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Two best friends sitting down with different therapists and experts every week to talk through the stuff everyone struggles with but nobody says out loud. Anxiety. Dating. Relationships. Career. Family Dynamics. Grief. The list goes on. We're not experts. We're just two very curious, slightly unhinged guys who can label our feelings (most of the time). Because therapy’s expensive, but thankfully podcasts aren’t ;) Subscribe and follow along on IG at @freetherapy and TT at @freetherapypod
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This week is our first ever Therapy in Session, where guys sent us anonymous messages about what they’re struggling with and a therapist answered them. Seth Menachem is back, a therapist here in LA who runs the Menachem Psychotherapy Group. The questions covered getting back with an ex, starting over in a new career, losing yourself the second you start dating, and who should be paying on dates. Across all five, it became clear that when it comes down to it, we’re all going through a lot of the same struggles, and nobody is as alone in them as they think. Got something you’re struggling with? Send us an anonymous voice note at freetherapypod.com/questions and you might hear it answered on the next Therapy in Session. New episodes every week. Follow on the iHeart app, Apple Podcasts, Spotify, or wherever you get your podcasts and on Instagram at @freetherapy. And as a reminder, we are not therapists, and while this may feel like therapy, it’s not. So if you’re struggling, please reach out to a mental health professional who can help. 00:00:00 – Intro 00:02:04 – In Bed With an Ex 00:09:25 – Scared to Start Over 00:19:34 – Losing Yourself When Dating 00:24:12 – Who Pays on Dates 00:37:05 – Being More Present 00:42:04 – Career Uncertainty See omnystudio.com/listener for privacy information.
Kristan Sargeant joins us to explore shadow work, the parts of ourselves we’ve learned to hide, and how they can keep us from going after what we want. You want to speak up, set a boundary, ask someone out or take a chance on something you care about. But then you imagine how it could go wrong, and talk yourself out of it. A coach who studied under Phil Stutz, Kristan explains how she works with the shame and fear of rejection underneath those moments. We get into why understanding your patterns doesn’t automatically change them, how needing everyone’s approval can quietly run your life, and what it means to stay on your own side even when things don’t go your way. She also shares practical exercises for getting to know your shadow and comparing what you’re afraid will happen with what actually happens when you take a risk. If you’ve ever known what you wanted to do and still couldn’t bring yourself to do it, this one is for you. 00:00 intro to shadow work tools 03:41 shadow work starts with self-acceptance 10:08 hidden shame can drive behavior 20:08 your triggers reveal your shadow 26:29 others’ expectations can shape your life 36:37 shadow work supports taking risks See omnystudio.com/listener for privacy information.
This week is about what men really need to open up in a relationship, and why asking him to talk about his feelings might be the thing that makes him shut down. Kristina Ferrari is a licensed professional counselor with a master’s in mental health counseling, and she’s been in therapy herself for over 15 years. She makes the case that modern therapy is failing men because it’s built around a style that favors talking things through, while most guys show up wanting to solve something and move forward. As a therapist who does a lot of relationship work, she also challenges the idea that women are better at relationships, including how women communicate when they’re upset. Then she walks us through her REAL framework for working with men: Respect, Expertise, Action, and Leadership. It’s a roadmap for understanding what helps a man feel safe enough to get to the deeper stuff. If you’ve ever said “just tell me what’s going on” and gotten nothing back, this one is for you. New episodes every week. Follow on the iHeart app, Apple Podcasts, Spotify, or wherever you get your podcasts and on Instagram at @freetherapy. And as a reminder, we are not therapists, and while this may feel like therapy, it’s not. So if you’re struggling, please reach out to a mental health professional who can help. 00:00:00 – Intro 00:01:42 – Why Therapy Is Failing Men 00:05:03 – Coaching vs. Therapy 00:17:18 – Women Aren’t Better at Relationships 00:22:41 – The REAL Framework See omnystudio.com/listener for privacy information.
