Positive & practical advice to help you love your dating life (and the rest of life, too)
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About The Show
On Finding Mr. Height: The Podcast, dating & relationship coach Ali Jackson brings you her positive and practical approach built from personal experience in the dating trenches. No matter where you are in your relationship journey, you’ll learn how to identify your needs, embrace your feelings, and directly communicate both.
Ready to feel more authentic and grounded in your relationships and more joyful in your life overall? Tune in as Ali brings you relatable conversations with both expert guests and listeners just like you, peppering in her own personal insights along the way
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Meet your Host
Ali Jackson is a dating coach with a positive mindset who’s been there, in the trenches, looking for her person in New York City. She’s taken her experience and turned it into personalized programming designed to help you refine what you’re looking for…and then go get it. Now, she brings that expertise to the world of podcasts. Learn More or follow her on TikTok & Instagram.
episodes
Going through a breakup? Anxious thoughts feeling overwhelming? Struggling with dating app burnout? Hit Ctrl+F (or Command+F) to search for the perfect episode.
Episode #280 - Live a Longer Lonely Life: What Tech Is Actually Doing to Connection ft. Alex Wolf
Alex Wolf, the founder behind the original Boss Babe movement turned tech philosopher, joins Ali to explore what the attention economy is quietly doing to our ability to connect with each other, including romantically. The conversation covers why “just delete the app” misses the point entirely, why the speed of technology adoption is the real problem, and how dating apps have the same design problem as social media: they weren’t built to facilitate actual connection. The two also chat about dead internet theory, what cobras have to do with your match count, and why it seems increasingly impossible to go back to anything analogue.
Episode #279 - Hot Topics #23: First-Time Manager Nerves, Single Mom Dating Apps, Timeline Anxiety, Dating Burnout, and the Talking Stage
Ali answers five listener questions that all share a common thread: the gap between wanting something and being able to follow through. A first-time manager grappling with imposter syndrome, a single mom navigating kid disclosure on the apps, someone processing timeline anxiety after leaving a relationship, a dater hitting a wall with the performance exhaustion of first dates, and someone three weeks deep in a texting situation who can’t figure out how to suggest meeting up.
Episode #278 - Listener Storytime: Rebuilding Intimacy After Desire Faded
This week, Ali is joined by Sarah, a listener who reached out to share her journey with desire and intimacy. Sarah opens up about how her health anxiety quietly muted her desire for sex until she sought out a specialized sex therapist, and how that work helped her reframe arousal, communicate with her husband, and rebuild a sex life that works for both of them. They also touch on practical tools that helped Sarah in her work, including the book “Women on Top” by Nancy Friday and try the Unbound Intimacy Deck for cards like Sarah describes.
Episode #277 - What If the Best Dating Profile Was Written by Your Best Friend? ft. Brooke Janousek
TW: This episode contains a brief discussion of cancer and loss. If you want to skip it, the guest segment begins at approximately minute 13.
Brooke Janousek, founder of Someone You Should Meet, joins Ali to make the case for letting the people who know you best do the talking. Brooke and Ali dig into why apps fail to capture who people actually are, the courage gap between professional and personal life, and what inspired Brooke to start hosting in-person dating events (hint: it was attending a lackluster one herself). The two also chat about what it’s like to finally walk away from a situationship that isn’t working, and how that comes back to the frustrations of dating overall.
Episode #276 - Ali’s Guide To Getting The *Right* Job Offer (Parts 1 & 2 of 3)
You’re being interviewed, but you’re also doing the interviewing. Most people forget the second part. Ali shares two episodes from the Finding Mr. Height Patreon in this special re-air, covering the interview process from both sides of the table. Part one is a practical guide to vetting a company before you accept an offer: how to use Glassdoor beyond the surface level, what LinkedIn can tell you about turnover patterns, how to interview your interviewer, and more. Part two covers your side of the table: how to tell a coherent, compelling story about your career, how to answer questions with real specificity instead of canned talking points, and why the questions you ask can say just as much about you as the answers you give.
Episode #275 - When You Outgrow the Life You Built ft. Sarah Vacchiano
This week, Ali sits down with Sarah Vacchiano, author of Soft Launch, who got married at 21, divorced at 27, and moved to New York City to start over from scratch. Sarah shares what it felt like to leave a marriage that looked fine on the outside, how she navigated a world she’d skipped the entry points to, and what it took to finally build an identity that was genuinely hers. She remarried at 37, and the conversation gets into what was fundamentally different about love on the other side of all that work.
Episode #274 - Listener Storytime: When Staying Felt Safer Than Leaving
TW: This episode includes discussion of grief, miscarriage and emotional abuse.
This week, Ali is joined by a listener who shares her story of leaving a marriage rooted in cultural pressure, low self-worth, and years of emotional abuse. The conversation covers the internal voice she ignored while engaged, the compounding grief that finally pushed her out the door, and what it’s looked like to rebuild on the other side.
