Seeing Other People

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 hav...

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 d...

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. W...

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, pro...

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...

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!)

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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 group.

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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 to guess if dramatic song ...

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 speakpipe.com/sop

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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 couples looking to strengthe...

Jake and I are officially in our new apartment (!!) and we’re unpacking all the highs and lows of moving week — including Ilana’s unexpected side gig babysitting our TaskRabbit’s kid. We also get into what it’s like being in the thick of marathon training, the gorgeous wedding we just went to, and our hot take on why wedding speeches matter way more than people think.

Book a move with Roadway here and use code ilanadunn10 ...

I’m joined by musician Brett Altman, who recently left his finance career of 9 years to finally pursue music full-time and discovered that owning your story can completely change the way you date. We get into why you should never shrink yourself for someone who sees parts of you as a red flag, how to actually meet people IRL (yes, even at a bar), and what it takes to make a friends-with-benefits situation successful. Brett...

Miriam Katz just launched one of the boldest projects in the dating world: a podcast where she interviews every single person she’s ever dated. They talk about what it’s really like to sit down with exes face-to-face, and the surprising insights Miriam has gained about love, closure, and self-discovery along the way. Ilana and Miriam also explore how past relationships shape us, the challenges of turning personal history i...

It’s our final episode in this apartment before the big move, and Ilana’s type A side is showing in full force during the packing process. In between boxes, we answer your questions about dating and relationships. We talk about whether it’s a red flag if someone doesn’t text while they’re away, what to do when you can’t stop thinking about the guy who wasn’t ready, how to move forward when something casual is rekindled, an...

In this solo Q&A, I’m answering your biggest dating and friendship dilemmas — from why your ex still watches your Instagram stories, to how to say no to being a bridesmaid, to figuring out if “I’m not ready for a relationship” is the truth or just an excuse. We’ll talk jealousy, first dates, situationships, and how to trust again after heartbreak.

Submit your questions or share why you and your partner are cohosts for ...

After years of back-to-back heartbreaks, author Abby Rosmarin hit relationship rock bottom and made a radical decision: she stopped dating—completely—and committed to an entire year of choosing herself. Abby shares how she went from chasing love to enjoying her own company, and rebuilding from the inside out. We talk about loneliness, self-discovery, codependency, sexuality, and why, for her, being single with cats really...

This week we’re recording from Jake’s childhood bedroom, which of course led us to wonder what 13-year-old Jake would think of his life now. We share our life updates, what we’re grateful for, how we started packing way too early, and how football season is going to affect when we see each other. Then we dive into fall date activities—everything from apple picking to haunted houses—and decide which ones we’d actually do an...

Trigger Warning: Abuse. This anonymous guest shares the story of being with her ex for over eight years, navigating betrayal, abuse, and heartbreak—including infidelity, a pregnancy, and the chaos of planning a wedding that never happened. She reveals how their relationship ended abroad just weeks before her wedding, the shocking ways her ex continued his betrayal, and the lessons she learned about boundaries, self-worth, ...

I'm joined by my friend, fashion designer and founder of Maison Des Nus, Balim Tezel. We talk about what it’s like to build a life from scratch—moving to the U.S. for college, creating a chosen family in NYC, and launching the brand she dreamed of since childhood. Balim shares what dating for the first time in her twenties taught her about herself and what she was looking for, how she unexpectedly met her boyfriend Vinnie,...