I’m fresh off a total bucket list moment, going back to Syracuse to speak at the launch of their new Center for the Creator Economy, and I’m bringing you along for the whole thing. I also share some big news with Jake live on the podcast, and his reaction does not disappoint. Jake talks about not leaving the apartment for 11 days after his surgery, and we reflect on the kind of support you sometimes need from your partner in those seasons. We get into the new Jonas Brothers Christmas movie, which Jake declared “the best Christmas movie ever” exactly 33 minutes in. And finally, I share a crazy full-circle update about the sign that got me through the hardest part of my marathon and how the people behind it ended up finding me. ALL links here (dating coaching, submit an anonymous Q, and more!)  Get $10 off your Nutrafol subscription at nutrafol.com promo code SEEINGOTHERPEOPLE Stock up on the best elevated essentials + get free shipping & 365 day returns at Quince.com/seeingotherpeople  Get 25% Off @CowboyColostrum with code SEEINGOTHERPEOPLE at www.cowboycolostrum.com. #CowboyColostrumPod  Your mental health matters. Head to rula.com/seeingotherpeople to connect with a licensed therapist who truly cares Start your guilt-free journey with the Good Habit. Use code SEEINGOTHERPEOPLE to get a free gift with purchase at tryfum.com/SEEINGOTHERPEOPLE. If you’re thinking about pregnancy or already on that journey, don’t settle for less than evidence-based support. My listeners get early access to Ritual’s Black Friday sale — 40% off your first month at Ritual.com/SEEINGOTHERPEOPLE See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this solo Q&A, I’m answering your dating and life questions — from moving cities for love to figuring out if you’re settling in your career. We get into what to do when your best friend disappears into a new relationship, how to tell if someone actually likes you, and the truth about not having it all figured out at 29. I also share my thoughts on wedding planning stress, dating apps, and why being single isn’t something to “fix.” It’s a mix of honesty, comfort, and real talk about what growing up in your 20s and 30s actually feels like. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Kelly Chase (@chaselifewithkelly) opens up about what really happened after Love Is Blind, the trauma, the healing, and how she learned to love herself again. From people-pleasing to personal growth, she shares how therapy, mindset coaching, and deep self-work helped her rediscover her worth. We talked about rebuilding after being misunderstood, reclaiming your story, and learning to date yourself before anyone else. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Jake’s been recovering from surgery with nonstop movie marathons, while I got upsold by a facialist and found myself spiraling about Botox because everyone around me seems to be doing it. I’m also on the hunt for a new hobby now that my running era has ended (open to suggestions). This week, I’m heading up to Syracuse to speak on a college alum panel (!!). Plus, we’re diving into the viral British Vogue article asking the question: is having a boyfriend embarrassing? ALL links here (dating coaching, submit an anonymous Q, and more!)  Get $10 off your Nutrafol subscription at nutrafol.com promo code SEEINGOTHERPEOPLE Stock up on the best elevated essentials + get free shipping & 365 day returns at Quince.com/seeingotherpeople  Get 25% Off @CowboyColostrum with code SEEINGOTHERPEOPLE at www.cowboycolostrum.com. #CowboyColostrumPod  Your mental health matters. Head to rula.com/seeingotherpeople to connect with a licensed therapist who truly cares Start your guilt-free journey with the Good Habit. Use code SEEINGOTHERPEOPLE to get a free gift with purchase at tryfum.com/SEEINGOTHERPEOPLE. If you’re thinking about pregnancy or already on that journey, don’t settle for less than evidence-based support. My listeners get early access to Ritual’s Black Friday sale — 40% off your first month at Ritual.com/SEEINGOTHERPEOPLE See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Heidi Friedman (@lovelessons104) went on 104 dates before finding the love of her life — and every single one taught her something new. A divorced mom of two (and now a bonus mom of two more), she opens up about realizing she was never truly in love with her ex-husband, rebuilding her confidence, and finally finding the kind of love she used to only hear about. We talk about what real love actually looks like, how to tell the difference between red flags and fear, and why being single might be the most powerful time of your life. Whether you’re on your first date or your 104th, this one will change how you think about love. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