Episode #273 - Two Years In: The Anniversary Episode ft. Skyline
Ali and Skyline are celebrating two years together! Together from Italy, they go deep on what two years actually looks like, covering how they handle disagreements, how intentional they’ve been about the relationship and whether that was by design or just who they are, what they’ve each learned about themselves through the relationship, and what surprised them most about each other along the way. Plus, listeners ask about their couple identity, the little habits that make each other smile, where things are headed next, and which annoying habits irk each other the most. But first, the two recap highlights and a few hiccups from their trip to Italy, sadly coming to an end!
Episode #272 - Designing a Life That Fits ft. Danielle McGeough
Danielle McGeough joins Ali to talk about what happens after you hit the goal you’ve been chasing your whole career and realize it doesn’t feel the way you thought it would (and how this relates to dating!). Danielle, a professor and creator of the RISE Ritual Method, unpacks the difference between burnout and demoralization, why habits alone won’t get you out of a hollow season, and how to design rituals that actually move you from where you are to where you want to be.
Episode #271 - Dating Burnout and the Patterns Behind It ft. Jordanne Sculler
Jordanne Sculler, licensed therapist, joins Ali to talk about dating burnout from the inside out. Rather than pointing to apps or circumstances as the culprit, Jordanne breaks down the internal patterns that are really driving exhaustion in dating, including the productivity trap of treating dating like a to-do list, people-pleasing and self-abandonment, and what it actually looks like to break a cycle that isn’t working. The conversation gets practical with Jordanne’s “do something different” framework, and Ali shares her own experience recognizing these patterns in both dating and long-term relationships.
Episode #270 - The Relationship Advice You Inherited Might Be Wrong ft. Monica Tanner
Marriage coach Monica Tanner joins Ali to challenge the unwritten rulebook most of us absorbed about relationships without ever questioning it. Monica, the author of Bad Marriage Advice, breaks down why a lot of the advice well-meaning people pass down is not just unhelpful but actively working against us. The conversation covers why “never go to bed angry” is a recipe for sleep deprivation, what it actually means to teach your partner how to treat you, and why compromise is not always the goal. Ali also shares her own examples from her relationship with Skyline.
Episode #269 - Interdependence, Earned Security, and the Art of Being Unsingle ft. Amy Chan
Amy Chan returns to the pod for an in-person recording with Ali, a conversation spurned from her own deep attachment work. The two chat about Amy’s new book Unsingle, where she leverages her personal experiences to help you identify your recurring patterns in relationships. The two get into why you keep choosing the same person in a different body (and how to actually change that), the mechanics of dating from first swipe to long-term commitment, and what healthy interdependence looks like.
Episode #268 - Listener Storytime: Building a Full Sex Life on Your Own Terms
This week, Ali sits down with Julia, a listener who shares her experience discovering that vaginal sex just doesn’t work for her body. She walks through how that shaped her early dating experiences, including a two-and-a-half year situationship, and what it was like to tell her current partner. They get into why penetration isn’t the gold standard of sex, how societal expectations create feelings of unworthiness, and what it looks like to build a full and satisfying sex life on your own terms.
Episode #267 - The Deeper Pattern Beneath Your Dating Life ft. Meg Tuohey
Relationship coach and author Meg Tuohey joins Ali to introduce her concept of the HeartPrint, the idea that each of us is as unique as our fingerprints in how we move through the world and relate to others. Meg breaks down why frameworks like attachment styles and love languages, while helpful, can only take us so far, and how real self-knowledge requires a deeper, more individualized kind of attunement. The conversation covers why we’re drawn to familiar patterns in dating even when they don’t serve us, what it actually looks like to move from awareness to change, and how the walls we’ve built to protect ourselves can be honored without letting them define our future.
Episode #266 - The NYT Tried to Give Us Dating Rules and We Have Notes ft. Darcy
Returning guest and Ali’s good friend Darcy is back on the pod, and they’re diving straight into the New York Times’ crowdsourced list of 35 dating rules. Some of them? Genuinely solid. Some of them? Completely unhinged. And several of them directly contradict each other, which is so indicative of modern dating. Topics include how people treat servers, outsourcing your nervous system to a partner, paying on dates, the pacing of physical intimacy, whether you actually need to like someone’s friends, and a $75 first-date filet mignon story.
Episode #265 - Dating Advice We Wish We'd Taken Sooner ft. Ilana Dunn
Ali sits down with Ilana Dunn, host of Seeing Other People, for a conversation about the dating advice they both either ignored in the past or wish they’d taken sooner. They dig into the patterns that kept them stuck longer than necessary: from ignoring gut feelings and making excuses for bad behavior, to chasing potential over reality and performing chill they never actually felt. Listener submissions are woven throughout, and the conversation gets personal fast: secret relationships, toxic situationships, unreliable narrators, and the moment things finally felt different with the right person.
