laws and everyday changes that could make life run a little smoother. Tune in for a fun, honest, and empowering episode where Queen Kasha and Queen Monique bring wisdom, wit, and just the right amount of royal flair. To contact us, get your copy of Street Tales Volume One, shop our Street Tales Network apparel (all proceeds go to Blue Cancer Connect), and gain access to all the podcasts on our platform, please go to: https://www.streettalesnetwork.com/ #podcast #trending #youtube #Viral #FYP #tips #youtubeshorts #shorts #bluecancerconnect #blackoutcoffee #livingblue #IfIWereInCharge #LeadershipMatters #TeachTheFuture #ModernEtiquette #DressCodeDebate #WorkplaceCulture #AirplaneEtiquette #CrownedConversations #PodcastQueens #letstalkaboutit

9. 

   18 Apr 2026

   Ep.10 .....About Health (Audio)

   Today Monique and Kasha share funny, slice-of-life moments—from confetti-filled teacher pranks to gray-hair mishaps to a proud mom’s story about an 8-year-old’s unassisted triple play—before diving into a wide-ranging conversation about health. They redefine health beyond weight, exploring nutrition, strength, mobility, and mental and emotional well-being. The conversation emphasizes consistency over intensity, balanced eating over restrictive dieting, and questions common diet fads, the role of medical guidance in nutrition, and both personal and societal responsibility in making healthier choices. The episode also highlights global insights from the Blue Zones—Okinawa, Sardinia, Nicoya, Ikaria, and Loma Linda—focusing on the importance of strong social connections, regular movement, stress reduction, and mindful eating. Throughout, they emphasize the value of community, prayer or meditation, time in nature, and the idea that exercise is a celebration of what the body can do. To contact us, get your copy of Street Tales Volume One, shop our Street Tales Network apparel (all proceeds go to Blue Cancer Connect), and gain access to all the podcasts on our platform, please go to: https://www.streettalesnetwork.com/ #podcast #trending #youtube #Viral #FYP #tips #youtubeshorts #shorts #bluecancerconnect #blackoutcoffee #BlueZones #health #communityhealth #wellness

10. 

    30 Mar 2026

    Ep.9 .....With Fifty Sixi'N (Audio)

    In this episode, Monique and Kasha sit down with Tyler and BJ from their “brother podcast,” Fifty Sixi’N, for an honest and engaging conversation. They explore the dynamics of male and female friendships, emphasizing the importance of boundaries within co-ed relationships. The discussion expands to how marriage can shift these dynamics, and why trust and open communication are essential when maintaining friendships with the opposite sex. The conversation also dives into modern perspectives on romance, highlighting how it often centers around female pleasure and what that means for couples today. To wrap things up, the group keeps things relatable with a discussion on balancing different TV preferences with your partner—and how even that can become meaningful, intentional quality time. To contact us, get your copy of Street Tales Volume One, shop our Street Tales Network apparel (all proceeds go to Blue Cancer Connect), and gain access to all the podcasts on our platform, please go to: https://www.streettalesnetwork.com/ #podcast #trending #youtube #Viral #FYP #books #tips #youtubeshorts #shorts #bluecancerconnect #blackoutcoffee #RomanceisforFemales #coedfriendships #boundaries #WhatAreYouWatching

11. 

    21 Mar 2026

    Ep.8 .....About Social Media Too (Audio)

    In this episode, Monique and Kasha unpack how social media blurs reality, amplifies comparison, and alters relationships — from parenting and children's safety to adult mental health, algorithms, and parasocial connections. They explore platform responsibility, oversharing, dating in the digital age, and practical tips for setting boundaries so families and individuals can stay grounded online. To contact us, get your copy of Street Tales Volume One, shop the Street Tales Network Apparel (all proceeds go to Blue Cancer Connect), and gain access to all the podcast shows on our network, please go to: https://www.streettalesnetwork.com/ #SocialMediaImpact #MentalHealthMatters #MindfulOnline #ParasocialAwareness #ThoughfulTalks #podcast #trending #YouTube #Viral #Trending #FYP #BlueCancerConnect #YouTubeShorts #shorts #entrepreneurship #tips #BlackoutCoffee

12. 

