In this episode of Dating Intentionally, I’m joined by Caroline Winkler, one of my favorite YouTubers with nearly 1M subscribers! Caroline is also the co-host of the Not For Everyone podcast. I reached out to Caroline after seeing her amazing video on relationship with her fiance and how she redefined the age-old advice to "date outside your type." We’re diving into the messy, powerful journey of breaking out of co-dependence and learning how to build real self-trust. Caroline opens up about how she stopped abandoning herself in relationships, started honoring her boundaries, and eventually found someone who could meet her there. We talk emotional availability, the courage it takes to change, and what it really looks like to date intentionally. At the end, we answer a dating dilemma from a woman who doesn't love how her date treats her pet. This one will inspire you! 

Here's the video I'm referring to about Caroline's story about her engagement and dating outside of her type!

Connect with Caroline Winkler 

Check out her podcast here

Slide into her DM's on Instagram

Caroline's Youtube channel

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In this episode, I’m breaking down the difference between healthy pursuit and unhealthy chasing in dating, because yes, there’s a big difference. I share personal stories of times I chased and was chased, plus the subtle signs someone’s just not that into you (and what to do when that’s the case). You’ll learn how to check your own behavior, spot disinterest early, and avoid wasting energy trying to prove your worth. I also answer listener questions about texting, planning, and "being too available," and wrap up with a new segment, Text Support, and a dating dilemma about a fast-burn romance.

My episode on showing interest in someone - 148

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What you wear on a date matters, but not how you might think! In this episode, I’m joined by professional stylist Cassandra Sethi, founder of Next Level Wardrobe, to talk about how to dress with confidence and put together stylish outfits in under a minute. We get into how to create outfits that reflect who you are and what to do if your closet just isn’t working for you anymore. Cassandra shares practical, no-fluff advice on building a wardrobe you actually like, shopping sustainably, and dressing through body changes or life transitions. She also breaks down go-to first date outfit formulas for both women and men, plus tips for looking casual but still put together.

MORE ON CASSANDRA SETHI:

Check out Next Level Wardrobe

Find Your Style Quiz!

Follow Cassandra Sethi on IG

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In this throwback episode, I’m breaking down the difference between sparks, chemistry, and compatibility and why chasing the spark can actually hurt your dating life. We’ll talk about what the spark really is (spoiler: it’s brain chemicals), why it fades fast, and what matters more for a long-term relationship. I share the three biggest myths about sparks, plus tips for building real chemistry and knowing when to keep dating someone, even if you're not feeling butterflies out of the gate. This episode originally aired on 2/13/2024.

MENTIONED IN THIS EPISODE:

* How to Not Die Alone by Logan Ury

* Ep. 27 – How To Tell If Someone Is A Good Match

* My course: How to Identify Your Needs 

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In this bonus episode, I'm sharing my thoughts on the new movie, "Materialists." I'm breaking down what this film says about love, money, capitalism and dating for the long term, and what it got right about today's dating culture. If you haven't seen this movie yet, beware of spoilers! I'd love to hear your thoughts on this too, so drop your hot takes in the comments below.

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In this episode, I’m diving into the magic of the real-life meet-cute (yes, it still happens)! You'll hear voice notes from listeners sharing stories about how they met people off the apps, plus my own reflections on building confidence to strike up conversations wth strangers, flirting in everyday situations, and saying yes to new experiences. At the end, we’ll talk about what adult summer camp taught me about connection and the power of community. I'm also sharing a new segment called Date Idea Drop to inspire you to have dates that aren't just drinks and dinner. 

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Ever fallen for a friend? Struggled to balance dating and maintaining your closest connections? In this episode of Dating Intentionally, I’m joined by friendship expert and journalist Anna Goldfarb, author of Modern Friendship, to talk about the emotional intelligence it takes to navigate friendship, dating, and everything in between. We explore the blurred lines between platonic and romantic relationships, how to communicate when feelings for a friend grow, and why the quality of your friendships directly impacts your success in dating. Whether you’re craving deeper connection, feeling burned by fading friendships, or wondering if not having close friends is a red flag, this conversation is for you. At the end, we get into an email from a listener who feels resentful toward her friends' indifference about world issues. 

MORE ON ANNA GOLDFARB:

⁠See what’s happening on her Instagram⁠

Her book is SO good- take a peek here 

⁠NEW IRL DATING WORKSHOP⁠

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In this episode, I’m breaking down how to talk about the future in dating without putting pressure on the other person. Whether you’re in the early stages or navigating a new relationship, these conversations can feel tricky, but they don’t have to be. I’m sharing mindset shifts that help, scripts for each stage of dating, what actually creates pressure, and practical ways to bring up future plans without scaring someone off. We’ll also get into how to stay grounded in your own vision while respecting their pace. At the end I answer a dating dilemma and introduce a new segment called Text Support! 

NEW IRL DATING WORKSHOP

https://datingintentionally.myflodesk.com/offline-dating

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In this episode, I’m diving into the often messy, misunderstood world of casual dating. If you’ve ever wondered how to approach it without getting emotionally wrecked or unintentionally leading someone on this one’s for you. I’m breaking down how to date casually with clarity, from being upfront about your intentions to setting boundaries that protect your energy. We’ll talk about why emotional detachment matters, how to enjoy casual connections without automatically making it about sex, and what to do if you catch real feelings.

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In this episode, I’m joined by Danny Goldstein, founder of the Austin-based matchmaking company Crux Compatible, to talk all things compatibility, chemistry, and intentional dating. Danny has a fascinating journey, from practicing law to running a matchmaking business rooted in a deep understanding of what actually makes two people a good fit. We dive into his unique process, including the extensive questionnaire he uses with clients, and break down the qualities that truly matter in early dating versus the ones we tend to over-prioritize. Danny shares how to plan dates that reveal real compatibility, what he sees daters get wrong most often, and his personal playbook for making early connections feel both fun and meaningful. If you’ve ever felt unsure how to spot real compatibility, this episode is for you!

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