Seeing Other People

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...

Amy Chan returns to Seeing Other People five years after her first appearance to talk about her new book UNSINGLE and what it actually takes to create a healthy, lasting relationship. We talk about why so many of us keep repeating the same dating patterns, how we're often optimizing for the wrong things, and why chemistry alone isn't enough to build something long-term. Amy shares her “dating funn...

We're back with Ilana's LA trip recap, a lot to be grateful for, and two listener questions that made us cry. Ilana returns with two unhinged stories — a barista who said something unhinged to every customer and a saleswoman who congratulated someone on a pregnancy that was very much not happening. We answer a question from a 28-year-old in NYC who's trying not to be bitter about being single, and...

Ryan is a 43-year-old single dad living in a small coastal town in Mississippi, navigating dating with a uniquely small dating pool — and a clear idea of what he wants. After two divorces, gaining full custody of his kids, and years focused on raising them, he’s now approaching life as an empty nester and ready to find a partner. In this Unfiltered episode, Ryan shares what it’s like dating long-d...

After going on 150 dates with 60+ people in 10 months, Talia Koren didn’t expect to meet her husband when she did, especially because he wasn’t her type, didn’t give instant sparks, and entered her life while she was still dating other people. In this episode, Talia shares how dating intentionally and treating dating like a research experiment helped her move on from a six-year relationship, stop...

Jake and I catch up on the abandoned 20-week challenge, our first jobs out of college, and a post-wedding brunch we hosted that actually came together really well. Then we tackle a listener question from someone who accidentally went on a Hinge date with her casual boyfriend's friend's roommate (New York City is a very small village), and help her figure out how to have the exclusivity conversatio...

Trigger Warning: This episode includes discussions of emotional abuse, control, isolation, and trauma. In this Unfiltered episode, an anonymous guest shares her experience entering her first relationship at 15 — and how what started as support during a vulnerable time slowly turned into control and isolation. She opens up about the red flags that appeared over time, losing contact with friends and...

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...