Dating Intentionally

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. Join my new boundaries workshop on Monday, 8/18! Get free shipping on affordable bedding from Quince CONNECT WITH ME: Ask a question for me to answer on the pod Slide into my DMs on IG @dating.intentionally! MORE FREE ADVICE: Free texting templates & dating FAQ guide Get more dating advice from me on YouTube Dating Intentionally on TikTok Read more on the blog DATING COURSES Swipe, Match, Date - Master The Dating Apps How To Identify Your Needs 1-hr Class SUPPORT THE POD Rate on Apple Learn more about your ad choices. Visit megaphone.fm/adchoicesSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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” CONNECT WITH ME: Ask a question for me to answer on the pod Slide into my DMs on IG @dating.intentionally! MORE FREE ADVICE & CONTENT Free texting templates & dating FAQ guide Get more dating advice from me on YouTube Dating Intentionally on TikTok Read more on the blog DATING COURSES Swipe, Match, Date - Master The Dating Apps How To Identify Your Needs 1-hr Class SUPPORT THE POD Rate on Apple Learn more about your ad choices. Visit megaphone.fm/adchoicesSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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. CONNECT WITH ME: Ask a question for me to answer on the pod Slide into my DMs on IG @dating.intentionally! MORE FREE ADVICE & CONTENT Free texting templates & dating FAQ guide Get more dating advice from me on YouTube Dating Intentionally on TikTok Read more on the blog DATING COURSES Swipe, Match, Date - Master The Dating Apps How To Identify Your Needs 1-hr Class SUPPORT THE POD Rate on Apple Learn more about your ad choices. Visit megaphone.fm/adchoicesSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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 PARTNERS! ⁠⁠⁠⁠⁠Get an extended free trial of Dipsea!⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠Get a discount on your Galatea membership!⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠Mint Mobile: Get your summer savings and shop premium wireless plans!⁠⁠⁠⁠ CONNECT WITH ME: ⁠⁠⁠⁠Ask a question for me to answer on the pod⁠⁠⁠⁠ ⁠⁠⁠⁠Slide into my DMs on IG @dating.intentionally!⁠⁠⁠⁠ MORE FREE ADVICE & CONTENT ⁠⁠⁠⁠Free texting templates & dating FAQ guide⁠⁠⁠⁠ ⁠⁠⁠⁠Get more dating advice from me on YouTube⁠⁠⁠⁠ ⁠⁠⁠⁠Read more on the blog⁠⁠⁠⁠ DATING COURSES ⁠⁠⁠⁠Swipe, Match, Date - Master The Dating Apps⁠⁠⁠⁠ ⁠⁠⁠⁠How To Identify Your Needs 1-hr Class⁠⁠⁠⁠ SUPPORT THE POD ⁠⁠⁠⁠Rate on Apple⁠ Learn more about your ad choices. Visit megaphone.fm/adchoicesSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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 PARTNERS! ⁠⁠⁠⁠⁠Get an extended free trial of Dipsea!⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠Get a discount on your Galatea membership!⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠Mint Mobile: Get your summer savings and shop premium wireless plans!⁠⁠⁠⁠ CONNECT WITH ME: ⁠⁠⁠⁠Ask a question for me to answer on the pod⁠⁠⁠⁠ ⁠⁠⁠⁠Slide into my DMs on IG @dating.intentionally!⁠⁠⁠⁠ MORE FREE ADVICE & CONTENT ⁠⁠⁠⁠Free texting templates & dating FAQ guide⁠⁠⁠⁠ ⁠⁠⁠⁠Get more dating advice from me on YouTube⁠⁠⁠⁠ ⁠⁠⁠⁠Read more on the blog⁠⁠⁠⁠ DATING COURSES ⁠⁠⁠⁠Swipe, Match, Date - Master The Dating Apps⁠⁠⁠⁠ ⁠⁠⁠⁠How To Identify Your Needs 1-hr Class⁠⁠⁠⁠ SUPPORT THE POD ⁠⁠⁠⁠Rate on Apple⁠ Learn more about your ad choices. Visit megaphone.fm/adchoicesSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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 PARTNERS! ⁠⁠⁠⁠⁠Get an extended free trial of Dipsea!⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠Get a discount on your Galatea membership!⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠Mint Mobile: Get your summer savings and shop premium wireless plans!⁠⁠⁠⁠ CONNECT WITH ME: ⁠⁠⁠⁠Ask a question for me to answer on the pod⁠⁠⁠⁠ ⁠⁠⁠⁠Slide into my DMs on IG @dating.intentionally!⁠⁠⁠⁠ MORE FREE ADVICE & CONTENT ⁠⁠⁠⁠Free texting templates & dating FAQ guide⁠⁠⁠⁠ ⁠⁠⁠⁠Get more dating advice from me on YouTube⁠⁠⁠⁠ ⁠⁠⁠⁠Read more on the blog⁠⁠⁠⁠ DATING COURSES ⁠⁠⁠⁠Swipe, Match, Date - Master The Dating Apps⁠⁠⁠⁠ ⁠⁠⁠⁠How To Identify Your Needs 1-hr Class⁠⁠⁠⁠ SUPPORT THE POD ⁠⁠⁠⁠Rate on Apple⁠ Learn more about your ad choices. Visit megaphone.fm/adchoicesSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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  PARTNERS! ⁠⁠⁠⁠⁠Get an extended free trial of Dipsea!⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠Get a discount on your Galatea membership!⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠Mint Mobile: Get your summer savings and shop premium wireless plans!⁠⁠⁠⁠ CONNECT WITH ME: ⁠⁠⁠⁠Ask a question for me to answer on the pod⁠⁠⁠⁠ ⁠⁠⁠⁠Slide into my DMs on IG @dating.intentionally!⁠⁠⁠⁠ MORE FREE ADVICE & CONTENT ⁠⁠⁠⁠Free texting templates & dating FAQ guide⁠⁠⁠⁠ ⁠⁠⁠⁠Get more dating advice from me on YouTube⁠⁠⁠⁠ ⁠⁠⁠⁠Read more on the blog⁠⁠⁠⁠ DATING COURSES ⁠⁠⁠⁠Swipe, Match, Date - Master The Dating Apps⁠⁠⁠⁠ ⁠⁠⁠⁠How To Identify Your Needs 1-hr Class⁠⁠⁠⁠ SUPPORT THE POD ⁠⁠⁠⁠Rate on Apple⁠ Learn more about your ad choices. Visit megaphone.fm/adchoicesSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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. Learn more about your ad choices. Visit megaphone.fm/adchoicesSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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.  PARTNERS! ⁠⁠⁠⁠⁠Get an extended free trial of Dipsea!⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠Get a discount on your Galatea membership!⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠Mint Mobile: Get your summer savings and shop premium wireless plans!⁠⁠⁠⁠ CONNECT WITH ME: ⁠⁠⁠⁠Ask a question for me to answer on the pod⁠⁠⁠⁠ ⁠⁠⁠⁠Slide into my DMs on IG @dating.intentionally!⁠⁠⁠⁠ MORE FREE ADVICE & CONTENT ⁠⁠⁠⁠Free texting templates & dating FAQ guide⁠⁠⁠⁠ ⁠⁠⁠⁠Get more dating advice from me on YouTube⁠⁠⁠⁠ ⁠⁠⁠⁠Read more on the blog⁠⁠⁠⁠ DATING COURSES ⁠⁠⁠⁠Swipe, Match, Date - Master The Dating Apps⁠⁠⁠⁠ ⁠⁠⁠⁠How To Identify Your Needs 1-hr Class⁠⁠⁠⁠ SUPPORT THE POD ⁠⁠⁠⁠Rate on Apple⁠ Learn more about your ad choices. Visit megaphone.fm/adchoicesSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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 PARTNERS! ⁠⁠⁠⁠⁠Get an extended free trial of Dipsea!⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠Get a discount on your Galatea membership!⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠Mint Mobile: Get your summer savings and shop premium wireless plans!⁠⁠⁠⁠ CONNECT WITH ME: ⁠⁠⁠⁠Ask a question for me to answer on the pod⁠⁠⁠⁠ ⁠⁠⁠⁠Slide into my DMs on IG @dating.intentionally!⁠⁠⁠⁠ MORE FREE ADVICE & CONTENT ⁠⁠⁠⁠Free texting templates & dating FAQ guide⁠⁠⁠⁠ ⁠⁠⁠⁠Get more dating advice from me on YouTube⁠⁠⁠⁠ ⁠⁠⁠⁠Read more on the blog⁠⁠⁠⁠ DATING COURSES ⁠⁠⁠⁠Swipe, Match, Date - Master The Dating Apps⁠⁠⁠⁠ ⁠⁠⁠⁠How To Identify Your Needs 1-hr Class⁠⁠⁠⁠ SUPPORT THE POD ⁠⁠⁠⁠Rate on Apple⁠ Learn more about your ad choices. Visit megaphone.fm/adchoicesSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.