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