Dating Intentionally

In this second installment of Comparing Notes, I sit down with Ali Jackson, host of Finding Mr. Height, to talk about what often comes up around the six-month mark in a relationship. We get into the real stuff: when to start having check-ins, how to tell if someone could be marriage material, and what it means to settle into comfort and routine without losing the spark. We also explore deal breakers, financial conversations, traveling together, navigating family dynamics, and handling your first conflicts. You'll also hear both of our experiences with this milestone!

Listen to Comparing Notes Pt 1 - all about the first 3 months of a relationship!

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Ok, but what does ENM really mean? In this episode, I talk with Claire Perelman, a sex therapist, about what ethical non-monogamy (ENM) actually is (and isn't). We talk about different types of ENM (polyamory, swinging, open relationships, solo poly etc), “ethical” matters (consent, clarity, agreements), and how jealousy, anxiety, and attachment styles show up in real life. Claire shares her path to ENM, why opening a relationship won’t save a broken one, and the difference between adding sexual variety vs. building additional romantic bonds. Claire shares tips on what to ask on first dates to vet for real ENM (vs. cheaters), sexual health norms, pacing to avoid emotional whiplash, and how to decide if this lifestyle fits your values and nervous system.

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In this episode, I delve into what it truly means to be “ready” to date vs ready for a relationship. There’s a big difference between, and most people confuse the two. I’ll share how to tell if you're ready to date or for a relationship (or both), what true dating readiness looks like, and why you don’t need to have every part of your life perfectly together before putting yourself out there. We’ll also talk about dating while still healing from a breakup, the myth of being “fully healed,” and the mindset shifts that make it easier to date with clarity and confidence. Plus, I’m sharing a practical checklist to help you gauge your own readiness and I answer listener questions about emotional availability and long-term intentions.

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Episodes mentioned:

QUESTIONS TO ASK YOURSELF

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In this episode, I break down the top 11 red-flag phrases to never ignore in early dating, what they really mean, how to spot them even when attraction is loud, and exactly what to say or do in the moment. If you've ever heard the classics like “I’m bad at texting,” “I don’t like labels,” “you’re too good for me,” and “I’m not looking for anything serious right now,” this one is for you. At the end, I answer a Dating Dilemma about a long-distance “is it me or is it them?” situation and close with YOUR dating wins in a new segment.

Episode mentioned: #175 - How To Write A Manifest w/ Matchmaker Maria

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⁠⁠Master The Dating Apps⁠⁠

⁠⁠How To Identify Your Needs ⁠

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I’m breaking down how to handle workplace crushes without risking your job or your peace of mind! I cover what the research says about how common office romances really are, why you should never date a boss or direct report, and the steps to take if you do want to pursue a crush at work, from grabbing a casual lunch to keeping it professional at the office. I also share my own story about dating at a summer job and answer a listener's dilemma about whether to shoot her shot with a coworker she clicked with at a conference.

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MORE FREE ADVICE & CONTENT

⁠Free texting templates & dating FAQ guide⁠

⁠Get more dating advice from me on YouTube⁠

DATING COURSES

⁠Master The Dating Apps⁠

⁠How To Identify Your Needs ⁠

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In this episode, I talk with writer and academic Kelly Coyne about intentional living, relationships, and what happens when traditional scripts around dating and marriage fall short. We explore women’s narratives, prenups, communication, gender norms, and the “quiet betrayals” that can erode long-term partnerships. From rethinking chivalry to building a circle of support, this conversation offers a fresh lens on creating sustainable, fulfilling relationships.

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Find Kelly on IG

Kelly's writing

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Ask a question for me to answer on the pod

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Free texting templates & dating FAQ guide

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DATING COURSES

Master The Dating Apps

How To Identify Your Needs

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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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Listen to episode 174 about new relationships/integration

Try the 36 love questions

Check out [The And] question cards - use code TALIA

Agape question app

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DATING COURSES

Swipe, Match, Date - Master The Dating Apps

How To Identify Your Needs 1-hr Class

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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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RELATED EPISODES:

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Free texting templates & dating FAQ guide

Get more dating advice from me on YouTube

DATING COURSES

Swipe, Match, Date - Master The Dating Apps

How To Identify Your Needs 1-hr Class

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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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Free texting templates & dating FAQ guide

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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

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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”

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

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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.