I trained for months dreaming of the NYC Marathon finish line… and instead found myself sitting on the side of the course having a panic attack at mile 6. In this episode, Jake and I break down everything — from the logistics and the high of those first few miles, to the moment everything changed, why I kept going, and what I learned from one of the hardest days of my life. Jake also shares what the day was like from his side — the expectations vs. reality of being a spectator, and what it’s really like to support someone through the marathon experience. ALL links here (dating coaching, profile revamp, marathon fundraiser, and more!)  Get $10 off your Nutrafol subscription at nutrafol.com promo code SEEINGOTHERPEOPLE Stock up on the best elevated essentials + get free shipping & 365 day returns at Quince.com/seeingotherpeople  Get 25% Off @CowboyColostrum with code SEEINGOTHERPEOPLE at www.cowboycolostrum.com. #CowboyColostrumPod  Your mental health matters. Head to rula.com/seeingotherpeople to connect with a licensed therapist who truly cares Start your guilt-free journey with the Good Habit. Use code SEEINGOTHERPEOPLE to get a free gift with purchase at tryfum.com/SEEINGOTHERPEOPLE. If you’re thinking about pregnancy or already on that journey, don’t settle for less than evidence-based support. My listeners get early access to Ritual’s Black Friday sale — 40% off your first month at Ritual.com/SEEINGOTHERPEOPLE See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Most of us never learned how to talk about sex—so we assume everyone else just figured it out. Sex therapist Vanessa Marin and her husband Xander Marin join me to talk about what really makes intimacy last, why communication in the bedroom matters more than chemistry, and how to start conversations about sex before it becomes a problem. We dive into the myths that make us feel broken, how to keep desire alive when life gets busy, and the simple daily rituals that help you reconnect with your partner in 36 seconds flat. If you’ve ever felt awkward bringing up what you want—or wondered why your sex life doesn’t “just work”—this one will change the way you think about connection, desire, and real intimacy. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Dating advice is everywhere, but most of it is useless. From ghosting after a “perfect” date to why playing hard to get always backfires, Logan Mahan—writer of Take It From a Woman at InsideHook—shares what women actually want, the mistakes men don’t realize they’re making, and the small shifts that can completely change your dating life. Follow Logan on Instagram @loganspants ALL links here (dating coaching, profile revamp, marathon fundraiser, and more!)  Get $10 off your Nutrafol subscription at nutrafol.com promo code SEEINGOTHERPEOPLE Stock up on the best elevated essentials + get free shipping & 365 day returns at Quince.com/seeingotherpeople  Get 25% Off @CowboyColostrum with code SEEINGOTHERPEOPLE at www.cowboycolostrum.com. #CowboyColostrumPod  Your mental health matters. Head to rula.com/seeingotherpeople to connect with a licensed therapist who truly cares See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

So many of us were taught how to be chosen instead of how to choose. In this episode, writer, filmmaker, and podcast host Rory Uphold (Crimes of the Heart) joins me to talk about unlearning the dating rules that keep us stuck, why self-trust is the most underrated green flag, and how to finally stop settling for people who breadcrumb you. We dive into the fear of being single, the difference between intuition and anxiety, and the quiet confidence that changes everything about how you date. Rory shares how to rewire the beliefs that keep you chasing validation, what “fun certainty” really means, and why the right person will never make you question your worth. ALL links here (dating coaching, profile revamp, marathon fundraiser, and more!)  Get $10 off your Nutrafol subscription at nutrafol.com promo code SEEINGOTHERPEOPLE Stock up on the best elevated essentials + get free shipping & 365 day returns at Quince.com/seeingotherpeople  Get 25% Off @CowboyColostrum with code SEEINGOTHERPEOPLE at www.cowboycolostrum.com. #CowboyColostrumPod  Your mental health matters. Head to rula.com/seeingotherpeople to connect with a licensed therapist who truly cares See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Ilana is one week out from the marathon and feeling overwhelmed with everything happening at once. Jake asks how she’s holding up and shares how he’s feeling ahead of his surgery. We get into Jake’s dating history, the hilarious story of his first kiss, how his work schedule kept him from dating for years, and why we’re glad we didn’t meet any earlier. We also talk about Season 2 of Nobody Wants This and the parallels between the couples on the show and our own relationship. Listener questions include handling a partner who hasn’t said “I love you” yet and believing good guys are still out there. ALL links here (dating coaching, profile revamp, marathon fundraiser, and more!)  Get $10 off your Nutrafol subscription at nutrafol.com promo code SEEINGOTHERPEOPLE Stock up on the best elevated essentials + get free shipping & 365 day returns at Quince.com/seeingotherpeople  Get 25% Off @CowboyColostrum with code SEEINGOTHERPEOPLE at www.cowboycolostrum.com. #CowboyColostrumPod  Your mental health matters. Head to rula.com/seeingotherpeople to connect with a licensed therapist who truly cares See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