    14 Mar 2026

    Ep.7 .....About Social Media (Audio)

    In this episode, Monique and Kasha trade stories about chaotic kindergarten classrooms while giving well-deserved praise to teachers. They then dive into the evolution of social media, tracing its path from Six Degrees to TikTok. Along the way, they explore both the benefits—like community building, networking, and support for people with rare illnesses—and the risks, including algorithms, misinformation, cyberbullying, and the impact on mental health, especially for children. Blending personal stories with practical advice on setting boundaries online, the episode wraps up with a call for listeners to share their own social media drama, surprises, and experiences.

13. 

    9 Mar 2026

    Ep.6 .....About Our Hot Takes (Audio)

    In this episode, Kasha and Monique serve up a mix of hot takes—mild, medium, and spicy—covering everything from the greatness of Oreo cookies and coffee to whether audiobooks should really count as reading. They dive into the quirks of morning people, debate the soullessness of minimalism, and share their strong preference for beverages served in glass. The conversation jumps across a wide range of topics, including the aesthetics of product packaging, the cultural significance of the Olympics, and the ever-present rivalry between iPhones and Androids. Along the way, they weigh in on tipping culture, argue about the merits of candy corn, and discuss whether baseball deserves more excitement. With plenty of humor and personal anecdotes, Kasha and Monique also tackle the classic dogs-versus-cats debate and reflect on parenting in public spaces, emphasizing the importance of teaching kids respect and boundaries. It’s a lively, relatable conversation full of laughs and unapologetic opinions.

14. 

    28 Feb 2026

    Ep.5 .....About Introspection (Audio)

    In this episode, Kasha and Monique unpack the power of introspection and how their generational perspectives shape the way they think, feel, and process the world around them. Together, they explore what introspection really means, how their minds work in real time, and how parenting, emotions, and lived experiences influence their inner dialogue. The discussion also touches on the brain as a "tool", the influence of past experiences, and the importance of self-analysis in decision-making. To close things out, they lighten the mood with their recurring segment, “What Are You Watching?”—sharing what’s currently on their screens and why they’re loving it… or not.

15. 

    21 Feb 2026

    Ep.4 .....About Love Again (Audio)

    Kasha and Monique, share stories about meeting their husbands, early dating moments, and the small gestures that turned into lifelong love. With humor and hard truths they discuss dating rules, marriage challenges, and the importance of connection.  The conversation also delves into heartbreak, healing, and the commitment required to maintain a loving relationship. They emphasize that love is not enough on its own and that respect, communication, and flexibility are crucial for a successful partnership. Ultimately, they conclude that fighting for love is essential, but there are boundaries that should not be crossed.

16. 

    14 Feb 2026

    Ep. 3 .....About The Many Faces of Love (Audio)

    In this engaging conversation, the sisters host a candid conversation about what love really means — how it starts as feeling and evolves into a daily choice. They explore familial, romantic, and friendship love, love languages, and how culture and media shape our expectations. They also discuss setting boundaries, prioritizing relationships, teaching love to children, and practical ways to show care beyond holidays and grand gestures.

17. 

    8 Feb 2026

    Ep.2 ..... About the Roots of Resolutions (Audio)

    Hosts Monique and Kasha explore the history and meaning behind New Year’s resolutions, why the “new year, new me” idea took hold, and how cultural and marketing forces shape our desire to change. They share personal stories about church fasts, the spiritual roots of fasting across religions, and how fasting can create focus, clarity, and dependence on God amid a culture of abundance. The discuss practical tips including daily micro‑habits, building systems and accountability, giving yourself grace for setbacks, and considering spring as a natural time to launch lasting change. #podcast #police #trending #youtube #Viral #Trending #FYP #Tips #books #livingblue #bluecancerconnect #booktok #youtubeshorts #shorts #entrepreneurship #tips #blackoutcoffee

18. 

    31 Jan 2026

    Ep.1 ..... About Us (Audio)

    Episode one introduces sisters Monique and Kasha, their close-but-different bond across a 12-year age gap, and why they started this podcast to share real, funny, and honest conversations. They preview show topics including motherhood, mental health, food and movie picks, guest interviews, and the occasional life rant — all in 45–60-minute weekly episodes that invite listener questions and feedback. To contact us, get your copy of Street Tales Volume One, shop the Street Tales Network Apparel (all proceeds go to Blue Cancer Connect), and gain access to all the podcast shows on our network, please go to: https://www.streettalesnetwork.com/ #podcast #police #trending #youtube #Viral #Trending #FYP #Tips #books #livingblue #bluecancerconnect #booktok #youtubeshorts #shorts #entrepreneurship #tips #blackoutcoffee

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Spotify

5.0 / 5

2 ratings

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Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.