Episode #264 - Hot Topics #22: First Messages, Being Someone's "Type," and People-Pleasing in Progress
We’ve got some amazing listener questions this week, and the thread running through all of them is a concept introduced in this week’s Media Mention: high involvement, low attachment, inspired by a TikTok from @mother.of.a.dilemma.
Episode #263 - Listener Storytime: Holding Grief While Choosing What’s Next
TW: This episode includes discussion of grief, loss, and suicide. If you or someone you know is struggling, please reach out. You can call or text 988 to connect with the Suicide and Crisis Lifeline — they’re available 24 hours a day, 7 days a week, and it’s free and confidential.
This week, Ali is joined by a listener who opens up about grieving the loss of a partner and navigating life (and dating) while healing from deep trauma. She shares what helped her through the hardest years, how healing unfolded in non-linear ways, and what it’s been like to build a full life on the other side of grief. They explore what it really means to seek connection while carrying grief, the tension between moving forward and honoring loss, and how dating can feel especially complicated after partner loss.
Episode #262 - Are We Watching Love (Is Blind) Stories or Unresolved Patterns? ft. Jackie Dorman
Matchmaker Jackie Dorman joins Ali to break down the latest season of Love Is Blind through the lens of someone who has helped over 1,600 people get engaged or married. They dig into why the pod format rewards anxious attachment, what emotional over-functioning really looks like on screen, and how to tell the difference between genuine chemistry and chaos. Plus, couple-by-couple predictions on who actually makes it to the altar!
Episode #261 -How to Stop People-Pleasing Without Becoming Rigid ft. Dr. Paula Freedman-Diamond
Dr. Paula Freedman-Diamond joins Ali to discuss people-pleasing and how it relates to control in dating and relationships. Paula, a therapist and author of Toxic Striving, breaks down how people-pleasing and rigid boundary-setting are two sides of the same coin: both are attempts to control outcomes and avoid uncomfortable feelings. The conversation explores how to identify when you’re prioritizing external validation over your own values and what the middle ground looks like between being overly accommodating and overly rigid. Paula also shares insights on acceptance and commitment therapy, learning to hold your desires lightly while staying grounded in your values.
Episode #260 - Hot Topics #21: Attachment Patterns, Workplace Feedback, and Dating Dynamics
Ali is back with another Hot Topics episode, starting with listener updates and reflections sparked by a recent listener storytime and a past Hot Topics question. She then dives into your submitted questions, covering losing interest once the chase ends, making sense of mixed signals when someone’s words and actions don’t align, receiving vague “executive presence” feedback at work, and navigating early dating when planning and consistency feel off.
Episode #259 - Using Conflict to Build Trust ft. Anna Lecat
This week, Ali hosts Anna Lecat for a conversation that reframes conflict as a powerful tool for connection rather than something to avoid. Together, the two unpack why so many of us fear uncomfortable conversations (especially in dating) and how that fear can quietly sabotage intimacy.
Episode #258 - Relatability Creates Chemistry: Feel a Real Connection on Dates ft. April Beyer
This week, Ali sits down with veteran matchmaker April Beyer (who has 25+ years in the industry!) to unpack why dating feels harder than ever and how to make it more human again. They talk about letting go of attachment to outcomes, loosening rigid “criteria,” and why going on more dates can actually lead to love faster than waiting for the perfect match.
Episode #257 - Listener Storytime: Designing a Relationship That Breaks All the Rules
Ali sits down with FMH listener Allison for a storytime episode all about building a relationship that works for you, even if it breaks societal norms. Allison shares what it was like feeling like a late bloomer as she navigated finding her now-partner in her late 30’s. From dating a divorced dad with two kids to navigating mismatched timelines around moving in, engagement, and merging lives, Allison walks through how they used curiosity, therapy, and a lot of real conversations to get on the same page without defaulting to what relationships are “supposed” to look like.
Episode #256 - How To Make First Dates More Fun ft. Miriam Katz
Did you ever think that improv could apply to dating? Repeat guest Miriam Katz is back this week, a fun, hands-on conversation about how to feel lighter, more confident, and more authentic on dates…using improv! They talk about tone and enthusiasm, how to practice presence in low-pressure everyday moments, and why “being good” is not the goal if you’re trying to connect like a real human. Ali flips the usual script and lets Miriam run a few playful prompts to demonstrate how loosening up and staying curious can pull you out of performance mode and into actual connection – especially when nerves start to spike. This interactive episode features tools you can use before dates, interviews, and any situation that triggers self-consciousness. And ps: FMH The Pod is now on Youtube so you can see these exercises in action!
Episode #255 - New Year Reset: Foundation, Routines, and Intentional Living
In this New Year episode, Ali shares her word for the year, foundation, and the theme guiding how she’s setting up the year ahead: less chaos, more intention.