Seeing Other People

Ali from Finding Mr. Height is back, and this time she’s sharing the story of how she finally met her boyfriend. After years of dating app burnout and multiple first dates every week, she decided to try something different, showing up to real-life events with zero expectations, and one night she almost skipped ended up changing everything. In this episode, we talk about how she met her boyfriend u...

This week’s Cohosts for Life , we’re diving into some of your best (and most layered) listener questions yet. From navigating dating while dealing with a potential job loss, to figuring out what to do when a close friend slowly fades out of your life, we’re giving our honest, unfiltered advice. We also talk about family dynamics, what to do when your partner isn’t putting effort into relationships...

In this episode, I’m joined by Dana Joy, host of Not That Deep, to talk about sober dating, letting go of pressure, and why modern dating doesn’t have to be so complicated. Dana shares how stopping drinking changed the way she approaches dating, why coffee and walk dates feel more intentional, and how shifting to an "it's not that deep" mindset helped her stop overthinking every interaction. We al...

In this episode, I’m joined by Andie P, creator of Ask a Fuckboy, to break down mixed signals, emotional unavailability, and the behaviors that leave you confused in modern dating. We talk about the difference between a fuckboy and someone who’s just not that into you, translating common “fuckboy” texts, why even smart people fall for mixed signals, when to communicate versus walk away, how techno...

This week we’re catching up on everything from a very full week, including a Boys Like Girls concert, Ilana’s new sewing hobby, and Jake questioning whether anyone actually needs to know how to spell anymore. We get into a listener follow-up about not liking the person you’re dating’s friends and what it actually means if they act differently around them. We also answer a question about moving cit...

After reconnecting with her high school sweetheart years later, this anonymous guest believed she had found the love that was always meant to be. But what followed was a three-year relationship filled with emotional neglect, anxious attachment, resentment, and a version of herself she barely recognized. In this unfiltered conversation, she shares how unresolved grief, abandonment wounds, and mixed...

Life happens, and when it does, how you respond can change everything. In this episode, Dr. Rachel returns to talk about her new book When Life Happens, and why small, intentional shifts, not major life overhauls, are often what create the biggest change. We talk about dating burnout, confidence, body image, reacting vs. responding to stress, and why connections don’t always spark instantly. Dr. R...

On this week's Cohosts for Life episode, we're answering your dating questions and talking through some of the situations that come up when you’re getting to know someone. We get into everything from communication to overthinking to figuring out what actually matters early on. We also share your dating wins, from putting yourself out there to big relationship milestones. ALL links here (submit a Q...

After years of dating, heartbreak, and learning what she truly needed in a partner, Jess shares how she finally met the man she hopes to marry at 42. From relationships that lacked communication, to staying too long in something that wasn’t right, to navigating health challenges and dating later in life — every chapter led her to a slow-burn connection through matchmaking. ALL links here (submit a...

In this episode, I’m joined by Therapist and Secure Attachment Coach Trevor Hanson to breaks down what anxious attachment really looks like in dating—and why feeling “not enough” can quietly shape your relationships. We talk about self-sabotage, chasing emotionally unavailable partners, and how to shift from fear to security. If you’ve ever felt unlovable or stuck in patterns you can’t explain, th...

This week we’re talking about Ilana’s half marathon experience and what the race actually felt like compared to training. We get into why running can be such a mental challenge and how expectations going in can shape the experience. Jake shares about his weekend at Mohegan Sun and we talk about gambling, risk, and why it can be so appealing. Ilana also shares her new focus on trying new things, fr...

TW: this episode includes discussion of body image and suicidal thoughts. Please take care of yourself and only listen if you feel safe doing so. In this deeply honest episode, a returning anonymous guest opens up about living and dating with long-term body image struggles as a man. From childhood bullying to the realities of dating apps, he shares how external judgment has shaped his confidence,...

In today’s solo Q&A, I’m answering your real, messy, specific dating questions. We’re talking about red flags vs. anxiety, high standards, situationships, giving too many chances, and that weird feeling when your friends don’t like him. I also get into spark vs. stability and how to stop spiraling about your timeline. If you’ve ever wondered am I self-sabotaging or am I settling, you’ll want t...

