PODCAST · comedy
I AM TRYING 2 HAVE A CONVERSATION WITH YOU
by iamtryingtohaveaconversationwithyou
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.
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18
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 - [email protected] 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
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17
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?!
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16
Ep. 16 .....About Fathers (Audio)
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 - [email protected] Street Tales Network - https://streettalesnetwork.com/ #podcast #trending #youtube #Viral #FYP #tips #youtubeshorts #shorts #bluecancerconnect #blackoutcoffee #fatherhood #familylegacy #generationalwisdom #familytraditions #childhoodmemories
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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
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14
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 - [email protected] 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
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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
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ABOUT THIS SHOW
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.
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iamtryingtohaveaconversationwithyou
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