In this episode, I’m breaking down 10 practical, low-pressure ways to build emotional closeness that feel fun, natural, and mutual so you’re not stuck carrying all the weight of “going deep.” I’ll show you how to connect through shared experiences, create emotional safety, and build trust without forcing heavy conversations, plus why emotional intimacy is more than just talking about your feelings. You’ll also hear a listener Q&A on oversharing, one-sided connection, and giving things time to develop, a Dating Dilemma on whether “too slow” is a red flag, and a Text Support breakdown of when not to offer a second date.

LINKS MENTIONED:

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Welcome to part 1 of Comparing Notes, a new mini series I'm doing with my friend, Ali Jackson of Finding Mr. Height! This entire series will cover the different stages of a new relationship: what to expect, what to focus on and how to get through it with grace. In this episode, we're deep diving into the first 3 months of a new relationship, talking about our own experiences and providing tons of tips and actionable advice. Even if you're currently single, knowing what's to come can help you focus on the right things early on. You'll learn what we wish we knew when we were in new relationships and so much more.

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Maybe you’ve heard the advice to “date multiple people,” but you’re not sure how it actually works, if it’s even possible for you, or why you’d want to try it. In this episode, I’m sharing seven tips on how to approach dating multiple people before getting into a relationship. Multidating isn’t for everyone, but it works well if you're prioritizing dating, and it might be worth trying if you get attached quickly, want to speed up the vetting process, or are curious about a different way to date.

Plus, I’m answering a dating dilemma about what to do when you can’t shake the feeling that something is missing in a connection, even when everything else looks good on paper.

Here's the previous episode I mentioned about dating other people.

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In this episode, Dr. Caroline Leaf and I are bringing you the conversation about what it really means to “not be okay”, especially when it comes to dating and our mental health. We cover why sadness or anxiety doesn’t mean we’re broken, and how the pressure to be constantly happy or healed can actually make things worse. Caroline shared practical tools from her new book Help in a Hurry, including how to create a 63-second pause to calm spiraling thoughts and respond with more clarity and confidence. We also talked about how past dating experiences shape our beliefs and how to gently rewire those patterns over time. This conversation was such a powerful reminder that we all have the inner wisdom to navigate hard moments, and that growth starts by giving ourselves compassion.

Mentioned in this episode:

Caroline's book: Help in a Hurry: Simple Tips for Finding Peace When You're Overwhelmed, Anxious, or Stressed

My episode on The Dr. Leaf Show - “Mastering The Art Of Dating”

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Let's dive into how (and when) to take a real break from dating. If dating feels like a chore or if you're just emotionally tapped out, it just might be time to pull yourself out of the game to recover. In this episode, I'm walking you through how to take a break without feeling like you’re falling behind or sabotaging your chances of meeting someone. You'll learn signs it's time to reset, how to do it strategically and what to focus on while you're not dating. Additionally, I address your questions about oversharing, taking long breaks, and managing the fear of missing out. At the end, you'll hear a dating dilemma about dating someone who has to move for a job and a new segment called Dating Done Right.

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How To Identify Your Needs 1-hr Class

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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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