Seeing Other People

We announce a major life update, talk about how absurd the logistics of living in NYC are, and debate whether or not Ilana should start another new business. We also get into our favorite types of nights out (with each other, with friends, and with family), recap the funniest movie we’ve ever seen (no spoilers!), and complain about books that we hate and why it takes families forever to pick a mov...

On this Unfiltered, an anonymous guest opens up about how body image struggles, weight gain, and health issues in her mid-to-late 20s held her back from enjoying life — and almost stopped her from celebrating her own wedding. From dreading engagement photos and dress shopping to nearly eloping, she shares the turning point that changed everything and how she finally embraced the love and celebrati...

What really happens after someone cheats—and is there ever a way back? In this episode, I sit down with Dr. Monique Thompson, a licensed psychotherapist, bestselling author of the Infidelity Recovery Workbook for Couples . She reveals why “going back to the way it was” is never the goal, how to know if your discomfort is about your partner or your own unresolved past, and the science-backed number...

It's Ilana's 31st birthday! We're recapping a fun filled week including the Jonas Brothers concert that broke the internet, way too much sushi, and Jake's first attempt at painting pottery. We share an exciting and nerve wracking life update, and Ilana gets emotional thinking about what her 13 year old self would think of her 31 year old self. Submit your questions or share why you and your partne...

On this episode of Unfiltered, Sagari takes us through her powerful transformation from a self-proclaimed serial monogamist stuck in toxic relationship patterns to someone confidently single and truly thriving. She opens up about her breakup horror stories (yes, including one during a Broadway intermission), what kept her in relationships she knew weren’t right, and how she finally healed and reco...

This week, I’m joined by my run coach Victoria Sekely, DPT, for a candid conversation about living life on your own terms. We talk about the shocking way she met her husband, why she never wanted a traditional wedding, and her decision not to have kids. She shares how she navigates changing friendships as her friends become moms, finds fulfillment in other ways, and deals with people questioning h...

This week on Cohosts for Life, we’re talking about how our relationship wouldn’t exist without the Jonas Brothers (seriously), and how they’ve been woven into so many of our favorite memories. We share whether we would’ve been open to dating someone with a fandom as intense as our own (JoBros & Jets), and Ilana gives her honest thoughts on Jake’s Jets obsession. Plus, a recap of a jam-packed w...

Ilana sits down with Allie—an almost 30-year-old who’s never officially had a boyfriend despite years of dating in New York City. Allie opens up about the emotional complexity behind her dating experience, from living with anxiety to navigating body image struggles and self-doubt. They talk about the challenge of watching friends enter relationships while you’re still trying to “meet someone,” the...

TW: This episode may be triggering to those with sensitivities around sexual abuse. Fresh off a blindsided breakup, Amy Richman dives right back into dating while processing what happened. We debate the idea of soulmates, whether “right person, wrong time” is real, and what romance in relationships truly looks like. She also opens up about how a difficult first sexual experience affected her for y...

Ilana and Jake break down a whirlwind 10 days weeks that take them across four states, wrangling three dogs, surviving a six-hour quest for TikTok-famous pizza, and squeezing in a last minute night at the Comedy Cellar. Ilana tackles an unofficial half marathon, while the duo reflects on the agony of losing out on Gracie Abrams tickets, why it's okay that they often travel without each other, Jake...

We’re told that once we find the right person—boyfriend, fiancé, husband—everything will fall into place. But when I got the relationship I always wanted, I realized it didn’t magically fix my insecurities, anxiety, or self-worth. In this episode, I’m opening up about what didn’t get better in my relationship and the surprising things that actually helped me feel more confident, grounded, and whol...

Carli—friend and now 4x Unfiltered guest (you can catch her most recent episode linked below)—is back for a very real conversation about all the moments we ignore the red flags… until we can’t. We talk about brushing things under the rug, what it feels like to know something’s off but not be ready to walk away, and the pain of breaking up with someone you still love. We get into what it means when...

In this episode of Cohosts for Life, we’re taking you behind the scenes of our relationship—not just the milestones you see on social media, but the ones that shaped us the most. We walk through the major (and not-so-major) moments that brought us closer, the surprising moments that felt bigger than expected, and missed moments where we almost didn’t end up together. We also recap Jake’s birthday...

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...