This week we’re sharing some of our relationship hot takes and debating a few modern dating questions couples don’t always agree on. We talk about things like whether it’s ever okay to look through your partner’s phone, sharing phone passwords, sharing locations, and whether having crushes on other people is normal. Then we play a blind ranking game where we rank different third date ideas without...

A 36-year-old single woman shares the reality of modern dating: a year-long casual situationship, dating app fatigue, and the pressure of watching younger siblings get married while you’re still searching for your person. We talk about what it’s like designing engagement rings while being single, the aftermath of a toxic long-term relationship, and the unexpected lessons from group therapy. From m...

Misha Brown joins the podcast to talk about her book Be Your Own Bestie and the real work behind learning to like yourself. We discuss why being a good friend to others starts with being a good friend to yourself, the pressure to shrink ourselves, and how shame shapes the way we move through life. Misha shares her SaaS method for building confidence, the power of “dating yourself,” and why small d...

This week we’re back from Hawaii and immediately thrown into jet lag, daylight savings, and the reality of jumping straight back into work. We talk about how quickly vacation mode disappears once the Sunday scaries hit and real life starts again. We recap some of our favorite moments from the trip, including playing with baby animals and exploring fruit farms in Kauai. Ilana shares some big news a...

I thought I was the exception to the dating advice everyone gives when you’re single. I wasn’t. In this episode, I’m breaking down the advice I ignored and what it cost me, from chasing potential to confusing mixed signals for chemistry. We’ll talk about desperation, fixing people, and the stories we tell ourselves to avoid walking away. If something feels off in your relationship, this might help...

Eli Weinstein⁠ returns to the pod fresh off releasing ⁠From I Do to We Do⁠ , and we’re getting real about what actually makes relationships work — long before kids enter the chat. We talk about the biggest mistakes people make while dating, the underrated green flags that matter for the long game, and why most couples don’t blow up overnight… they just never had the hard conversations early on. El...

This week we’re recording from Hawaii and reflecting on the trips we’ve taken together, from our first weekend away to big family vacations. We talk about how travel reveals your real relationship dynamic, what happens when you start merging families, and why in-law situations can feel simple for some couples and complicated for others. We also get honest about shared PTO, family expectations, and...

Caroline Sacks joins the pod to break down her Hinge meet-cute turned long-term love story — from casually dating in NYC to defining the relationship months later. We talk about dating without intention (and getting lucky), being the “boyfriend girl,” and why marrying with intention matters more than dating with it. She opens up about choosing a calm partner over chemistry chaos, navigating conten...

I’m joined by Colette Jane Fehr , couples therapist, relationship expert, and author of The Cost of Quiet: How to Have the Hard Conversations That Create Secure, Lasting Love. We talk about why “not fighting” isn’t the same as being connected, how losing your voice can slowly erode a relationship, and what it actually means to do the work in love. Colette shares how her own divorce, dating experie...

This week on Co-Hosts for Life, we’re catching up on work offsites, falling off our 20-week challenge, and the half marathon I secretly signed up for that got canceled, so I ran it alone anyway. I share why I needed that race for myself and how it ended up being one of my strongest runs ever. Then we answer your questions about supporting a friend through a breakup, losing the “obsessed” feeling i...

In Part 2 of my career story, I’m picking up right where we left off — from losing my job at Hinge to launching Seeing Other People just weeks later. I break down how the podcast actually grew, why co-hosting didn’t last, and what it really looks like to make money as a podcaster, content creator, and dating coach. I get radically honest about freelancing, brand deals, influencer income, pay trans...

We’re recapping an unforgettable weekend in London celebrating Jake’s brother Jeff and his now-fiancée Sydney’s engagement. We talk about the behind-the-scenes chaos of keeping the surprise secret, tracking them on Find My Friends, dodging FaceTime calls, and the moment everyone ran out to surprise them. We also catch up on our 20-week challenge struggles, Ilana’s mortifying podcast scheduling mis...