Seeing Other People

In this raw and emotional follow-up to I Didn't Expect This Relationship to Break Me , an anonymous guest returns to share the final chapter of her story—and the moment she finally found the strength to walk away. After years of broken promises, emotional neglect, financial strain, and a relationship that left her feeling increasingly disconnected from herself, she opens up about what kept her stu...

Brandi Davis ( @backpocketcounseling ) joins the podcast for a deep dive into modern dating, relationship anxiety, communication, attachment styles, and the patterns that keep us stuck. As a licensed marriage and family therapist and founder of Back Pocket Counseling, Brandi shares why so many people feel exhausted by dating, how social media fuels comparison and self-doubt, the signs of emotional...

We're recording at the earliest time ever — Friday morning, two broken water dishes deep, and heading into an absolutely stacked weekend (a wedding, two baby showers, a birthday, and Father's Day). We run through a round of dating debates and would-you-rathers — who should text first after a date, is it ever okay to snoop, can you be best friends with an ex — before getting into two listener quest...

At 25 years old, this anonymous guest has never been in a serious relationship—and while she knows she's not alone, it often feels that way. In this unfiltered conversation, she opens up about watching friends get engaged while she's still navigating first dates, the pressure of feeling "behind," and the self-doubt that comes from wondering why love hasn't happened yet. We talk about health strugg...

Julie LaPlaca joins the podcast to share her journey from longtime producer on the Bachelor franchise to author of The Love Producer. We talk about what really happens behind the scenes of reality dating shows, how helping others find love impacted her own relationships, why she walked away from her dream job, and the self-discovery journey that followed. Plus, we discuss vulnerability, hypnothera...

The Knicks are champions and Jake may have cried a little. We start there. Then four listener questions: whether therapy actually helped Ilana find Jake (yes, and here's how), how to tell the difference between giving someone grace and making excuses for them, whether having a great life alone means you're too independent to be in a relationship, and the big one — he's kind, emotionally available,...

Cara Ozek joins the podcast for a conversation about confidence, dating, and the small changes that can have a big impact. From style, grooming, body language, and dating app profiles to dating burnout, feedback, and self-growth, Cara shares how helping friends show up as their best selves inspired her own journey. We also talk about meeting people in real life, overcoming the fear of social event...

Addie Sellers joins the podcast to share one of the most shocking experiences of her matchmaking career: working with a client who was later convicted and sentenced to 80 years in prison. We talk about the subtle red flags people miss in dating, why trusting your gut matters, how predators can hide behind seemingly perfect reputations, and the lessons Addie learned that changed the way she approac...

Happy Monday! We're recording from Jake's childhood bedroom fresh off a wedding the night before. We talk about why we're obsessed with vows and speeches, what it's like to hear other couples' love stories and reflect on your own relationship, and the text a maid of honor read aloud that had us wanting to dig through our own phones. Then we get into our main segment: a fun game of red flags and de...

This solo episode is all about hindsight, growth, and the dating choices I understand differently now. I’m reacting to listener-submitted scenarios through two lenses: what past me probably would’ve done, and what I’d do now. We’re talking about emotionally unavailable people, confusing anxiety for chemistry, trying to be chosen instead of evaluating compatibility, and the difference between knowi...

Lauren Makler joins the podcast for a conversation about fertility anxiety, egg freezing, dating pressure, and the emotional weight so many women carry around timelines. From AMH testing and IVF to secondary infertility, miscarriages, and dating in your 30s, we talk about the difference between making empowered decisions versus fear-based ones. Lauren also opens up about her own rare disease diagn...

 Happy anniversary to us — we're recording this one from Miami in the hotel where we took our first trip together five years ago. Jake planned the whole thing, and we almost missed the flight (not our fault!). We get into the debate that started at the airport: are you still on your parents' phone plan in your 30s? Four listener questions this week: the guy who followed you on Instagram two y...