I’m breaking down the exact things that helped me get over crushes I was never even technically with. From muting people like it’s a form of therapy to distracting myself with run clubs, puzzles, and absurdly dramatic TV shows, I’ve mastered the art of an emotional reset. If you’re spiraling over someone who was barely in your life, consider this your permission to move on for real. ALL links here (dating coaching, profile revamp, marathon fundraiser, and more!)  Get $10 off your Nutrafol subscription at nutrafol.com promo code SEEINGOTHERPEOPLE Stock up on the best elevated essentials + get free shipping & 365 day returns at Quince.com/seeingotherpeople  Get 25% Off @CowboyColostrum with code SEEINGOTHERPEOPLE at www.cowboycolostrum.com. #CowboyColostrumPod  Your mental health matters. Head to rula.com/seeingotherpeople to connect with a licensed therapist who truly cares See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Dr. Molly Burrets called off her own wedding—and it changed everything. She shares the story of what led her to make that difficult decision, the self-reflection and work she realized she needed to do afterward, and how she eventually married the love of her life. We dive into the fear of shame and embarrassment that often comes with calling off a wedding—and why the reality is often far more supportive than you might expect. Molly also breaks down how to tell if your doubts are coming from anxiety or intuition, and walks through the key questions you should ask yourself if you’re unsure about ending a relationship.Whether you’re engaged, in a long-term relationship, or just curious about navigating bigALL links here (dating coaching, profile revamp, marathon fundraiser, and more!)  Get $10 off your Nutrafol subscription at nutrafol.com promo code SEEINGOTHERPEOPLE Stock up on the best elevated essentials + get free shipping & 365 day returns at Quince.com/seeingotherpeople  Get 25% Off @CowboyColostrum with code SEEINGOTHERPEOPLE at www.cowboycolostrum.com. #CowboyColostrumPod  Your mental health matters. Head to rula.com/seeingotherpeople to connect with a licensed therapist who truly cares emotional decisions, this episode is full of practical guidance and compassionate insight. Follow Dr. Molly at @drmollyburrets and learn more at www.drmollyburrets.com See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Jake and I are back reflecting on how good it feels to be surrounded by reliable people, the upgrades we’ve made to our apartment, and all the business ideas we’ve had but never acted on. Then we get into the big questions: did dating apps actually make dating easier or just more exhausting? Are you even allowed to date someone who’s allergic to your favorite food? We compare the best and worst parts of being single versus being partnered, and wrap with a wild “Am I The Asshole?” listener scenario involving a self-destructive friend who hooked up with another friend’s boyfriend. ALL links here (Submit a Q, schedule a call with me, marathon fundraiser, and more!)  Get $10 off your Nutrafol subscription at nutrafol.com promo code SEEINGOTHERPEOPLE Stock up on the best elevated essentials + get free shipping & 365 day returns at Quince.com/seeingotherpeople  Get 25% Off @CowboyColostrum with code SEEINGOTHERPEOPLE at www.cowboycolostrum.com. #CowboyColostrumPod  Your mental health matters. Head to rula.com/seeingotherpeople to connect with a licensed therapist who truly cares See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

I’m joined by Judit, a 49-year-old woman living in Barcelona who has never been married and is opening up about what it’s really like to be single at this stage of life. She shares what she wishes she could tell her 30-year-old self about dating, how the landscape has shifted from pre-apps to today, and how she responds when people ask, “why are you still single?” Whether you’re panicking in your late 20s or feeling the pressure in your 30s, this conversation is a powerful reminder that timelines are made up and there’s more than one path to happiness. Follow Judith on IG @it.is.miranda.time and grab a copy of her book https://natodating.com/ ALL links here (dating coaching, profile revamp, marathon fundraiser, and more!)  Get $10 off your Nutrafol subscription at nutrafol.com promo code SEEINGOTHERPEOPLE Stock up on the best elevated essentials + get free shipping & 365 day returns at Quince.com/seeingotherpeople  Get 25% Off @CowboyColostrum with code SEEINGOTHERPEOPLE at www.cowboycolostrum.com. #CowboyColostrumPod  Your mental health matters. Head to rula.com/seeingotherpeople to connect with a licensed therapist who truly cares See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

