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 This and the parallels between the couples on the show and our own relationship. Listener questions include handling a partner who hasn’t said “I love you” yet and believing good guys are still out there.

ALL links here (dating coaching, profile revamp, marathon fundraiser, and more!) 

Get $10 off your Nutrafol subscription at nutrafol.com promo code SEEINGOTHERPEOPLE

Stock up on the best elevated essentials + get free shipping & 365 day returns at Quince.com/seeingotherpeople 

Get 25% Off @CowboyColostrum with code SEEINGOTHERPEOPLE at www.cowboycolostrum.com. #CowboyColostrumPod 

Your mental health matters. Head to rula.com/seeingotherpeople to connect with a licensed therapist who truly cares

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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 (dating coaching, profile revamp, marathon fundraiser, and more!) 

Get $10 off your Nutrafol subscription at nutrafol.com promo code SEEINGOTHERPEOPLE

Stock up on the best elevated essentials + get free shipping & 365 day returns at Quince.com/seeingotherpeople 

Get 25% Off @CowboyColostrum with code SEEINGOTHERPEOPLE at www.cowboycolostrum.com. #CowboyColostrumPod 

Your mental health matters. Head to rula.com/seeingotherpeople to connect with a licensed therapist who truly cares

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Dr. Molly Burrets called off her own wedding—and it changed everything. She shares the story of what led her to make that difficult decision, the self-reflection and work she realized she needed to do afterward, and how she eventually married the love of her life. We dive into the fear of shame and embarrassment that often comes with calling off a wedding—and why the reality is often far more supportive than you might expect. Molly also breaks down how to tell if your doubts are coming from anxiety or intuition, and walks through the key questions you should ask yourself if you’re unsure about ending a relationship.Whether you’re engaged, in a long-term relationship, or just curious about navigating big emotional decisions, this episode is full of practical guidance and compassionate insight. Follow Dr. Molly at @drmollyburrets and learn more at www.drmollyburrets.com

ALL links here (dating coaching, profile revamp, marathon fundraiser, and more!) 

Get $10 off your Nutrafol subscription at nutrafol.com promo code SEEINGOTHERPEOPLE

Stock up on the best elevated essentials + get free shipping & 365 day returns at Quince.com/seeingotherpeople 

Get 25% Off @CowboyColostrum with code SEEINGOTHERPEOPLE at www.cowboycolostrum.com. #CowboyColostrumPod 

Your mental health matters. Head to rula.com/seeingotherpeople to connect with a licensed therapist who truly cares

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Jake and I are back reflecting on how good it feels to be surrounded by reliable people, the upgrades we’ve made to our apartment, and all the business ideas we’ve had but never acted on. Then we get into the big questions: did dating apps actually make dating easier or just more exhausting? Are you even allowed to date someone who’s allergic to your favorite food? We compare the best and worst parts of being single versus being partnered, and wrap with a wild “Am I The Asshole?” listener scenario involving a self-destructive friend who hooked up with another friend’s boyfriend.

ALL links here (Submit a Q, schedule a call with me, marathon fundraiser, and more!) 

Get $10 off your Nutrafol subscription at nutrafol.com promo code SEEINGOTHERPEOPLE

Stock up on the best elevated essentials + get free shipping & 365 day returns at Quince.com/seeingotherpeople 

Get 25% Off @CowboyColostrum with code SEEINGOTHERPEOPLE at www.cowboycolostrum.com. #CowboyColostrumPod 

Your mental health matters. Head to rula.com/seeingotherpeople to connect with a licensed therapist who truly cares

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

I’m joined by Judit, a 49-year-old woman living in Barcelona who has never been married and is opening up about what it’s really like to be single at this stage of life. She shares what she wishes she could tell her 30-year-old self about dating, how the landscape has shifted from pre-apps to today, and how she responds when people ask, “why are you still single?” Whether you’re panicking in your late 20s or feeling the pressure in your 30s, this conversation is a powerful reminder that timelines are made up and there’s more than one path to happiness. Follow Judith on IG @it.is.miranda.time and grab a copy of her book https://natodating.com/

ALL links here (dating coaching, profile revamp, marathon fundraiser, and more!) 

