Seeing Other People

Mika Ross, therapist and relationship coach, joins the podcast to talk about the parts of relationships nobody teaches you until you’re already in one. We talk about what it actually takes to build a healthy relationship beyond chemistry and compatibility, why communication is so much more complicated than “just talk about it,” and how to navigate conflict without letting resentment build. Mika al...

It’s Ilana’s birthday weekend, the Jets are (almost) back, and somehow the Jonas Brothers might be helping us reveal our baby’s gender?! We’re talking about how our very unserious idea turned into a viral campaign that actually got Joe and Kevin Jonas’ attention, plus birthday plans, the weird guilt of posting on social media when you haven’t texted people back, and a conversation about choosing t...

This week I'm answering seven listener questions, and somehow they all circle back to the same underlying thing: learning which feelings you can actually trust. I get into why not missing someone might mean secure instead of anxious, why every breakup doesn't mean you failed, and what it means when someone checks every box but still makes you feel unseen. I also cover the line between healthy comp...

Kelly Ehlers, award-winning founder, writer, speaker, podcast host, and author of Nice Girls Win , joins the podcast to unpack the invisible rules so many women live by — and what it looks like to choose yourself without blowing up your life. We talk about why being “nice” doesn’t have to mean being a people pleaser, how boundaries can actually make you a better nice girl, and why saying no doesn’...

Ilana's recording sick, the Syracuse course is officially over and she's not ready to talk about how much she'll miss it, and she saw Hilary Duff sell out MSG and has a lot of feelings. Two listener questions this week: how many drinks on a first date is too many (she ordered a third before he finished his first, and he was expected to pay), and he said after one great date that he doesn't want to...

Amanda Katz joins the podcast to share the story of ending a long-term relationship after realizing her partner never fully grasped that she truly did not want children. We talk about the difference between "maybe someday" and knowing something about yourself since you were eleven years old, why having a child to save a relationship never actually saves it, and the quiet, undramatic weeks when she...

Jordanne Sculler, licensed mental health counselor and relationship therapist, joins the podcast to unpack why so many of us keep repeating the same dating patterns—even when we know they're not working. We talk about the psychology behind unhealthy relationship cycles, why your "type" may actually be keeping you stuck, and how childhood experiences and old stories shape the way you approach love....

This week, a 4am pregnancy craving for a discontinued pasta dish spirals into one of the wildest nights of our lives, ending in a comped multi-course meal at Moriah, NYC's #1 Italian seafood restaurant, care of the original chef himself (Chrissy Teigen even weighed in). We check back in on Christmas Party guy, and the update isn't the one we were hoping for. A listener asks how engagement ring sho...

After the response to Part 1 , we had to do a Part 2. In this solo episode, I'm diving into even more questions that can help you make better dating decisions before you turn to your group chat. I talk about breaking unhealthy patterns, separating your worth from rejection, the difference between closure and wanting a different ending, knowing whether your standards are actually standards or just...

Courtney Kocak joins the podcast to share the unbelievable story behind her memoir Girl Gone Wild and the many rock bottoms that ultimately changed her life. We talk about surviving toxic relationships, chasing impossible dreams in Hollywood, the lessons she learned from heartbreak, why she kept repeating the same dating patterns, and the unexpected traffic ticket that completely changed her love...

Are we pregnant or am I pregnant? Jake says we. Ilana says she's the one with a baby in her belly. We also have to tell you about the TikTok that went viral, because Ilana posted a green screen video about her biggest pregnancy craving, a shrimp scampi from a restaurant that closed years ago, and the original chef DMed her and invited us to his Michelin star restaurant to make it off menu. Three l...

Corinne joins the podcast to share the story of calling off her engagement just four months before her wedding after eight years with the person she thought she'd marry. We talk about the pressure of leaving when your lives are completely intertwined, why wedding planning doesn't fix relationship problems, recognizing the difference between a hard relationship and the wrong relationship, and the t...

