In this episode of First Round’s On Me, we sit down with Lindsey Simcik — writer, mother, wife, and co-host of the global podcast phenomenon Almost 30 — for a powerful conversation about the “in-between seasons” of life: the moments where you don’t feel like yourself anymore, but you’re not quite sure who you’re becoming next.Lindsey opens up about building Almost 30 from a closet floor, why authenticity is the only thing that truly creates connection, and how so many people today are living in a constant state of performance — chasing validation, comparison, followers, and approval.We dive into anxiety as a messenger (not a monster), identity shifts through motherhood, resentment and guilt in early parenting, and the “unsexy” conversations that actually make relationships stronger, healthier, and yes… even sexier.This episode is honest, deeply grounding, and one of those conversations that makes you feel less alone — in your relationship, your parenting journey, your anxiety, and your becoming.💬 In the comments: What’s one “in-between season” you’re currently moving through?00:00 – Lindsey Simcik joins the show (Almost 30)02:50 – “What would you do if you had nothing to prove?”04:35 – Almost 30 started on a closet floor07:10 – Authenticity vs performance culture13:20 – Emotional communication in relationships19:10 – Motherhood myths, resentment & identity shifts26:10 – Fitness, self-care & parenting seasons30:10 – Forecasting your week (and planning intimacy)33:00 – Anxiety: label vs deeper meaning37:10 – Social media, kids & the next generation42:10 – Presence, phones & attention collapse45:20 – The season you’re in isn’t permanent48:00 – Closing thoughts & where to find Lindsey

In this episode of First Round’s On Me, we’re joined by Kalissa Persaud — actor, model, and creator — for a wide-ranging conversation about art, identity, confidence, and what it really means to build a creative career in the age of algorithms.

We talk about acting vs. content creation, why follower count is quietly reshaping opportunity, and how micro-influencers are becoming more trusted than celebrities. Kalissa opens up about rejection, craft, modeling for major fashion houses, and the pressure of growing up in industries that reward perfection while punishing humanity.

The conversation expands into AI in the arts, the danger of over-curation, confidence vs. self-belief, and why real connection — eye contact, presence, imperfection — is slowly disappearing in a hyper-digital world. At its core, this episode is a reminder that art is supposed to be human, not optimized.

Funny, thoughtful, and unexpectedly philosophical, this is a conversation about choosing belief in yourself when the world is constantly telling you who to be.

💬 In the comments: Do you think social media is helping or hurting creativity right now?

00:00 – Kalissa Persaud joins the show & modern acting

02:00 – Actors vs influencers: how opportunity is changing

05:00 – Self-love, confidence & identity

08:00 – Modeling, acting & finding your craft

11:00 – Rejection culture in creative industries

14:00 – Content creation vs trained performance

17:00 – Consistency over talent

20:00 – Belief in yourself & confidence erosion

23:00 – Social media as a double-edged sword

26:00 – Eye contact, presence & lost social skills

29:00 – Technology vs human connection

32:00 – AI in the arts: threat or tool?

35:00 – Why imperfection is essential to art

38:00 – Fashion as self-expression

41:00 – Discovering who you are beyond work

44:00 – Modeling, major brands & naïveté

47:00 – Final thoughts

In this episode of First Round’s On Me, Joey and Hannah pull back the curtain on why FROME evolved from a dating app into a social app — and what problem it’s actually trying to solve.They unpack the tension between technology and genuine human connection, the confusion users have felt around too many features, and why the simplest explanation is often the most powerful. From explaining the app in a single sentence to breaking down how drink credits, partner venues, and real-life meetups actually work, this episode is both a philosophy lesson and a practical reset.The conversation expands into Gen Z’s rejection of screen addiction, the growing “analog” movement, and why even the people who built social media won’t let their kids use it. At its core, this episode is about getting people off their phones and back in front of each other — using technology as a bridge, not a replacement, for real connection.If you’ve ever felt overwhelmed by group chats, endless scrolling, or plans that never actually happen, this episode explains why FROME exists — and why real connection still matters.💬 In the comments: Do you feel the shift toward more “analog” experiences happening already?00:00 – Technology vs genuine human connection 01:00 – Why FROME evolved from dating app to social app03:00 – The problem: too many features, unclear core message05:00 – Explaining FROME in one simple sentence06:30 – Turning group chats into real plans08:00 – Incentivizing real-life connection10:00 – Social media’s shift from “we” to “me”12:00 – The return to analog experiences14:00 – Gen Z, screen addiction & social media bans16:00 – Why tech founders don’t let their kids use screens18:00 – How FROME actually works (plans, credits, venues)21:00 – Why plans must involve other people23:00 – Capturing moments vs curating perfection25:00 – Why FROME isn’t Instagram or a dating app27:00 – Community feedback & simplifying the experience29:00 – Final thoughts: get off your phone, meet people29:40 – Outro & gratitude