If you’ve ever stressed about your biological clock or worried what your future fertility might look like, this episode is for you. I’m joined by Kirsten Karchmer, a reproductive health expert who’s worked with over 10,000 couples through infertility and founded Conceivable to make care more effective and accessible.We talk about the signs in your cycle you shouldn’t ignore, what you can start doing now—before you even have a partner—to support your fertility, and how stress, relationships, and self-advocacy all play a role. Kirsten’s advice will leave you feeling informed, empowered, and more in control of your future. https://conceivable.com/ https://www.tiktok.com/@yourfertilityexpert https://www.tiktok.com/@theperiodexpert See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Ciao! We’re back from Italy and breaking down the highlights! Jake crushed it on the golf course while I ate spaghetti pomodoro every single day with no regrets. We talk about bringing your partner on a family trip, being creatures of habit, and then dive into your answers to my Instagram polls. If a relationship feels good but something is missing, is that enough to leave? Would you date someone who checks every box but doesn’t excite you? Are you settling without realizing it? We read your submissions and debate which hit home the most. ALL links here (submit a Q, dating coaching, profile revamp, and more!)  Get $10 off your Nutrafol subscription at nutrafol.com promo code SEEINGOTHERPEOPLE Stock up on the best elevated essentials + get free shipping & 365 day returns at Quince.com/seeingotherpeople  Get 25% Off @CowboyColostrum with code SEEINGOTHERPEOPLE at www.cowboycolostrum.com. #CowboyColostrumPod  Your mental health matters. Head to rula.com/seeingotherpeople to connect with a licensed therapist who truly cares See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this solo episode, I get vulnerable about a big life change I’m going through and what it’s teaching me about growth, and timing. I break down two listener scenarios: one from someone in a long-term relationship wondering if they’re settling because the spark feels missing, and another from a single listener questioning whether to lower their standards or stay single while searching for someone who truly excites them. We unpack the difference between healthy standards and unrealistic checklists, attraction versus compatibility, and how to trust yourself when it comes to matters of the heart. ALL links here (dating coaching, profile revamp, marathon fundraiser, and more!)  Get $10 off your Nutrafol subscription at nutrafol.com promo code SEEINGOTHERPEOPLE Stock up on the best elevated essentials + get free shipping & 365 day returns at Quince.com/seeingotherpeople  Get 25% Off @CowboyColostrum with code SEEINGOTHERPEOPLE at www.cowboycolostrum.com. #CowboyColostrumPod  Your mental health matters. Head to rula.com/seeingotherpeople to connect with a licensed therapist who truly cares See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Conversations with the people we love can feel harder than ever, but small shifts in how we listen and speak can completely transform your connections. I talk with New York Times bestselling author Charles Duhigg (Supercommunicators, The Power of Habit) about how to navigate tricky conversations, build trust, and create deeper connection in dating, relationships, friendships, and family. ALL links here (dating coaching, profile revamp, marathon fundraiser, and more!)  Get $10 off your Nutrafol subscription at nutrafol.com promo code SEEINGOTHERPEOPLE Stock up on the best elevated essentials + get free shipping & 365 day returns at Quince.com/seeingotherpeople  Get 25% Off @CowboyColostrum with code SEEINGOTHERPEOPLE at www.cowboycolostrum.com. #CowboyColostrumPod  Your mental health matters. Head to rula.com/seeingotherpeople to connect with a licensed therapist who truly cares See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Live from Italy, Jake and I are recapping the Jewish holidays, what stuck with us from the rabbi’s sermon, and what it was like hosting a holiday for the first time. We’re sharing the highs and lows from our travel day to Puglia, including our very first business class flight and whether we think it’s worth the hype. Then we answer listener questions: what to do when your sister gets engaged while hiding emotional cheating, whether random selfies from someone you're dating signal interest, and if it’s a bad sign when someone goes on vacation and never texts first. ALL links here (Listener Questions, dating coaching, profile revamp, marathon fundraiser, and more!)  Get $10 off your Nutrafol subscription at nutrafol.com promo code SEEINGOTHERPEOPLE Stock up on the best elevated essentials + get free shipping & 365 day returns at Quince.com/seeingotherpeople  Get 25% Off @CowboyColostrum with code SEEINGOTHERPEOPLE at www.cowboycolostrum.com. #CowboyColostrumPod  Your mental health matters. Head to rula.com/seeingotherpeople to connect with a licensed therapist who truly cares See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

My best friend and former Life in Progress cohost, Carly Silverman, joins me for a catch-up on pregnancy, friendship, and how our relationship has evolved as we’ve moved into different chapters of life. We talk jealousy, long-distance best friendship, what we miss from our Life in Progress era, and what excites us most about what’s ahead. ALL links here (dating coaching, profile revamp, marathon fundraiser, and more!) Get $10 off your Nutrafol subscription at nutrafol.com promo code SEEINGOTHERPEOPLE Stock up on the best elevated essentials + get free shipping & 365 day returns at Quince.com/seeingotherpeople  Get 25% Off @CowboyColostrum with code SEEINGOTHERPEOPLE at www.cowboycolostrum.com. #CowboyColostrumPod  Your mental health matters. Head to rula.com/seeingotherpeople to connect with a licensed therapist who truly cares See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.