This week is about the journey to healing, not the moment you lose someone, but everything it actually takes to rebuild after. Our guest is Zak Williams, mental health advocate, founder of the wellness brand Pym, and the son of Robin Williams. He's been in therapy since he was a small child, and that lifelong relationship with it is part of what's made him such a vocal advocate for men actually getting help. He talks about what actually helped him heal in the years after his father's death, and makes the case that recovery isn't one big breakthrough so much as a set of small, practical shifts - how you think, how you rest, how you show up for other people. It's less about getting over loss and more about building a life that can hold it. He also opens up about the kind of man his father was off-screen, the kindness and generosity that defined him, and by the end, we talk him into blind-ranking his dad's ten most iconic movies, from Good Morning, Vietnam to Mrs. Doubtfire. If you've ever lost someone and felt like you were supposed to have moved on by now, this one is for you. New episodes every week. Follow on the iHeart app, Apple Podcasts, Spotify, or wherever you get your podcasts and on Instagram at @freetherapy. And as a reminder, we are not therapists, and while this may feel like therapy, it's not. So if you're struggling, please reach out to a mental health professional who can help. 00:00:00 – Intro 00:06:44 – Why Men Misunderstand Therapy 00:12:14 – Training Your Brain Like a Muscle 00:17:33 – Grief, Service, and Healing 00:23:10 – Ranking Robin Williams' Movies 00:28:02 – Building Pym After Loss See omnystudio.com/listener for privacy information.
This week we explore psychedelic therapy with Dr. Nick Brüss, whether it can help you heal, what people misunderstand about it, and why the experience itself is only part of the work. Dr. Nick Bruss is a therapist and researcher who has spent over a decade working in psychedelic-assisted therapy and Internal Family Systems (parts work). We talk about its potential to help people struggling with depression and PTSD, why understanding your past doesn’t always mean you feel better, and what it means to build a different relationship with your emotions. Nick helps us explore what healing requires, and how some of these lessons apply even if you never take psychedelics. If you understand why you’re struggling but still feel stuck, this one might be for you. New episodes every week. Follow on the iHeart app, Apple Podcasts, Spotify, or wherever you get your podcasts and on Instagram at @freetherapy. And as a reminder, we are not therapists, and while this may feel like therapy, it's not. So if you're struggling, please reach out to a mental health professional who can help. 00:00 Intro 05:04 Psychedelic Therapy: Benefits and Risks 08:41 Ketamine, MDMA, Psilocybin, and the Research 15:19 Feeling Stuck and Parts Work 25:36 Getting Better at Feeling 28:41 Integration and Healing Beyond the Session See omnystudio.com/listener for privacy information.
This week is about OCD, what it actually is, why it's so widely misunderstood, and how it can look nothing like what you'd expect. Allegra Kastens is a licensed therapist here in LA who specializes in OCD, and this is the most in-depth conversation we've had on the topic. She breaks down the real difference between an intrusive thought and a compulsion, and makes the case that fighting or suppressing the thought is what actually keeps OCD in control. It's a far more common condition than people realize, and one of the least visible. If you've ever been scared by your own thoughts, or you love someone whose mind won't let something go, this one is for you. New episodes every week. Follow on the iHeart app, Apple Podcasts, Spotify, or wherever you get your podcasts and on Instagram at @freetherapy. And as a reminder, we are not therapists, and while this may feel like therapy, it's not. So if you're struggling, please reach out to a mental health professional who can help. 00:00:00 – Intro 00:09:00 – What OCD Actually Is 00:15:10 – Taboo Obsessions and Why They're So Common 00:31:29 – OCD vs. OCPD 00:44:08 – Shame, Men, and Staying Silent 00:48:50 – Relationship OCD 00:54:17 – Getting Help See omnystudio.com/listener for privacy information.
This week, we sit down with New York Times bestselling author and clinical psychologist Dr. Shefali to talk about why men feel so misunderstood and what we’re getting wrong about masculinity. We explore the pressures men face, how the way we raise boys shapes their relationships, and what it takes for men and women to better understand each other. It’s an honest, hopeful conversation about moving beyond blame, making room for strength and vulnerability, and raising a more emotionally connected generation. If you’ve ever struggled to understand yourself or the men in your life, this one is for you. New episodes every week. Follow on the iHeart app, Apple Podcasts, Spotify, or wherever you get your podcasts and on Instagram at @freetherapy. And as a reminder, we are not therapists, and while this may feel like therapy, it's not. So if you're struggling, please reach out to a mental health professional 00:00 Intro 05:44 Conscious Masculinity 17:34 Shame and Male Role Models 28:31 Strength and Vulnerability 36:47 Disconnection and Connection 47:11 Raising Conscious Boys See omnystudio.com/listener for privacy information.
