Seeing Other People
Dating advice, real stories, and honest conversations about modern relationships. Seeing Other People with Ilana Dunn covers everything from first dates and situationships to long-term love, with expert guests, anonymous confessions, and unfiltered takes three times a week. Whether you're swiping, healing, or somewhere in between...this is your show.
Episodes
What 10,000+ Dating Questions Have Taught Me About Modern Relationships
After reading 10,000+ dating and relationship questions, I've noticed that most people are asking the same thing in different ways: "How do I know I'm making the right choice?" In this solo episode, I'm breaking down four listener questions about anxiety, intuition, dating with intention, relationship doubts, and the pressure to know if someone is "the one." We talk about why modern datin
How to Rebuild Trust When Everything Becomes a Trigger
Therapist and co-host of the Therapy Brothers podcast, Tyler Patrick joins the podcast to share his personal story of addiction, betrayal, recovery, and rebuilding trust after everything fell apart. We talk about why betrayal feels so traumatic, what happens when shame keeps us stuck, how to heal when your nervous system is constantly on high alert, and the difference between surviving a
"All My Friends Are in Relationships and I'm Starting to Feel Left Behind"
Ilana's back on Love Island (long story), Jake played golf four times in eight days, and we're doing absolutely nothing for July 4th and couldn't be happier about it. Three listener questions this week: someone who got blindsided when a guy ended things just one week after they became exclusive — and how not to let it derail you from dating; the reality of being the single friend when all
"How I Finally Left My Toxic Relationship"
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
Why Dating Feels So Hard Right Now (And What to Do About It)
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 emo
Should You Text First? Should You Snoop? We Debate It All.
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 liste
"I'm 25 and I've Never Had a Boyfriend"
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 heal
What Working on The Bachelor Taught Her About Love
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, h
He's Everything I Said I Wanted — But Something Feels Off
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 a
The Reason You're Not Getting a Second Date
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 soc
Matchmaker for a Serial Rapist (Without Knowing It)
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 sh
Red Flags or Dealbreakers? What We'd Think Now vs. When We Were Single
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 fla
My Dating Mistakes I Understand Differently Now
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 betw
Fertility Anxiety, Egg Freezing & Dating Under Pressure
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 dise
All Our Dates Are at His House — Should I Be Worried?
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 Instag
Meeting People IRL, App Burnout & Being Comfortable Being Alone
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. Alli
When a Second Chance Is Worth It (And When It’s Self-Sabotage)
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. Jo
Is It a Red Flag If You Never Fight With Your Partner?
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 whos
I Thought Hitting My Goals Would Feel Different
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
She Thought She Was “Too Much” Until She Met the Right Person
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 “
Stop Waiting for Him to Confirm the Date & Just Text First
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, redownlo
You’re Not Behind, You’re Just in Your 20s
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 t
30, Single, and Happier Than Ever
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 validatio
Waiting for the Other Shoe to Drop & I Have a Big Announcement
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 coachi
Your Next Relationship Might Be Around the Corner
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 conversa
Stop People Pleasing, Start Feeling Secure
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
Bachelor Parties vs. Bachelorette Parties: We Are Not the Same
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.
Meeting Someone When You Least Expect It
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, u
Why You’re Still Single (It’s Not Bad Luck)
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 “da
Should You Keep Dating While Your Mom Is Dying?
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 si
Dating As A Single Dad: Finding Love After Raising His Kids
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 datin
Dating Intentionally: From 150 Dates to Marriage
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 relationshi
"He Found Out I Went on Another Date… Now He’s Acting Weird"
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 co
The Relationship That Turned Into a Prison
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 fr
From Dating Burnout to Meeting The One at 37
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 bo
Dating While Your Life Is Falling Apart + Friendship Drama & Big Life Questions
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 relat
Taking the Pressure Off Dating
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 interacti
Are They a Fuckboy or Just Not That Into You?
