Seeing Other People

Therapist Rebecca Marcus, LCSW, is back to talk about what it actually means to “do the work” in your love life. We unpack why awareness alone isn’t enough to break old patterns, how to tell the difference between real growth and just performing self-improvement, what to do if you’re doing everything “right” but still feel lonely, and whether it’s possible to over-communicate to the point it kills...

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 sometim...

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 w...

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...

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...

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 actuall...

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 t...

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...

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 (dati...

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 bet...

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 T...

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...

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 supp...

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 pa...

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...

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 do...

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...

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...

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...

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...

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 f...

I’m joined by dating coach and author Sabrina Bendory to unpack the game-changing concept of detachment — a mindset that transformed her love life and coaching approach. We dive into the fear of ending up alone and how to move through it, what real confidence feels like, how to stop obsessing over texts or social media, break overthinking cycles, and advice for being the only single friend in your...

Fresh off a 20 mile run I reflect on how I finally feel like I’ve turned a corner in marathon training. Jake earned some serious credit in the Husband Duties department so I share why expressing gratitude for each other matters. We talk about what we wanted to be when we grew up compared to how many kids now want to be influencers and wrap with a new game called “Popstar or Ilana” where Jake has t...

Cuffing season is here, but why does everyone suddenly want to couple up when the weather turns cold? In this episode, we dive into the psychology, cultural pressures, and real dating app data behind the phenomenon, plus practical tips to prepare—whether you’re looking for a winter fling or a long-term partner. Submit your questions or share why you and your partner are cohosts for life at ⁠ speak...

Divorce lawyer Jonathan Merel joins the podcast to share what he’s learned about love, marriage, and relationships from his years in family law. We talk about why couples file for divorce, how often people start the process but end up reconciling, what healthy couples have in common, and the truth about prenups. Jonathan also shares his personal perspective on love and commitment—and advice for co...