This week is about what actually makes a man attractive today, why vulnerability is the real glue in any relationship, and how to stop taking your partner's feedback as criticism. Aliza Shapiro is the therapist behind @therapist_in_nyc, and she has an incredible read on how relationships actually work right now. She breaks down the three traits women consistently find magnetic, and makes the case that holding it together isn't strength, opening up is. If you've ever held something back from your partner because you thought it would make you look weak, this one is for you. New episodes every week. Follow on the iHeart app, Apple Podcasts, Spotify, or wherever you get your podcasts and on Instagram at @freetherapy. And as a reminder, we are not therapists, and while this may feel like therapy, it's not. So if you're struggling, please reach out to a mental health professional who can help. 0:00 Intro 05:28 Attraction goes beyond financial success 15:30 Feedback can feel like criticism 25:57 Expressing needs without assigning blame 36:06 Feeling heard without fixing everything 43:40 Opening up and repairing connection See omnystudio.com/listener for privacy information.
This week is about inner-child work, the patterns we carry from childhood, and how our past can continue to shape the way we think, feel, and behave as adults. Our guest is Kati Morton, a licensed therapist, author, and educator who has millions of followers online. She joins us to break down what inner-child work actually means, why certain patterns can be so difficult to change, and how understanding where they came from can help us respond differently in the present. We get into how our childhood experiences create an emotional blueprint for relationships, conflict, asking for help, and even how we see ourselves. Kati explains why we can know intellectually that a behavior isn't serving us and still find ourselves repeating it—and what we can actually do about it. We also talk about emotional triggers, boundaries, people-pleasing, and the difference between understanding your past and using it as an excuse. If you've ever wondered why you react the way you do, why you keep repeating the same patterns, or how much of your adult life is still being shaped by your childhood, this episode is for you. New episodes every Thursday. Follow on the iHeart app, Apple Podcasts, Spotify, or wherever you get your podcasts and on Instagram at @freetherapy. And as a reminder, we are not therapists, and while this may feel like therapy, it's not. So if you're struggling, please reach out to a mental health professional who can help. See omnystudio.com/listener for privacy information.
For this special bonus episode, Ben shares his experience volunteering at Experience Camps, a free nonprofit camp for kids ages 9–18 who have lost someone they love. After spending a week alongside these kids, Ben talks with Kevin about what he learned about grief, healing, connection, and finding joy even in the middle of loss. To learn more visit www.experiencecamps.com See omnystudio.com/listener for privacy information.
This week is about relationships, how to know if someone is actually right for you, and whether you're being too picky or holding out for what you really want. Our guest is Beverly Teller, Ben's mom, a longtime therapist, and one of the most requested guests we've had on the show. She's also been giving Kevin “free therapy” around the dinner table for years. We get into what makes a relationship right for you, what you should and shouldn't compromise on, and how to tell the difference between having standards and protecting yourself from getting hurt. Kevin opens up about what he was looking for in a partner, the pressure he put on himself to become “good enough,” and what dating taught him about himself. We also talk about healthy conflict, why relationships don't need to be free of disagreement, and how to know when you're fighting to be right instead of trying to understand each other. If you've ever wondered whether you're settling, asking for too much, or just afraid to take the risk, this episode is for you. New episodes every Thursday. Follow on the iHeart app, Apple Podcasts, Spotify, or wherever you get your podcasts and on Instagram at @freetherapy. And as a reminder, we are not therapists, and while this may feel like therapy, it's not. So if you're struggling, please reach out to a mental health professional who can help. 0:00 Intro to Ben's mom 10:30 Are you in the right relationship? 17:32 Am I being too picky? 23:02 What should I look for in a partner? 32:15 What is holding Kevin back? 44:56 Secret to a lasting marriage 45:30 Why commitment can feel scary See omnystudio.com/listener for privacy information.
This week is about what happens when you finally stop trying to be okay with what happened to you. Ben sits down with his former therapist, Jessica Serber, who helped him work through years of grief and anger after surviving cancer three times before the age of 24. For a long time, Ben thought healing meant moving on, staying positive, and building a life that had nothing to do with cancer. What he eventually learned was almost the opposite: he couldn’t move through the pain until he let himself actually feel it. They talk about the anger Ben didn’t think he was allowed to have, the parts of his life he felt cancer had taken from him, and how finally telling the truth about those feelings changed his relationship with the experience. They also get into what healing actually looks like when the thing that happened to you never completely goes away, and how to show up for someone you love when there’s nothing you can say to make things better. We’ve been best friends since college. We lived in the same house while Ben was going through chemotherapy and still barely talked about what was actually happening. Years later, sitting down with Jess brought us back to conversations we didn’t know how to have then. If you’ve been carrying pain, anger, grief, or something you’ve convinced yourself you should be “over” by now, this episode is for you. You can’t heal what you won’t let yourself feel. New episodes every Thursday. Follow on the iHeart app, Apple Podcasts, Spotify, or wherever you get your podcasts, and on Instagram at @freetherapy. And as a reminder, we are not therapists, and while this may feel like therapy, it’s not. If you’re struggling, please reach out to a mental health professional who can help. 0:00 Reuniting with his old therapist 10:00 Allowed to feel his anger 17:51 Seeing his cancer as trophies 28:09 What to say when someone's struggling 35:28 Getting uncomfortable to heal 42:24 Grief camp and giving back See omnystudio.com/listener for privacy information.