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, h
Not Liking Their Friends, Moving For Love and Dating Wins
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 m
"I Didn’t Expect This Relationship To Break Me"
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, a
Life Happens: The Dating Mindset Shift You Didn’t Know You Needed
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 instant
Mixed Signals, Red Flags and Dating Wins
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 (su
"I Found My Life Partner At 42"
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 (
You're Not Unlovable
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 ex
Double Date Ideas, New Hobbies and Taking Risks
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 t
What Dating As A Short Man Is Really Like
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 conf
Am I Asking for Too Much? A Solo Dating Q&A
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’
Relationship Hot Takes & Ranking the Perfect Third Date
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 idea
Dating at 36: Situationships, Dating Apps, and the Pressure to Find “The One”
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 therap
How to Start Showing Up for Yourself
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 wh
Back From Vacation & Spiraling About the Future
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 b
Dating Advice I Ignored (And Regret Not Taking Sooner)
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 m
From I Do to We Do
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 earl
Difficult In-Laws, Shared PTO & Relationship Dynamics
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 expectat
I Stopped Dating My Type and Found My Fiancé
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, navigati
Not Fighting Isn’t the Same as Being Close
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
The Shift, Freedom vs. Stability & My Secret Half Marathon
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”
Career Pt. 2: How I Actually Make Money as a Podcaster & Influencer
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,
We Flew to London for a Surprise Engagement Weekend
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 sched
My “Dream Job” Paid Me $34K and Broke Me: Part 1 of My Career Story
In Part 1 of my career story, I’m breaking down how I got here –from quitting my photojournalism major at Syracuse, to hustling through internships in music, to landing my “dream job” at a major record label that left me underpaid, burned out, and questioning everything. I share what it actually takes to break into creative industries, the realities of pay and privilege, and how burnout a
"Should We Get Married?"
What if loving each other forever doesn’t automatically mean getting married? In this episode, I sit down with Maxson and Emily to talk about their unconventional love story and why they’re questioning marriage instead of rushing into it. We get into prenups, divorce, kids, legal myths, and whether marriage actually strengthens a relationship—or just complicates it.Should We Get Married?
Becoming a Mom at 18 Didn't Stop Me From Living My Life
I’m joined by Jessica Kameko, aka @TravelWithMeko, a full-time travel creator, student, marathon runner, medical esthetician, author, and mom of two. We talk about what her life actually looks like, why she chose to go back to school, what led her to becoming a single mom, and how she’s managed to build a life rooted in travel and flexibility. Then we get into dating as a single mom: how
He Made Valentine’s Day Reservations — Do I Owe Him a Gift?
We’re recording on the eve of our five-year “first date” anniversary and catching up on everything from freezing winter runs and challenge updates to surprise date nights and what it looks like to keep showing up for each other in the small ways. We answer a timely listener question about Valentine’s Day on a fifth date (do you bring a gift or just show up?), talk about dating your frien
When Your Friends & Family Don't Support Your Relationship
I’m joined by my longtime friend Sarah and her husband Ben to talk about what happens when the people closest to you don’t support your relationship. We start with how they met and their very different religious journeys, then get into navigating outside opinions, value clashes, and major life changes while choosing each other anyway. Sarah shares what it was like to trust her own voice w
Losing Yourself in a Relationship and Finding Yourself Again
Author and British Vogue dating columnist Annie Lord joins the podcast to talk about heartbreak, healing, and what actually happens after a long-term relationship ends. We unpack the pain no one prepares you for, why “moving on” isn’t about erasing the past, and how breakups can force massive personal growth. Annie opens up about identity loss, avoidant dating patterns, modern dating burn
All Our Friends Are Moving Away & We're Trying New Hobbies
This week on Cohosts for Life, we talk about being in a season where friends are moving out of the city, buying homes, and stepping into new phases of life, while we’re still in New York figuring out what comes next. We unpack how friendships change with distance, how to stay close when you no longer share a zip code, and the mix of sadness and excitement that comes with watching people m
Going on a GLP1 Changed My (Dating) Life
TW: this episode includes discussion of disordered eating and body image. Please take care while listening. I’m joined by Alana Paris, who opens up about her experience with GLP-1 medications and how the changes to her body have deeply impacted her confidence, dating life, and relationships. We talk about food noise, body image, dating avoidance, navigating vulnerability with new partners
Why Dating Feels Confusing (& What Actually Helps)
In this solo episode, I answer a few listener questions that all point to the same thing: why dating feels so confusing right now. I talk about how to stop hoping potential will turn into effort when someone’s energy changes, how to figure out which dating “rules” actually matter, and how to tell the difference between needing a break from dating and giving up out of burnout. I also expla
Does Our First Date Anniversary Count?
