This week on The Sheridan Show, Sheridan sits down with Trill AC, founder of Krew Season and Trill Academy and a familiar voice from Tonight's Conversation, for an unfiltered conversation about modern dating, relationships, and the expectations we place on ourselves and each other.

From dating fatigue and unrealistic standards to gender roles, submission, and the sacrifices men and women make in relationships, nothing is off the table. They unpack how social media shapes our idea of the perfect partner, why communication can feel so complicated, and whether we're asking for things in relationships that we're not willing to give ourselves.

Plus, Sheridan and Trill talk about entrepreneurship, building a platform, navigating criticism, and knowing when to tune out the noise.

Your homework this week: Take a look in the mirror. Before focusing on what someone else needs to bring to the table, ask yourself what you're bringing and whether you're becoming the person you want to attract.

Special shoutout to Rotimi and HIStory Grooming Co. for opening their doors so we could film this episode! We appreciate you!

The Sheridan Show is a space for candid conversations, curiosity, and the occasional side quest. Catch new episodes every Thursday, or join the conversation live on YouTube Mondays at 8 PM CT / 9 PM ET.

Stay curious. Be Untamed.

In this episode of The Sheridan Show, Sheridan sits down with Rotimi of HISTory Grooming Co for an open conversation about entrepreneurship, marriage, fatherhood, men's mental health, and the pressure to succeed without losing yourself in the process.

Rotimi shares how touring with Maxwell changed his perspective on success and being present for his family, why men need safe spaces to be vulnerable, and how he's creating room for those conversations through his work as a barber.

Plus, we're getting into What's Tea? 👀 From Kendrick Sampson's perspective on having children with platonic friends to the debate surrounding Savannah James and April McDaniel's first-class travel arrangements, we're exploring the expectations we place on relationships, friendships, and each other.

In this episode, we explore:

• The balancing act of ambition, marriage, and fatherhood
• Why men's mental health and community matter
• Redefining success as your priorities change
• The emotional labor of parenting and relationships
• Money, friendship, and unspoken expectations

Whether you're building a business, raising a family, or simply figuring out what success means to you, this conversation might challenge how you think about having it all.

Join the conversation! What does having it all mean to you?

🎥 Catch The Sheridan Show LIVE every Monday at 8 PM CT / 9 PM ET on YouTube. Full episode replays drop Thursdays.

Subscribe, rate, and share the show with someone who needs to hear this conversation.

Just do the thing. Live audaciously. Be untamed.

The Sheridan Show is where curiosity meets conversation.

Hosted by Sheridan Labbé, the show brings together entrepreneurs, creatives, entertainers, thought leaders, and everyday people with perspectives worth hearing for honest conversations about life, culture, relationships, money, creativity, ambition, and everything in between.

Expect thoughtful conversations, unexpected perspectives, plenty of laughs, and a few side quests along the way.

Because the best conversations aren’t about having all the answers. They’re about being curious enough to ask better questions.

Subscribe now and join the conversation.

Curiosity changes everything. The Sheridan Show is where it begins.

This week, Sheridan is joined by her friend Ana in New York City for a conversation about honoring your creativity, taking chances, and making room for all the different parts of who you are.

Ana is a software engineer with a lifelong love of music and singing, and the two get into what it looks like to balance an analytical career in tech with the freedom it takes to create. They talk about Ana’s move to New York, taking opportunities even when they’re scary, letting go of perfectionism, and why everything you love doesn’t have to become something you monetize.

Plus, Sheridan and Ana get into the A Different World reboot and its messy relationship dynamics, Drake’s FOMO, climate change, Side Quests, Sydney Sweeney, sports betting, and the unexpected tangents that come with a live conversation.

This week’s homework: If there’s something you really want to do, don’t let fear stop you. Take the chance, even if you don’t know exactly how it’s going to turn out.

The Sheridan Show is all about staying curious, having honest conversations, and figuring things out in real time.

New podcast episodes every Thursday.

Watch The Sheridan Show LIVE every Monday at 8 PM CT / 9 PM ET on YouTube.

Stay curious. Be untamed.

This week, Sheridan is joined by her friend Symone in Washington, D.C. for a conversation that goes just about everywhere.

They talk age gaps and the double standards around older men versus older women dating younger, beauty enhancements and cosmetic procedures, spontaneous side quests, surrogacy, job interview etiquette, and the beauty standards women navigate along the way.

Plus, Sheridan and Symone leave everyone with one assignment for the week: go on a side quest.

The Sheridan Show is about raw, curious conversations without judgment, because sometimes the most interesting conversations happen when you’re willing to ask the question and see where it goes.

New episodes every Thursday. Catch the show LIVE Mondays at 8 PM CT / 9 PM ET on YouTube.

We get into AI and whether we're using it too much, career decisions other people didn't understand, the side quests making life more interesting, friendship, relationships, and whether you can genuinely be happy for a friend when they get something you desperately want for yourself.

We also pull questions from a hat and talk about things we've done for love, financial decisions we'd never make again, toxicity in relationships and friendships, and whether we've ever had to admit that maybe we were the toxic one.

Plus, a little pop culture, a few unexpected tangents, and plenty of opinions along the way.

Your homework this week: Find a side quest. Do something different. Explore.

Watch The Sheridan Show live every Monday at 8 PM CT / 9 PM ET on YouTube, with new podcast episodes every Thursday.

Just do the thing. Live audaciously. Be Untamed.