This week, Sandra Kushnir is talking about values, why living out of sync with them quietly chips away at your self-esteem, and how to figure out what yours even are. Our guest is Sandra Kushnir, LMFT, a therapist and the founder of Meridian Counseling, and she gets into where values actually come from, why they matter so much for your mental health, and how to find yours underneath all the noise telling you what you 'should' want. We have both spent way too long measuring our worth against people online and against a version of success we never really chose. Recording this sent us back to values work we had done years ago and mostly forgotten, and it turned out we had drifted further from ours than we wanted to admit. If you have everything you were told to want, and still feel a little off, this one is for you. New episodes every Thursday. Follow on the iHeart app, Apple Podcasts, Spotify, or wherever you get your podcasts and on Instagram at @freetherapy. And as a reminder, we are not therapists, and while this may feel like therapy, it's not. So if you're struggling, please reach out to a mental health professional who can help. See omnystudio.com/listener for privacy information.
This week's episode is about sex, women's biggest complaints about men in the bedroom and what men get wrong about sex. Rachel Overvoll is a sex expert trained at the Kinsey Institute, and this was on of our most fun episodes we've recorded yet. We get into the biggest turn-offs women won't say to your face, what pleasure means for two people, and why guys have it all wrong in the bedroom. She makes the case that the best sex happens when both people are being a little selfish, and completely dismantles the myths most men have been carrying since they were teenagers. If you've ever wondered whether you're actually good in bed, or you just want to be better for your partner, this one's for you. New episodes every week. Follow on the iHeart app, Apple Podcasts, Spotify, or wherever you get your podcasts and on Instagram at @freetherapy. And as a reminder, we are not therapists, and while this may feel like therapy, it's not. So if you're struggling, please reach out to a mental health professional who can help. 00:00:00 – Intro 00:03:34 – Every Guy Experiences The Same Thing 00:12:28 – Mandatory Book To Read For Men 00:19:42 – Women's Biggest Complaints in The Bedroom 00:28:29 – Penis Size Myth 00:32:31 – What Women Wish Men Knew About Sex 43:08 -- Conversation About Porn See omnystudio.com/listener for privacy information.
This week's episode is about male friendships, why it's so hard for guys to make real friends as adults, and why men opening up to each other is so tough. Our guest is Seth Menachem, a therapist here in LA who runs the Menachem Psychotherapy Group. By the time we were done, we felt like we had made a new best friend. We went deep into into why so many men are lonelier than ever and one small move that can shift an entire friend group. If you've got buddies, but no one you can call at 2am, or are looking to go deeper in your friend circle, this one's for you. New episodes every week. Follow on the iHeart app, Apple Podcasts, Spotify, or wherever you get your podcasts and on Instagram at @freetherapy. And as a reminder, we are not therapists, and while this may feel like therapy, it's not. So if you're struggling, please reach out to a mental health professional who can help. 00:00:00 – Intro 00:02:31 – Why Men Struggle To Be Vulnerable 00:11:28 – The Secret To Making Friends 00:16:26 – What To Do When Your Triggered 00:26:30 – Why Curiosity Is Important 36:30 -- Why Opening Up Is Tougher Than Staying Silent See omnystudio.com/listener for privacy information.
When times are hard, we look for wisdom to get us through those moments. Whether it's an author, a poet, or a world leader, there are lifetimes of experience we can look back on to find a little solace. This week, no therapist, just Ben & Kevin sitting down to share the wisdom that feels like therapy to them. The quotes, the mantras, and the lines they come back to when everything feels like too much. They shared lines from Steve Jobs, Ram Dass, Brene Brown, Seneca, Yung Pueblo & others as well. If you've ever needed something to hold onto when things get hard, this one's for you. New episodes every week. Follow on the iHeart app, Apple Podcasts, Spotify, or wherever you get your podcasts and on Instagram at @freetherapy. And as a reminder, we are not therapists, and while this may feel like therapy, it's not. So if you're struggling, please reach out to a mental health professional who can help. 00:00:00 – Intro 00:06:29 – How to Dance Through Life 00:09:00 – Trusting That It Will Work Out 00:13:00 – Everyone Wants To Be Loved 00:22:30 – What is authenticity 00:29:20 – Sayings Ben Thinks Are Bullshit See omnystudio.com/listener for privacy information.