In this episode of First Round’s On Me, we sit down with Jenny Gorelick — comedian, writer, and two-time Emmy-nominated producer — for a conversation that blends comedy, dating, fear, and emotional honesty in a way only a comic can.Jenny opens up about what’s actually changed for women in comedy (and what hasn’t), how she creates a sense of belonging in New York rooms, and why comedy is one of the hardest art forms in the world to get right. The conversation moves fluidly from stand-up and writing, to magic on stage, to pop culture, celebrity relationships, and the strange emotional logic of modern dating.We also dig deep into ghosting vs. honesty, fear of rejection, emotional intelligence, and why so many people avoid direct communication — even when they care. From “soft ghosting” debates to the truth behind “if he wanted to, he would,” this episode is sharp, funny, and uncomfortably relatable.💬 In the comments: Is soft ghosting ever okay — or is honesty always worth the discomfort?00:00 – Jenny Gorelick joins the show 02:00 – Creating belonging in New York comedy rooms04:00 – Emmy nominations, pride & creative identity06:30 – Comedy as a business vs. pure art08:30 – Why stand-up is one of the hardest jobs11:30 – What makes comedy actually work14:00 – Writing, timing & making effort feel effortless16:30 – Magic, performance & audience trust18:30 – Pop culture, celebrity breakups & public behavior21:00 – Dating confusion & miscommunication23:00 – Soft ghosting vs. emotional responsibility26:00 – Fear of rejection & avoiding honesty29:00 – “If he wanted to, he would” — not always true32:00 – Insecurity, courage & choosing discomfort35:00 – Dating advice for men in NYC38:00 – Final thoughts & outro

In this special holiday episode of First Round’s On Me, Joey and Hannah talk about the side of the holidays that rarely makes it into movies or Instagram posts — the heaviness, the distance, the awkward questions, and the quiet loneliness so many people feel this time of year.They open up about fractured family dynamics, spending Christmas alone, navigating intrusive questions about marriage and children, and the grief that comes not from loss — but from disconnection. This conversation is for anyone who doesn’t feel at home during the holidays, anyone returning to complicated family environments, and anyone trying to protect their peace while still craving connection.The episode explores how to set boundaries without blowing things up, why lowering expectations can save your mental health, and how chosen family can be just as meaningful as the family you’re born into. They also talk about creating new traditions, being vulnerable enough to ask for connection, and finding ways to make the holidays meaningful — even if they don’t look “perfect.”If the season feels heavy, this episode is here to remind you: you’re not broken, you’re not alone, and you’re allowed to do the holidays your own way.💬 In the comments: How do the holidays really feel for you this year?00:00 – Holiday pressure & intrusive family questions01:00 – Why the holidays are hard for so many people 03:00 – Different relationships with family & Christmas05:30 – Growing up with big family traditions07:00 – Spending Christmas alone & creating new traditions09:00 – Reframing loneliness during the holidays11:00 – Going home to difficult family dynamics13:00 – Boundaries vs. keeping the peace15:00 – Lowering expectations to protect your mental health17:00 – Chosen family & adult connection19:00 – Being vulnerable & asking for connection21:00 – Using FROME to meet friends, not just dates23:00 – Small gestures that create meaningful memories25:00 – Being present with parents & grandparents27:00 – Creating new traditions with your own family28:00 – Final reflections & holiday message