Allison Lane joins the podcast for a conversation about dating in your 30s, meeting people in real life, and the pressure women feel to have everything figured out by a certain age. From run clubs and dating apps to confidence, friendships, and navigating New York City single, we talk about what it actually looks like to put yourself out there without romanticizing every interaction. Allison also...

Dr. Joy Burkheimer joins the podcast for a conversation about second chances, relationship “redemption arcs,” and whether people can actually change after hurting someone they love. From attachment styles and cheating to avoidant behavior, breakups, and the psychology behind going back to an ex, we talk about the difference between genuine growth and simply saying the right things. Dr. Joy also op...

We're both sick, we slept until noon, and we have a mystery anniversary trip in two days — Jake planned the whole thing and Ilana has no idea where they're going. We talk froyo orders (gummy bears are a crime), the great do-guys-actually-give-each-other-style-feedback debate, and tease next week's recording from wherever they end up. Two listener questions this week: one from someone whose relatio...

For so much of my life, I thought certain milestones would fundamentally change me. The relationship, the career growth, the apartment, the race finish line, the goals I spent years chasing. I thought I’d feel more confident, more secure, more fulfilled once I finally got there. But lately, I’ve been realizing how no achievement permanently changes your internal world the way we expect it to. In t...

Chloe Hechter joins the podcast for a conversation about everything your twenties are actually filled with: changing career paths, feeling behind, navigating dating in New York City, and learning how to stop centering relationships as the main goal. From growing up as a New York theater kid to switching majors in college, going viral online, and finding confidence after years of feeling “too much,...

Ilana's recording this one from her deathbed after missing the Brooklyn Half and sleeping the weekend away while Jake walked 25,000 steps to get a burger. Two listener questions this week: a woman who met a guy in Ireland, and booked another trip at his request, and he canceled two weeks out saying he doesn't want long distance — and a woman who got ghosted before a second date, redownloaded the a...

Meg Reynolds is back and we get real about what your twenties actually feel like—uncertain, uncomfortable, and constantly shifting. From turning 27 and questioning everything to navigating dating, friendships, and career paths that don’t look how you expected, this is a conversation about letting go of timelines and figuring it out as you go. ALL links here (submit a Q, pitch yourself to the pod,...

This week, I’m joined by content creator Annie Jorgensen to talk about what really shifts when you turn 30 and stop looking for someone to complete you. From a major heartbreak (with a cheating ex who had already bought a ring) while all her friends were getting engaged, to rebuilding her confidence and completely changing how she dates, Annie shares how she went from dating for validation to actu...

Jake's back from Florida with a roulette win and some bachelor party receipts. Ilana has a major life announcement that's been months (or years) in the making.. Two listener questions: does astrology actually matter in dating, and how do you stop waiting for the other shoe to drop when something finally feels really good? ALL links here (submit a Q, pitch yourself to the pod, dating coaching &...

In this episode, we sit down with Kerry Russo, the creator behind UES Things, to talk about what it actually means to put yourself out there — and why staying in your comfort zone might be the biggest thing holding you back in dating and life. From meeting people in real life to going to events alone, starting conversations, and doing things that feel uncomfortable at first, this conversation is a...

Trevor Hanson is back for part two, and this episode goes even deeper into people pleasing, anxious attachment, and what it really means to feel secure in yourself. We talk about why even secure people can feel anxious in certain relationships, how to stop abandoning yourself to keep others happy, setting boundaries without guilt, and how identifying your values can completely change the way you d...

Jake's heading to Fort Lauderdale for a bachelor party with zero itinerary and a plan that's basically "watch the Knicks, find a Chili's." We kick things off comparing how differently men and women plan these trips, and it's not even close. We tackle a listener question about bachelorette party costs spiraling out of control and how to set a boundary without being labeled unsupportive. Then, A lis...

Juliette Haas is about to leave a life that works — great friends, a solid routine, and NYC exactly as she always imagined it — to move to London anyway. In this episode, we get into what it really means to choose discomfort on purpose, from solo traveling for the first time to realizing she didn’t want to be the person who only talks about doing things. We talk about growing up online, unlearning...