Seeing Other People

When this week’s guest decided to freeze her eggs at 30, she thought she was biding her and her husband time. Instead, she was hit with the news that she had a diminished ovarian reserve and that getting pregnant would be far more difficult than expected. In this episode, she opens up about the rollercoaster of fertility treatments, the pressure women carry when it comes to family planning, and ho...

Comedian Paul Schoenberg joins us today to get into why “nice guys” are often misunderstood, how texting culture has made rejection feel impersonal and confusing, and why so many people can’t recognize a red flag until they’re paying $2.99 a week just to text someone. We also talk about gluten, group chats, the emotional risk of being earnest, and why knowing what you want isn’t the hard part—find...

This week on Cohosts for Life , we’re diving deep into a tradition that’s become core to our relationship: the date list . We share how it started, why it’s surprisingly meaningful, and how it's helped us remember little memories that would've been lost to time. We also take a nostalgic walk through five years of Jake’s birthday celebrations — including what we did this past week. And, in true cha...

We’ve all got something we’re scared to talk about. Maybe you still live at home, haven’t had sex yet, just lost your job, or are quietly working through something painful. So many of us carry shame about parts of our lives we think others will judge, but the truth is, everyone’s going through something. In this solo episode, I’m talking about what it means to truly own your story. Not justify it....

Psychologist, relationship expert, and author Dr. Harry Cohen joins us to explain the power of being a “positive energizer,” what it really means to bring good energy into a room, and why it’s often the smallest things that make the biggest difference. We dive into how to show up better in your relationship, how to recover from mistakes without overprocessing, why most people give advice the wrong...

Ilana’s back from a fun bachelorette weekend in Maine and shares her travel nightmares, while Jake recaps his boys weekend with Barkley. Ilana’s riding high from her best long run yet, while Jake’s stuck on the couch dealing with his calf injury. We dive into the viral street-side walking debate that has TikTok roasting Jake for his so-called lack of etiquette. We break down what actually counts a...

When Waverly Colville signed a lease with a stranger named John Guilyard in the summer of 2020, she never imagined she was also meeting her future partner. Two years of friendship, late-night talks, and dancing around their feelings later, one kiss changed everything. In this episode, Waverly and John join us to share the real story of how they went from roommates to best friends to partners — and...

Breakups today aren’t just about letting go of a person — they’re about navigating texts, timelines, algorithmic reminders, and the pressure to "heal fast." Therapist and Lonely Hearts Club founder Lexi Joondeph-Breidbart joins Ilana to unpack what actually helps people move on, why we obsess over old messages, and how to know if it's time to unfollow, mute, or block your ex for good. @lonelyheart...

Welcome to the very first official episode of Cohosts for Life ! Ilana kick things off by explaining why this series exists, what inspired it, and what you can expect moving forward. Then we attempt to reintroduce each other before diving into a Q&A for you guys to know Jake more. We walk you through what to expect each week, from Ilana’s marathon training to Jake’s calf injury, what we’re lea...

In this Unfiltered, a listener shares the hard truths she’s learned through dating, heartbreak, and situationships. From realizing you can’t force someone to like you, to learning that overcompromising and over-efforting doesn’t lead to love, she reflects on the patterns she’s finally ready to break. If you’ve ever asked yourself why didn’t they choose me?—this one’s for you. ALL links here (datin...

Ryan Kenny, comedian and dater, joins me for a hilarious, honest convo on ghosting, dating app fatigue, and the awkwardness of putting yourself out there. We chat about exclusivity talks, bad sex with great people, and why women in friend groups are basically unapproachable. Follow Ryan @the_ryan_kenny and check out his upcoming show on July 8th in NYC! Learn more about your ad choices. Visit mega...

In this Unfiltered, a 39-year-old New Yorker opens up about dating a guy who was terrible for her, but ultimately changed her life for the better. Before, she was stuck in the “cool girl” role, hiding her needs and feeling constant anxiety. After this relationship led her to work with a relationship coach, she learned to be honest with herself and others and date without shame, leading to her now...

