128. Communicating Your Needs, Starting Deep Conversations & Lifestyle Dealbreakers

128. Communicating Your Needs, Starting Deep Conversations & Lifestyle Dealbreakers

In this episode, I'm answering three dating questions from listeners dealing with confusing behavior, imbalances in a relationship, and uncertainty about moving forward in a new situation. I love answering your questions!


  • We had five dates. Then he left for a work trip. I haven't heard from him. What to do?
  • I'm the only one who brings up deep conversations in my relationship. Can I ask him to start initiating them more?
  • I'm starting to realize my date is a big drinker and I'm not. How to end it?

  • As always I'd love to hear your thoughts in the comments if you're listening on Spotify! '


    Get 15% off Jenni Kayne this holiday season! Use code DATING15 at checkout. https://www.jennikayne.com/


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    Watch on YouTube: https://youtu.be/eozMHfkBgA0


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    My Identify Your Needs course: http://bit.ly/4e2nwGC


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    Read more on the blog: https://intentionally.dating/blog-posts/


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    #datingadvice #datingtips #dating

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    Avsnitt(261)

    239. Singles Events, Setups & Lessons From Vetting 800 Men w/ Alli Goldberg

    239. Singles Events, Setups & Lessons From Vetting 800 Men w/ Alli Goldberg

    Alli Goldberg (back for round 2!) is the creator and host of Love Isn't Blind, the live dating show where the men can't speak, and she's now hosted nearly 100 shows across 10 cities. That means she's ...

    20 Feb 49min

    238. When to Say "I Love You" (And Should You Say It First?)

    238. When to Say "I Love You" (And Should You Say It First?)

    I'm sharing my experiences with saying "I love you" for the first time, from awkwardly blurting it out in a noisy subway station to intentionally saying it over the phone. I'm covering the signs you'r...

    17 Feb 26min

    237. Surviving the Worst Parts of Dating w/ Rory Uphold

    237. Surviving the Worst Parts of Dating w/ Rory Uphold

    I'm chatting with Rory Uphold, a writer and the author of The Final Girl's Guide to the Horrors of Dating, a book that uses the horror movie framework to help people navigate modern dating. We're disc...

    13 Feb 57min

    236. When to Move In (And What No One Tells You About Living Together)

    236. When to Move In (And What No One Tells You About Living Together)

    You know you want to be with your partner for a long time, but how do you know when to move in? Today I'm sharing everything I've learned about moving in with a partner, from knowing when you're ready...

    10 Feb 34min

    235. Dating Red Flags That Predict Domestic Inequity w/ Laura Danger

    235. Dating Red Flags That Predict Domestic Inequity w/ Laura Danger

    Author and educator Laura Danger (@thatdarnchat) brought weaponized incompetence and the nag paradox into the mainstream, and today she's here to talk about how these dynamics can show up way before y...

    6 Feb 53min

    234. "His Best Friend Is A Woman. Is That A Red Flag?"

    234. "His Best Friend Is A Woman. Is That A Red Flag?"

    Feeling uneasy about your partner's friendship with someone of the opposite sex? You're not alone. In this episode, I'm breaking down what that jealousy actually means, when it's a you problem vs. a r...

    3 Feb 24min

    233. Why You Obsess Over Someone You Barely Know w/ Sabrina Bendory

    233. Why You Obsess Over Someone You Barely Know w/ Sabrina Bendory

    Sabrina Bendory, author of Detached: How to Let Go, Heal and Become Irresistible, joins me to break down what detached dating actually means (hint: it's not about not caring). We get into why you keep...

    30 Jan 56min

    232. Are You Staying for the Right Reasons? (Dating Dilemmas)

    232. Are You Staying for the Right Reasons? (Dating Dilemmas)

    I'm answering four real dating dilemmas from listeners stuck on whether to stay or leave a relationship. I get into how to end a medium-term relationship, what to do when you've been on the fence for ...

    27 Jan 34min

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