This week is about anxiety and rumination, and why trying to get rid of your anxiety is exactly what keeps it going. Kimberley Quinlan is an amazing therapist who specializes in anxiety and rumination. In this episode she gets into why a thought is not a fact, why avoidance quietly shrinks your entire life, and what she actually does at 3am when her brain won't turn off. It is not what you'd expect!! We found out during this episode that we've been feeding our anxiety for years without realizing it. She pointed out all the little ways we treat anxious thoughts like they're important, and why attention control is the key to retraining your brain out of the spiral. If you're the one lying awake at 2am running the same loop, this one is for you. New episodes every week. Follow on the iHeart app, Apple Podcasts, Spotify, or wherever you get your podcasts and on Instagram at @freetherapy. And as a reminder, we are not therapists, and while this may feel like therapy, it's not. So if you're struggling, please reach out to a mental health professional who can help. 00:00:00 – Intro 00:02:24 – Why You Can't Get Rid of Anxiety 00:09:32 – A Thought Is Not a Fact 00:15:10 – Why We Ruminate 00:22:12 – Avoidance and Doing It Scared 00:24:55 – The 2AM Spiral See omnystudio.com/listener for privacy information.
Our guest this week is my former therapist, Koorosh Rassekh! We talk about where people-pleasing actually comes from, why it isn't a flaw you need to fix but something that once kept you safe, and the techniques that actually make hard conversations easier. For most of my life I thought keeping the peace made me a better friend, partner, and person. I'd suppress my needs, avoid the conversations I was dreading, and tell myself I was just being easygoing. But it actually just built quiet resentment and slowly ruined my relationships. If you say yes when you mean no, or you've been sitting on a conversation for months because you're afraid of how it'll land, this one's for you. – Kevin New episodes every week. Follow on the iHeart app, Apple Podcasts, Spotify, or wherever you get your podcasts and on Instagram at @freetherapy. And as a reminder, we are not therapists, and while this may feel like therapy, it’s not. So if you’re struggling, please reach out to a mental health professional who can help. 0:00 Intro: people-pleasing and conflict avoidance 6:59 Why you're not broken 9:47 Why expressing needs feels impossible 13:16 People-pleasing caught in real time 24:58 How to have hard conversations 41:08 Signs you're people-pleasing, and the cost See omnystudio.com/listener for privacy information.
This week is about attachment styles and how to rewrite the one you grew up with. Someone takes three hours to text back and you start spiraling. Or things finally start to get good and you start pulling away for absolutely no reason. It isn't random and it isn't a character flaw. It's your attachment style, and most of us were never taught we had one. Today, we sit down with German psychologist Jenny Meinen, who studied attachment theory. We get into where these patterns come from, why anxious and avoidant people keep finding each other, and why the work underneath all of it is self-worth. Jenny breaks down what a secure conversation actually sounds like out loud, why the repair after a fight matters more than the fight, and the line Kevin is still trying to live by: their mood is not a threat to me, and I'm not responsible for other people's emotions. If you've ever needed reassurance you were too embarrassed to ask for, or gone cold the second things got real, this one's for you. You'll probably know your style before the guest even shows up. Also, a reminder that we are not therapists, and if you are really struggling, to get the support you need <3 See omnystudio.com/listener for privacy information.
Someone you love is grieving and you have no idea what to say. So you say nothing, and that's the one thing you shouldn't do. Grief therapist and author Claire Bidwell Smith has sat with thousands of people through loss and written five books on grief. With Father's Day approaching, Ben opens up about losing his dad Mickey three years ago. Claire breaks down how to actually show up for someone who's grieving, why anxiety after loss is something nobody talks about, and how conscious grieving can give you the tools to heal. If you've ever lost someone you love, or you love someone who has, we think Claire can help. New episodes every week. Follow on the iHeart app, Apple Podcasts, Spotify, or wherever you get your podcasts and on Instagram at @freetherapy. See omnystudio.com/listener for privacy information.
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Observed November 4, 2026.
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