Seeing Other People

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, an...

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 betw...

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 ...

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 expe...

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...

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 pr...

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.

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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...