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 megaphone.fm/adchoices
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 connecting with people who don’t trigger her fears. ALL links here (dating coaching, profile revamp,...
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 therapy, self-care, and leaning on her family, and how she’s now focused on rebuilding her independence...
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 honest, a little messy, and very real. Subscribe to our Patreon show Cohosts for Life for weekly bonus e...
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 inspired to make your next first move. Subscribe to our Patreon show Cohosts for Life for weekly bonus epi...
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 find clarity, busts a few big healing myths, and shares why fear has been one of her greatest teachers...
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 relationship status, the confusing space of wanting a relationship but knowing it might not quite fit ...
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 wedding, what our plans are for what's to come, and more. If you love this episode and want to support ...
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. Subscribe to our Patreon show Cohosts for Life for weekly bonus episodes from me and Jake! Book a 1:1 dati...
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 work—therapy, growth, reflection—and still not finding it. She shares how her family became her villag...
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 that doesn’t need someone to complete it—just someone to add to it. Try Housework with their 2-for-1 ...
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 you’ve ever felt stuck, triggered, or like you lost yourself in love—this one’s for you. Meg shares what i...
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. We get into the messy, emotional side of weddings: cold feet, pre-wedding panic, and what it really mea...
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 about the five Human Design types and how each one tends to show up in dating, why we’re drawn to certa...
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 from a listener. We dive into a listener question about food sharing, discuss dating with food alle...
I’m joined by Melissa Fitch and Michelle Unger, the BFF duo behind The M Take pod. They’re both married to their long-time loves (a college boyfriend and a high school sweetheart!) and navigating motherhood, partnership, and friendship together. We dive into what they wish they talked about before getting married or pregnant, and how becoming parents at different times affected their friendship. Melissa opens up about feeling disconnected when Michelle was pregnant and she wasn’t, and how they f...
I’m joined by Eli Weinstein, LCSW, therapist and host of The Dude Therapist Podcast, for real talk about what women often misunderstand about men, the pressure to be emotionally “on the same level” in relationships, and how to approach hard conversations with care. We also get into the overload of self-help content online, what to watch out for, and how to stay grounded in your growth—even if your partner isn’t quite there yet. Eli also answers some thoughtful listener questions about dating, s...
In this solo episode, I’m sharing some unexpected life updates—including a few medical things I’ve been navigating lately—and TV shows I recently found out not everyone has seen (which feels criminal, honestly). Then we’re diving into modern dating red flags that are actually... green. From not texting all day to taking things slow to living at home and not having social media, there are a lot of behaviors we’ve been taught to panic about that are actually signs of emotional maturity, intentiona...
I’m joined by Benjamin Camras, Flirt Coach and host of Flirtations!, to talk all things flirting—how to build real chemistry, flirt without the ick, and actually know when someone’s into you. We answer your questions about navigating workplace crushes, why great text chemistry can fall flat in person, what it means when you keep getting the “just friends” response, and how to flirt with confidence (even if you’re socially anxious). Whether you love flirting or dread it, this episode has somethin...
I’m joined by my childhood best friend Jessie — the one who’s seen me through every confusing situationship, career pivot, and major life change. We’re talking about how she went from friends to married with her high school crush, what it was like when the three of us lived together, and her take on the guys I used to date… versus what she thought when she met Jake. We also answer listener questions about being in different life stages than your friends, falling for a friend, and how to support ...
Author and Relationship Expert Dr. Morgan Cutlip joins me to unpack the invisible load we carry in relationships—why emotional and mental labor often falls on one partner, and how to create more balance without resentment. We also talk about how relationship needs shift from dating to marriage, how to spot self-sabotage, and why independence can be hard to let go of in your first serious relationship in your 30s. Whether you’re single, dating, or deep in a long-term relationship, this episode wi...
Cohosts for Life is our new Patreon weekly series where we (Ilana & Jake) sit down every Sunday—just the two of us—to reflect, laugh, vent, and share the real behind-the-scenes of our lives together. Think of it as our relationship diary, marriage memoir, and life update all wrapped into one cozy, chaotic, honest little episode that drops every Monday. Whether we're unpacking what made us laugh this week, sharing stories we forgot to tell each other in real time, or navigating the growing pa...
At 27, Alanna Vizzoni was diagnosed with breast cancer—and everything changed overnight. In this raw and honest conversation, she opens up about what it was like to go from “normal” to navigating chemo, a mastectomy, and a surprise engagement all in the same chapter. We talk about identity, body image, intimacy, and what it means to love and be loved through something life-altering. Alanna shares the moments that broke her, the ones that brought her closer to herself and her partner, and why she...
In this episode, I sit down with Emma Paige, host of 'too much.', to explore the twists, turns, and personal growth that led her to the love of her life. Emma opens up about her journey from LA to New York, the heartbreaks that shaped her, and how a chance meeting turned into something real with her boyfriend, Mr. Right. We dive deep into what it really takes to move on from relationships that aren’t serving you, why being too much is subjective, and why friendship breakups can be just as heartb...
In this solo catch-up, I’m giving you a life and mindset update from changing my Instagram handles to finally breaking through a running plateau that had me feeling stuck for months For the heart of the episode I share how pouring into activities outside of work, social media, and my relationship transformed my anxiety into confidence. I break down how hobbies helped me learn to like myself again—and why that made my relationship with myself and Jake even stronger. Plus, I answer some of your ju...
Carleigh Ferrante from the Mostly Dating Podcast is back again to discuss the joys and challenges of dating, relationships, and growing into yourself. We talk about how creative date ideas can deepen connection, why maintaining individuality in relationships is essential, and how navigating different life timelines doesn’t have to create distance between partners. We unpack the importance of open communication, embracing change, and staying grounded in who you are—even in love. Follow @mostlydat...
In this episode, I sit down with executive coach and author Keren Eldad to explore how the same perfectionism and overachievement that drive success can also sabotage our relationships. We discuss the trap of seeking external validation in dating, how people-pleasing can lead to unfulfilling connections, and why high achievers often struggle with vulnerability and intimacy. Keren shares powerful insights on breaking free from the need to "perform" in love, embracing authenticity, and building re...
In today's episode, our anonymous guest from Louisiana shares the intense and tumultuous story of his longest relationship, which lasted four years. What begins as a typical college romance soon takes a series of shocking turns, uncovering dark family secrets, emotional turmoil, and betrayals that test the limits of trust and love. From unsettling revelations about his ex-girlfriend's upbringing to the jaw-dropping discovery that her previous boyfriend was actually her step-brother, this story i...
I sit down with author, podcaster, and relationship coach Allison Raskin for a raw and insightful conversations about love, heartbreak, and moving forward. Allison opens up about her broken engagement that left her blindsided—and how she rebuilt her life, redefined her self-worth, and unexpectedly found love again.We discuss why some breakups feel impossible to move on from and how overthinking can impact relationships. Allison discusses the biggest mistakes people make in dating and how to brea...
Time for a solo episode! ’m catching up with you on everything that’s been on my mind—dating, friendships, and some personal struggles I’ve been working through. I dive into defining the relationship, why second thoughts in dating are totally normal, and how to overthink a little bit less. Book a 1:1 dating coaching session or profile revamp with me here Get $10 off your Nutrafol subscription at nutrafol.com promo code SEEINGOTHERPEOPLE Give yourself the luxury you deserve + free shipping & ...