This week on Cohosts, we dive into a debate about which anniversaries actually matter once you’re married. We also answer a listener question about five great dates followed by sudden uncertainty, what it really means when someone says they “need to think,” and how to handle it without spiraling or settling. Plus: social media chaos, internet trends we don’t understand, surprise date plan
How to Stop Dating Burnout and Start Meeting People IRL
Liv Schreiber is back on the podcast, and we’re getting real about dating, love, and connection after the wedding glow fades. From meeting people IRL and surviving dating burnout to choosing the right partner when life gets hard, Liv shares the lessons that actually matter. We talk green flags, why opposites work, and why being yourself beats playing it cool—plus bold takes on weddings, m
What Not Settling Actually Looks Like
In this episode, I’m joined by Sunny, a Syracuse junior who’s doing it all — media, Greek life, friendships, and dating — and somehow staying deeply self-aware through it. We get real about college dating culture, situationships, exclusivity, and how proximity can blur the line between liking someone and just being attached. Sunny opens up about toxic dynamics, knowing when to walk away,
What Happens When You Actually Try to Change Your Life
This week on Cohosts for Life, Jake and I catch up on a very full week from our 20 week challenge updates to Barkley’s unexpected ER visit, my first real ski trip in years, and why I am now determined to get Jake on the mountain. We also talk content burnout, engagement slumps, and a listener dating follow-up. I'm matching donations this week for Planned Parenthood of Greater NY! htt
What It’s Really Like Being a Single Man at 37
Brandon, from the episode “How to Not Lose Hope That Your Person Is Still Out There,” is back today to share what’s shifted since we last spoke. We talk about dating in your late 30s after divorce, dating app burnout, asking someone out in real life, and the quiet pressure of timelines around marriage and kids. Brandon opens up about holding hope while preparing for different futures, red
Guilt Can Actually Improve Your Relationships
In this episode, I’m joined by Dr. Chris Moore, psychology professor and author of The Power of Guilt, to unpack why guilt shows up so intensely in dating, friendships, and relationships, and why it’s not always a bad thing. We talk about the difference between guilt and shame, why women tend to feel guilt more deeply, how guilt can keep us stuck in dating situations longer than we should
20-Week Challenges, Who Am I Online? & Dating Dilemmas
Jake and I talk through our 20-week challenges, from ambitious reading goals to posting trial reels and what consistency actually looks like in real life. I open up about my ongoing social media identity questions, the pressure to “pick a lane.” Plus, we answer listener questions, including mixed signals after a first date, getting ghosted, deciding if you’re ready for a dog while s
From Situationship to Marriage: What Actually Changed
Blair West joins me to talk about timing, chemistry, and what actually makes a relationship last. We get into slow burns, dating someone who isn’t “ready,” and how to protect your heart without closing it off. Blair shares her real-life love story—from college crush to marriage—and what partnership looks like beyond the honeymoon phase. This one’s about choosing someone who shows up when
When Your First Love Becomes Your Last
In this episode, I’m joined by Liz Woods to talk about love, long-term relationships, and what it’s really like to grow up with your partner instead of dating around. We get into meeting your person young, navigating years of long distance, and how friendships shift when you’re the only one not in the dating trenches. Liz shares what she’s learned watching her single friends date, why bei
The Hard Conversation That’s Making Our Marriage Stronger
On this week's Cohosts For Life ep, we’re sharing a recent conversation about mental load, showing up differently in a relationship, and what it actually means to “step up.” Jake takes the lead on the mic as we talk about unlearning old patterns, sharing the doing, and why small, intentional actions matter more than big promises. We also introduce our new 20-week challenge: one hard thing
45% of Men Have Never Approached a Woman
It’s the first episode of 2026 and we’re starting with a real conversation about dating, happiness, and letting go of the timeline we thought we were on. Stella Stephanopoulos joins me to talk about being single without spiraling, why wanting a relationship isn’t the same as needing one, and what dating actually looks like when you stop chasing validation. We get into red flags, confidenc
The Year I Slowed Down: Career Pressure, Marriage & Burnout (2025 EOY Ep)
In our annual end-of-year episode, Camila Vola turns the mic on me for an honest reflection on a year defined by slowing down. We talk about career pressure, burnout, marathon setbacks, marriage, and the tension between real impact and chasing numbers. I share what I learned about boundaries, growth, and choosing meaning over metrics, plus the dating advice I’d give my single self going i
Recommended
The Sex Addiction Podcast For High-achievers and Entrepreneurs
SMARTnie o Biznesie
A Slob Comes Clean
Rudy Zerbi
إلهَام
10 Bell Pod
The Infinite Inning
Guiding God‘s Girls
The Clinic Marketing Podcast | Local SEO & Healthcare Online Marketing Tips for Clinic Owners & Wellness Providers
Money Magnet Mode | Daily Affirmations That Work,
DJ BURST 305
The No BS Spiritual Book Club with Sandie Sedgbeer
