Seeing Other People

I’m joined by my friend Emily Griminger to talk about dating in your 30s when your life doesn’t look the way you thought it would. Emily shares how leaving the corporate world to start her own company changed the way she dates, what it’s been like navigating weddings and big milestones without a partner, and why being on a different timeline than her friends has forced her to get more honest about...

I’m joined by Dr. Courtney Alexander , OB-GYN and women’s health expert, to break down what women actually need to know about fertility, birth control, and reproductive health in their 20s and 30s. We talk about the biggest myths fueling anxiety around age, timelines, and “falling behind,” and why so much of the information online is doing more harm than good. Dr. Alexander explains what fertility...

Jake and I kick things off with life updates, including his big winnings at the casino, an influencer event I actually enjoyed, a running injury update, and a Taylor Swift debate. Then we get into listener questions about dating when conversations feel one-sided, wondering if you’re being too picky on early dates, and what to do when you end things with a genuinely nice guy and immediately regret...

Maddy, friend and former SOP intern, joins the pod to talk about surviving a break-in, navigating trauma in your early 20s, and how EMDR therapy helped her finally feel safe again. Maddy opens up about the night a man broke into her bedroom, why healing wasn’t as simple as “moving on,” and how hypervigilance shaped her day-to-day life, dating, and friendships. We get into how how meeting someone w...

I’m joined by Emily Durham , recruiter, creator, and host of Clock In , to talk about the surprising overlap between careers and dating in your 20s and 30s. Emily shares how leaving corporate shifted the way she dates, why confidence at work affects confidence in relationships, and the patterns she sees in both job searches and love lives. We get into the pressure of wanting to be chosen, the fear...

Jake and I catch up on life and our ongoing messiness at home before getting into a really honest conversation. I talk about seeing other podcasts share huge numbers and noticing my own growth has slowed, and how hard it has been not to compare myself. I also share what success feels like to me right now and how I am trying to build a career that still feels good even when the numbers get in my he...

I’m joined by my friend Jude Cohen to talk about dating in your 30s and rebuilding your life after everything falls apart at once. Jude shares how losing her job and leaving the corporate world completely shifted the way she dates and sees herself. We get into her best and worst dating stories, from Third Date Club to a friends-with-benefits situation that actually worked to the first-date disaste...

I’m joined by Alyssa Tucker, teacher, creator of @livefromsnacktime , and mom of two, to share her unexpected journey through infertility. After years of loss and failed IVF transfers, Alyssa and her husband pursued surrogacy, only for her to discover she was pregnant at the same time. We talk about IVF misconceptions, how surrogacy actually works, and what it was like to welcome two babies just s...

We're recording from Westchester while recovering from days of Thanksgiving meals and leftovers. We talk about having both of our families together for the first time and how grateful we are that everyone gets along so well. Jake shares an update on his injury, and we chat about supporting each other’s plans and giving each other space. We answer listener questions about mixed signals, married men...

In this Unfiltered, Harry comes back to talk about what dating, healing, and growing in your mid thirties has actually looked like for him this past year. We get into how friendships shift as everyone around you moves into new phases of life, what it feels like to be the single one in the group, and how he has learned to sit with discomfort instead of running from it. He shares how hobbies and com...

I’m joined by Dr. Tracy Dalgleish, couples therapist, author of You, Your Husband, and Your Mother-in-Law, and host of Dear Dr. Tracy, to dive into the messy and emotional dynamics of merging families. You don’t have to be married for this to resonate; these patterns show up in every relationship, and every couple can benefit from understanding them. We break down the biggest myths about in-laws,...

We’re on week 3 of lockdown after Jake’s surgery and shockingly, we’re thriving. This week marks five years since we both got let go, so we’re diving into what those last few months looked like, what we felt in the moment, and how getting fired ended up being the turning point we didn’t know we needed. For the first time, I open up about why I was crying everyday during my last few months at Hinge...

In this Unfiltered, a returning guest shares how she finally got over her ex and why getting under someone else wasn’t the whole story. After leaving a five-year relationship, she had to rebuild her confidence, rethink her standards, and figure out who she was without him. She opens up about dating again in her 30s, friendship shifts, loneliness, and the moment she realized she no longer cared wha...

Therapist Rebecca Marcus, LCSW, is back to talk about what it actually means to “do the work” in your love life. We unpack why awareness alone isn’t enough to break old patterns, how to tell the difference between real growth and just performing self-improvement, what to do if you’re doing everything “right” but still feel lonely, and whether it’s possible to over-communicate to the point it kills...

I’m fresh off a total bucket list moment, going back to Syracuse to speak at the launch of their new Center for the Creator Economy, and I’m bringing you along for the whole thing. I also share some big news with Jake live on the podcast, and his reaction does not disappoint. Jake talks about not leaving the apartment for 11 days after his surgery, and we reflect on the kind of support you sometim...

In this solo Q&A, I’m answering your dating and life questions — from moving cities for love to figuring out if you’re settling in your career. We get into what to do when your best friend disappears into a new relationship, how to tell if someone actually likes you, and the truth about not having it all figured out at 29. I also share my thoughts on wedding planning stress, dating apps, and w...

Kelly Chase (@chaselifewithkelly) opens up about what really happened after Love Is Blind, the trauma, the healing, and how she learned to love herself again. From people-pleasing to personal growth, she shares how therapy, mindset coaching, and deep self-work helped her rediscover her worth. We talked about rebuilding after being misunderstood, reclaiming your story, and learning to date yourself...

Jake’s been recovering from surgery with nonstop movie marathons, while I got upsold by a facialist and found myself spiraling about Botox because everyone around me seems to be doing it. I’m also on the hunt for a new hobby now that my running era has ended (open to suggestions). This week, I’m heading up to Syracuse to speak on a college alum panel (!!). Plus, we’re diving into the viral British...

Heidi Friedman (@lovelessons104) went on 104 dates before finding the love of her life — and every single one taught her something new. A divorced mom of two (and now a bonus mom of two more), she opens up about realizing she was never truly in love with her ex-husband, rebuilding her confidence, and finally finding the kind of love she used to only hear about. We talk about what real love actuall...

I trained for months dreaming of the NYC Marathon finish line… and instead found myself sitting on the side of the course having a panic attack at mile 6. In this episode, Jake and I break down everything — from the logistics and the high of those first few miles, to the moment everything changed, why I kept going, and what I learned from one of the hardest days of my life. Jake also shares what t...

Most of us never learned how to talk about sex—so we assume everyone else just figured it out. Sex therapist Vanessa Marin and her husband Xander Marin join me to talk about what really makes intimacy last, why communication in the bedroom matters more than chemistry, and how to start conversations about sex before it becomes a problem. We dive into the myths that make us feel broken, how to keep...

Dating advice is everywhere, but most of it is useless. From ghosting after a “perfect” date to why playing hard to get always backfires, Logan Mahan—writer of Take It From a Woman at InsideHook—shares what women actually want, the mistakes men don’t realize they’re making, and the small shifts that can completely change your dating life. Follow Logan on Instagram @loganspants ALL links here (dati...

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 bet...

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 T...

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...