Dana, a 31-year-old nurse, shares how her seemingly “on track” life slowly unraveled in a toxic marriage that took a toll on her mental and physical health, even causing heart palpitations. After facing manipulation, family drama, and feeling like a stranger in her own life, Dana hit rock bottom — but that moment became the start of her healing. She opens up about rediscovering herself through the...

n this solo episode, I’m catching you up on life lately—books I'm reading, finishing my half marathon, how I feel about content creation right now, and whether I ever miss being single. I’m also answering your questions on dating app upgrades, chemistry that’s missing, ghosting after three great dates, confusing “what are we” situations, and wedding drama with a very pregnant bridesmaid. It’s hone...

Real world romance isn’t dead. It’s just been buried under algorithms and ghosting. That’s exactly why I partnered with Louis Jadot to host a Meet-Cute Master Class in NYC. In this episode, I’m sharing all of my best tips for creating your own meet-cute—how to start a conversation, feel more confident, spark something real without relying on the apps, and more. Pour a glass of Jadot and get inspir...

I’m joined by Han Huante , host of How I See It , for a vulnerable conversation about mental health, dating patterns, and the real (often messy) work of healing. We talk about how moving out of her comfort zone triggered depression and anxiety, how self-hatred shaped who she dated, and why being “real” with yourself is the first step toward real peace. Hannah opens up about choosing discomfort to...

I sit down with Danielle Dietzek and Julie Griggs, the cofounders of Fourplay Social ( @fourplaysocial ), for a real, unfiltered girl chat. We’re diving deep into what it feels like when your friends are hitting major life milestones like marriage, babies, and buying homes, while you're still single and wondering if you’re getting left behind. We talk about the pressure to define yourself by your...

We recorded this episode on our actual one-year anniversary, from Turks and Caicos! We set out to recap the year, and ended up talking about how Ilana ruined the surprise trip, little moments that brought us joy, and what our marriage actually feels like day to day. We answer listener questions about what the first year of marriage has really looked like, what we do and don't remember from our wed...

I’m joined by therapist Annie Josephson , PsyD, MSEd, Founder of Uptown Psychology to talk about why dating make us so anxious, even when it’s going well. We discuss why it shows up, how to manage it, and how to tell the difference between fear and intuition. We also answer listener questions about spiraling after dates, ghosting before anything starts, and feeling stuck in situationships. Subscri...

TW: This episode my be triggering to those with sensitivities around physical and emotional abuse. I’m joined by Ryan Spencer , who I met on the Tamron Hall Show, for a powerful conversation about healing, heartbreak, and holding out hope for love. Ryan opens up about leaving an abusive relationship, the strength it took to start over, and the frustration of wanting love so badly after doing the w...

This week, I’m joined by Syd Miller , founder of the fitness brand Housework . Syd shares how a breakup at 30, right when all her friends were getting engaged, became the catalyst for the best years of her life. We talk about how she built her brand from scratch, makes friends IRL, and navigates friendship shifts in different life stages. Most importantly, Syd shares how she’s created a full life...

TW: This episode includes discussion of sexual assault. This week, I’m joined by Meg Reynolds ( @meg_reynoldss ), host of Not the Girl Next Door ( @notthegirlnextdoorpodcast ), for a real conversation about healing after a hard relationship. We talk about relationship PTSD, rebuilding self-worth, why healing can take way longer than you expect, and how to stop shrinking yourself to be loved. If yo...

Jen Glantz ( @jenglantz ) has stood beside hundreds of brides—literally. As the founder of Bridesmaid for Hire and author of three books, she’s seen everything from dream weddings to full-on meltdowns. In this episode, she opens up about her own love story, what finally made her feel ready to say “I do,” and why she and her husband chose to elope after living out of suitcases and hopping cities. W...

Ilana is joined by Human Design expert and author Erin Claire Jones ( @erinclairejones ) to break down how understanding your unique design can shift the way you date, connect, and make decisions in love. Erin explains what Human Design is, how it compares to tools like astrology or the Enneagram, and how your chart reveals insights into your relationship patterns and emotional wiring. They talk a...

In this episode, Jake plays cohost as we’re joined by comedian and podcast host Jared Freid—someone who’s played an unexpectedly big role in our relationship. From being mentioned on our very first date to inspiring parts of our vows, Jared has been part of our love story from day one. We talk about the grind of building a show, what Jake has learned from Jared, and what it feels like to open a DM...