Dr. Darcy Sterling , licensed therapist, relationship expert, and host of We Need To Talk with Dr. Darcy Sterling , joins the podcast to unpack why so many people confuse anxiety with chemistry—and how our relationship patterns often keep us stuck dating the same types of people over and over again. We talk about why healthy love can initially feel unfamiliar, how childhood experiences shape attra...

Jake turns 33, we recap his birthday week, and Professor Ilana is two classes in and already never wants it to end. We get into everything we didn't have time for last week: the creative ways we told our friends we were pregnant, what the first trimester is actually like, and the part nobody warns you about: the waiting. Every appointment is a month apart and the anxiety in between is real. We als...

Olivia Atwood, Director of Matchmaking at Lox Club, joins the podcast to share how a joke matchmaking project during COVID turned into a career helping people find love—and what happened when she unexpectedly had to start dating again after the end of her own six-year relationship. We talk about dating in your 30s, the reality of dating apps, why so many people stay stuck chasing their "type," how...

Dr. Shamara Howard joins the podcast for an eye-opening conversation about how dating is changing—and why that's not necessarily a bad thing. We dive into why more women are choosing to stay single rather than settle, how to tell the difference between healthy standards and unrealistic expectations, and what it really means to protect your peace without closing yourself off to love. We also talk a...

We're pregnant, we're 15 weeks along, and we've been dying to tell you. This episode is everything: a clip from when we first found out, what the first trimester was actually like (the smell sensitivity, the endless weeks of feeling ill beyond belief, the food aversions, having to leave Carbone mid-dinner in Miami), how we told our families and so much more. We also want to acknowledge that this n...

After answering more than 10,000 dating questions over the years, I've realized something: most people don't actually need more advice. They need better questions. In this solo episode, I'm sharing the questions I wish everyone would ask themselves before asking their friends what to do. We talk about dating potential versus reality, the difference between evidence and assumptions, why you shouldn...

Linnea Sage joins the podcast to share how losing her voice acting career to AI unexpectedly led her to create The Jewish Dating Game, a live dating show helping singles connect beyond the apps. We talk about why modern dating feels so transactional, how first dates become interviews instead of experiences, why we often choose the wrong "type," and the simple ways to create genuine chemistry and c...

Barkley had us in a full panic leading us to the vet ER and then immediately ran laps around the facility like nothing happened. Ilana's Professor era officially begins this week, and we weigh in on the Taylor Swift and Travis Kelce MSG wedding because of course we do. Plus, listener questions: advice for someone trying to actually talk to people at dating mixers and speed dating events, and how t...

After reading 10,000+ dating and relationship questions, I've noticed that most people are asking the same thing in different ways: "How do I know I'm making the right choice?" In this solo episode, I'm breaking down four listener questions about anxiety, intuition, dating with intention, relationship doubts, and the pressure to know if someone is "the one." We talk about why modern dating feels s...

Therapist and co-host of the Therapy Brothers podcast, Tyler Patrick joins the podcast to share his personal story of addiction, betrayal, recovery, and rebuilding trust after everything fell apart. We talk about why betrayal feels so traumatic, what happens when shame keeps us stuck, how to heal when your nervous system is constantly on high alert, and the difference between surviving a betrayal...

Ilana's back on Love Island (long story), Jake played golf four times in eight days, and we're doing absolutely nothing for July 4th and couldn't be happier about it. Three listener questions this week: someone who got blindsided when a guy ended things just one week after they became exclusive — and how not to let it derail you from dating; the reality of being the single friend when all your clo...

In this raw and emotional follow-up to I Didn't Expect This Relationship to Break Me , an anonymous guest returns to share the final chapter of her story—and the moment she finally found the strength to walk away. After years of broken promises, emotional neglect, financial strain, and a relationship that left her feeling increasingly disconnected from herself, she opens up about what kept her stu...

Brandi Davis ( @backpocketcounseling ) joins the podcast for a deep dive into modern dating, relationship anxiety, communication, attachment styles, and the patterns that keep us stuck. As a licensed marriage and family therapist and founder of Back Pocket Counseling, Brandi shares why so many people feel exhausted by dating, how social media fuels comparison and self-doubt, the signs of emotional...