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