I'm chatting with my best friend Rachel Saslaw, founder of Storytell NYC. She talks about how she spent six years actively dating before landing a committed relationship with an amazing match in an unexpected way. We're discussing everything from why she refused to subscribe to the "men suck" mentality to using dating as a training ground for self-discovery to the "flirting with life" energy that shifted everything. At the end, we tackle a dating dilemma about a guy who went quiet right before a planned first date, then resurfaced at the last minute with a long explanation.

YOU'LL LEARN...

• Why hating men won't help you date men (same goes for men dating women!)
• How to set a "minimum viable goal" for dating when your calendar is packed
• Why the most aligned version of you is the one who attracts the right person
• How to give a new person a blank slate after you've been burned
• The case for grieving your single years and not racing past them
• Why low-barrier first dates (the coffee walk) beat the high-stakes dinner

MENTIONED IN THIS EPISODE

• The book we'll never shut up about, The Artist's Way
• StoryTell - a live storytelling event in NYC

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In this episode, I'm breaking down the 3 core mistakes that lead people to commit to the wrong person. It's not a broken picker or a shortage of good people out there. I'm covering why dating for potential keeps you stuck, what happens when you don't know or can't communicate your non-negotiable needs, and why ignoring your gut (which is quieter than anxiety) almost always backfires. I share my own stories from past relationships, what these mistakes actually look like in real time, and what to focus on instead, so you can choose someone you don't have to abandon yourself to keep.

MENTIONED IN THIS EPISODE

Download my free dating guides (texting, reflections, FAQ)

Relationship Needs Masterclass

How To Leave Your Situationship

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I'm chatting with Sandy Weiner, a dating coach who has spent 13 years helping people date after divorce, and started her own dating journey at 52 after leaving a 23-year marriage. We're discussing everything from knowing when you're actually ready to date again to navigating the "jaded factor" in midlife dating to having the dating conversation with your kids (at any age). Sandy also shares why being picky about what matters and wide open about what doesn't is the mindset shift most people miss, plus how she creatively meets people offline through meetups, classes, and even emailing her network with her dating profile. At the end, we tackle a dating dilemma from a 51-year-old single mom in a casual situation with a separated 43-year-old, and whether she should walk away or stay.

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Last First Date Radio

Sandy's IG

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Communication is the most important thing in a relationship, but no one tells you what good communication actually looks like in practice. In this episode, I'm getting into relationship check-ins: the structured conversations my husband, Johnny, and I have had about 70 times over three years, and the single biggest reason our day-to-day relationship is virtually tension-free. I'm walking you through the exact questions we use (based on the Gottman State of the Union method, with our own additions), how check-ins have actually changed our relationship over time, when to start doing them, how to bring it up with your partner without making it weird, what to do if things get heated, and the most common mistakes people make. At the end, I tackle a dating dilemma about whether to give a great connection another shot after months apart.

MENTIONED IN THIS EPISODE

• My original episode on check-ins (ep 14)
• The Gottman State Of The Union check-in format
• My post on other check-in formats
• Free dating guides: datingintentionally.com/gift
• My episode with Zach Brittle on repair vs resolve

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I'm chatting with Trevor Hanson, a licensed marriage and family therapist. He and his team at The Art Of Healing help people move from anxious attachment to secure attachment in a structured, results-oriented way. We get into what anxious attachment actually looks like in dating for both men and women, why you can feel totally secure when you're single but completely fall apart once a relationship starts, and what emotionally corrective experiences are, and why they're what actually rewires your nervous system, not just reading more books or gaining more self-awareness. Trevor also shares why you don't need to be fully healed before you date, how conflict, followed by repair, builds real security over time, the problem with using AI to write your texts, and more. At the end, we tackle a dating dilemma from a guy who's not sure how to follow up after sending someone a rose on Hinge.

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Emotional availability is one of the most desired traits in a partner, but it's so hard to find. In this episode, I'm walking through four real listener dilemmas that show how emotional unavailability actually shows up: from being blindsided by a breakup after a seemingly perfect relationship, to oversharing too early with someone you barely know, to getting stuck in a months-long holding pattern, to wondering if your sky-high standards are actually a wall. I'm breaking down what emotional availability really looks like, why "chasing the feeling" keeps people stuck, and how to start recognizing emotional availability so you don't miss it.

MENTIONED IN THIS EPISODE

• Episode 152 - a deeper dive on emotional unavailability
• Episode 217 - with Julia Kristina, a therapist and expert on emotional intelligence and maturity
• Episode 255 - healing anxious attachment with Rebecca Ore

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This episode originally aired on Sex Ed with DB!

In Sleepless in Seattle, a woman hears a stranger’s voice on the radio and decides she has to be with him. A few cross-country flights, some light stalking, and one dramatic Empire State Building finale later. Was it a recipe for true love? Or just another rom-com ignoring boundaries in the name of "destiny?"

In this episode, I joined DB to unpack the film’s gender dynamics, its borderline obsessive premise, and why rom-coms always overlook the stable, reliable guy.

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I'm chatting with Hanna Anderson and Mackenzie Foltz, the co-hosts of The Dating Detectives, a podcast that combines real PI work with deeply ethical storytelling about people who got conned in love. We're discussing everything from what "dogfishing" actually is (and how it's different from catfishing) to the subtle early red flags most people miss, to why love bombing feels so good even when it's a setup. Mackenzie and Hanna also share their PI-approved guide to vetting someone you're dating without feeling "crazy," including the exact line to use when you've found something on them, plus practical safety tools every single person should know about. At the end, we tackle a dating dilemma about a guy who keeps liking other women's photos on Instagram after being asked to stop.

MENTIONED IN THIS EPISODE

"The Origin Story" — the case that inspired the show

The crypto catfish (FaceTime sob story episode)

The "time-traveling" investor episode

The Twitter vegan episode

The "evil stepmother" episode

My guest appearance on The Dating Detectives!

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CONNECT WITH ME:

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MORE FREE ADVICE & CONTENT

Download my free dating guides (texting, reflections, FAQ)

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See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.