Get $10 off your Nutrafol subscription at nutrafol.com promo code SEEINGOTHERPEOPLE

Stock up on the best elevated essentials + get free shipping & 365 day returns at Quince.com/seeingotherpeople 

Get 25% Off @CowboyColostrum with code SEEINGOTHERPEOPLE at www.cowboycolostrum.com. #CowboyColostrumPod 

Your mental health matters. Head to rula.com/seeingotherpeople to connect with a licensed therapist who truly cares

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

If you’ve ever stressed about your biological clock or worried what your future fertility might look like, this episode is for you. I’m joined by Kirsten Karchmer, a reproductive health expert who’s worked with over 10,000 couples through infertility and founded Conceivable to make care more effective and accessible.We talk about the signs in your cycle you shouldn’t ignore, what you can start doing now—before you even have a partner—to support your fertility, and how stress, relationships, and self-advocacy all play a role. Kirsten’s advice will leave you feeling informed, empowered, and more in control of your future.

https://conceivable.com/

https://www.tiktok.com/@yourfertilityexpert

https://www.tiktok.com/@theperiodexpert

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Ciao! We’re back from Italy and breaking down the highlights! Jake crushed it on the golf course while I ate spaghetti pomodoro every single day with no regrets. We talk about bringing your partner on a family trip, being creatures of habit, and then dive into your answers to my Instagram polls. If a relationship feels good but something is missing, is that enough to leave? Would you date someone who checks every box but doesn’t excite you? Are you settling without realizing it? We read your submissions and debate which hit home the most.

ALL links here (submit a Q, dating coaching, profile revamp, and more!) 

Get $10 off your Nutrafol subscription at nutrafol.com promo code SEEINGOTHERPEOPLE

Stock up on the best elevated essentials + get free shipping & 365 day returns at Quince.com/seeingotherpeople 

Get 25% Off @CowboyColostrum with code SEEINGOTHERPEOPLE at www.cowboycolostrum.com. #CowboyColostrumPod 

Your mental health matters. Head to rula.com/seeingotherpeople to connect with a licensed therapist who truly cares

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this solo episode, I get vulnerable about a big life change I’m going through and what it’s teaching me about growth, and timing. I break down two listener scenarios: one from someone in a long-term relationship wondering if they’re settling because the spark feels missing, and another from a single listener questioning whether to lower their standards or stay single while searching for someone who truly excites them. We unpack the difference between healthy standards and unrealistic checklists, attraction versus compatibility, and how to trust yourself when it comes to matters of the heart.

ALL links here (dating coaching, profile revamp, marathon fundraiser, and more!) 

Get $10 off your Nutrafol subscription at nutrafol.com promo code SEEINGOTHERPEOPLE

Stock up on the best elevated essentials + get free shipping & 365 day returns at Quince.com/seeingotherpeople 

Get 25% Off @CowboyColostrum with code SEEINGOTHERPEOPLE at www.cowboycolostrum.com. #CowboyColostrumPod 

Your mental health matters. Head to rula.com/seeingotherpeople to connect with a licensed therapist who truly cares

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Conversations with the people we love can feel harder than ever, but small shifts in how we listen and speak can completely transform your connections. I talk with New York Times bestselling author Charles Duhigg (Supercommunicators, The Power of Habit) about how to navigate tricky conversations, build trust, and create deeper connection in dating, relationships, friendships, and family.

ALL links here (dating coaching, profile revamp, marathon fundraiser, and more!) 

Get $10 off your Nutrafol subscription at nutrafol.com promo code SEEINGOTHERPEOPLE

Stock up on the best elevated essentials + get free shipping & 365 day returns at Quince.com/seeingotherpeople 

Get 25% Off @CowboyColostrum with code SEEINGOTHERPEOPLE at www.cowboycolostrum.com. #CowboyColostrumPod 

Your mental health matters. Head to rula.com/seeingotherpeople to connect with a licensed therapist who truly cares

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Live from Italy, Jake and I are recapping the Jewish holidays, what stuck with us from the rabbi’s sermon, and what it was like hosting a holiday for the first time. We’re sharing the highs and lows from our travel day to Puglia, including our very first business class flight and whether we think it’s worth the hype. Then we answer listener questions: what to do when your sister gets engaged while hiding emotional cheating, whether random selfies from someone you're dating signal interest, and if it’s a bad sign when someone goes on vacation and never texts first.

ALL links here (Listener Questions, dating coaching, profile revamp, marathon fundraiser, and more!) 

Get $10 off your Nutrafol subscription at nutrafol.com promo code SEEINGOTHERPEOPLE

Stock up on the best elevated essentials + get free shipping & 365 day returns at Quince.com/seeingotherpeople 

Get 25% Off @CowboyColostrum with code SEEINGOTHERPEOPLE at www.cowboycolostrum.com. #CowboyColostrumPod 

Your mental health matters. Head to rula.com/seeingotherpeople to connect with a licensed therapist who truly cares

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.