In this episode of First Round’s On Me, Hannah sits down with Lily Stewart — creator, style muse, “walking Pinterest board,” and one half of the internet’s most wholesome roommate duo.From NYC nightlife to the Soft Girl era, performative vulnerability, modern dating dynamics, and the chaos of Gen Alpha memes, this conversation is funny, warm, and surprisingly introspective. Lily opens up about friendship loyalty (including that dartboard incident), leaving the 9–5 world, building community, chasing creative freedom, and why confidence in dating is disappearing.The episode also dives deep into the “soft era of men,” performative therapy culture, emotional intelligence, parasocial relationships, and why—despite everything—real connection still matters more than ever.💬 In the comments: Are men really in their “soft era,” or is it just social-media performance?00:00 – Meet Lily Stewart & NYC creative life01:00 – Music taste, nostalgia & personality03:30 – Dating red flags & the dartboard story07:00 – Career pivots: leaving 9–5 for creativity10:00 – Entrepreneurship vs corporate life12:00 – Freedom, fulfillment & taking risks14:30 – Building community & true support17:00 – Social media: connection vs burnout20:00 – Parasocial dynamics & craving IRL community23:00 – Modern dating struggles & overthinking25:30 – Men’s “soft era” & performative vulnerability28:00 – Approaching people in public: why confidence is disappearing31:00 – Emotional intelligence, therapy culture & accountability34:00 – What women actually want: honesty, strength & maturity37:00 – Ending situationships respectfully40:00 – Lily’s next chapter & Freeform Studio42:00 – Outro

In this deeply honest episode of First Round’s On Me, Joey and Hannah unpack something almost every couple experiences — but very few talk about out loud: the six stages of marriage.From the fantasy phase to the frustration phase, from questioning everything to choosing each other again, this conversation is raw, vulnerable, and full of real-life moments that every long-term couple will recognize.They dive into postpartum identity shifts, sleep deprivation, resentment, rebuilding intimacy, rediscovering attraction, the danger of complacency, and what it means to truly choose your partner every single day.It’s an episode about love that evolves, grows, breaks, heals, and strengthens — not the fairytale version, but the real one.💬 In the comments: Which stage do you think most couples get stuck in?00:00 – “Will we ever be attracted to each other again?” 00:14 – The six stages of marriage01:16 – Sick babies, sleep regression & surviving together02:25 – “Is this normal?” — the moments every couple questions03:24 – Stage 1: The fantasy / honeymoon phase05:56 – Stage 2: The reality check07:48 – Moving in, masks off & unfiltered truth09:50 – Stage 3: Frustration — “Did I choose the right person?”12:45 – How long this stage lasts (and why many couples break here)14:18 – Missing your old life vs wanting the life you have16:26 – Repetition, resentment & learning not to spiral17:47 – Rediscovering yourself + rebuilding attraction18:49 – Stage 4: The growth phase19:31 – Choosing each other and choosing yourself20:36 – Postpartum bodies, confidence & honesty21:54 – “Are we still attracted to each other?”22:13 – Complacency kills everything23:13 – Stage 5: True love — bonded through storms24:35 – Seeing each other at your worst & still choosing to stay26:39 – Stage 6: The legacy phase — love that inspires27:46 – Marriage, family & the future you’re building29:24 – What people forget about growing old alone30:16 – What legacy do you want to leave?31:29 – Final thoughts & outro

In this episode of First Round’s On Me, Hannah sits down one-on-one with Tracy Sokat — dancer, content creator, founding trainer at Housework, and co-host of Fit Happens — for a deep, vulnerable conversation about fitness, confidence, body image, GLP-1 culture, and what it actually means to feel good in your skin.Tracy opens up about her journey from dance to teaching, the power of movement as community, and why fitness is just as much mental as it is physical. They explore GLP-1s and the new body conversation, transparency in a social-media-driven world, the psychology of comparison, and how to build confidence from the inside out.This episode is full of honesty, softness, humor, and wisdom — the kind of conversation that leaves you thinking long after it ends.💬 In the comments: What makes you feel the most confident?00:00 – Meet Tracy Sokat: dancer, creator & Housework trainer00:42 – The question everyone should answer truthfully03:12 – Tracy’s journey: dance, fitness & content creation05:20 – The mental side of movement07:29 – Community workouts vs. solo workouts08:12 – What is Housework?09:06 – How great instructors build loyalty10:00 – The Fit Happens podcast11:00 – Balance, lifestyle & realistic fitness12:12 – Intimidation in fitness & all-or-nothing culture14:26 – GLP-1s & the new body conversation18:40 – Body image, disordered eating & transparency20:00 – Being “seen” vs. being “healthy”22:04 – Should GLP-1 users be open about it?24:16 – Look good / feel good: what does it mean?26:14 – Comparison, confidence & grounding28:06 – Women, presentation & the male gaze30:14 – Self-discovery & peeling back layers33:59 – The mirror exercise: why you can’t lie to yourself35:10 – Connection rapid-fire: family, differences & purpose37:45 – “This is my sequel” — Tracy’s next chapter38:38 – Where to find Tracy + outro