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Knowing when to end a relationship is tricky, especially if there’s no glaring dealbreaker—sometimes, it’s just not the right fit. How do you know when it’s time to move on?
In this episode, I’m breaking down how to decide whether to keep dating someone or walk away, whether you’re just a few dates in or have been in a relationship for years. I’ll share tips for recognizing signs that it’s over, how to decide with compassion and practical advice for breaking things off based on where you are in your dating journey. I also share my personal experience and exact scripts to start the break up conversation.
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Episodes mentioned:
Ep 93: Why you need momentum in early dating (and how to create it)
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In this episode, I’m answering your dating dilemmas. Listen and get my take on these relatable dating scenarios and questions:
1. "If I'm so amazing (his words) why won't he date me?”
2. “I said we should just be friends, but now I’m interested in more.”
3. “How do I handle bad dating advice from family and friends?”
We also have an update from last week's episode from the woman who found out about her date's divorce before he told her.
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How long is the honeymoon phase supposed to last? Is it okay if we run into unsolvable issues in our relationship? What's an okay unsolvable issue, and what's not? These are some of the big questions my guest, Jordan Dann, explores in this episode. We also discuss the progression of new relationships and dealing with big differences. Jordan provides tips on how to get out of your head, stop constantly checking in, and navigate big challenges you may discover in the dating process. At the end, we talk about season 7 of Love Is Blind.
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Jordan Dann is a passionate and dynamic psychoanalyst, author, teacher, and speaker. With a rich background in Gestalt therapy, Somatic Experiencing, and Imago Relationship Therapy, she has honed her skills in helping individuals become more relational, self-aware, and emotionally expressive. Her earlier career as a coach and director for actors further fueled her desire to guide people toward authentic self-expression and freedom in their lives.
For over 20 years, Jordan dedicated herself to coaching professionals in the nonprofit sector, fostering environments where creativity, communication, and conflict resolution can thrive. She’s committed to helping individuals and teams achieve deeper fulfillment, effectiveness, and joy in their work.
As the author of "Somatic Therapy for Healing Trauma" and creator of the Relationship Transformation School, Jordan brings her expertise to those seeking healing and personal growth. She serves as faculty at Gestalt Associates for Psychotherapy in Manhattan and is a nationally certified, New York State-licensed psychoanalyst with a private practice in New York City.
Follow her on Instagram @jordandann for insights and inspiration.
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In this episode, I'm answering your dating dilemmas. Listen and get my take on:
1. "How do I navigate being more sexually experienced than my date?"
2. "Why do women keep rejecting me like this?"
3. "He never told me he was divorced, but I found out about it online."
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In this episode, I get into whether you are asking too much of your partner or not. You’ll learn about how to know if you are asking for too much, why we need to communicate this, and what to do when sharing what you need from your partner. I also get into why someone might be worth it if they’re struggling to meet your needs but still trying. This episode is for you if you want to communicate your needs without feeling like you’re asking too much. And at the end, I answer a dating dilemma about getting back together with someone who wasn’t ready to commit, but now they say they are.
Episodes mentioned in this podcast:
#9 How to define and discuss relationship needs
#31 Love bombing vs genuine interest (how to tell)
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In this episode, you’ll hear from Dr. Morgan Anderson, a clinical psychologist and relationship coach. We talk about attachment theory, common misconceptions of attachment theory, and building a secure attachment style. You’ll hear about how Dr. Morgan helps clients become more secure in their relationships. And Dr. Morgan provides a ton of tips for people in relationships with the different attachment styles. At the end, we answer a dating dilemma about communicating your standards in relationships to see if you have similar capacities and values.
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About Dr. Morgan: Dr. Morgan Anderson is a clinical psychologist, leading attachment theory expert, and relationship coach. She is also the author of Love Magnet and host of the Let's Get Vulnerable podcast (5M+ downloads). Featured in Brides, Women's Health, Cosmopolitan, Popsugar, Elite Daily, and more.
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In this episode, I share tips for talking about money in early dating, how to navigate dating when one person earns a lot more than the other and my experience with creating a prenuptial agreement with my husband. I share questions to ask on a first date to start talking about money and tips for getting into deeper conversations as your relationship progresses. At the end, I answer a dating dilemma from a woman who's concerned about her date's earning potential.
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Ramit's podcast: https://podcasts.apple.com/us/podcast/money-for-couples/id1577864998
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In this episode, Johnny and I recap our wedding and honeymoon experience. We answer questions about our favorite parts of the wedding weekend, things that went wrong, challenges during the planning process and how we made our day special. Then we get into our honeymoon in Greece, what it was like to use a travel agent for the first time and our thoughts on traveling together for 11 days. I hope you enjoy this episode! Thanks so much for listening and for following our journey.
Travel agent we used: https://erosandpsyche.travel/
Wedding pics: https://www.instagram.com/p/DAiwYmhPN5A/?img_index=1
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I'm back from my wedding & honeymoon with some brand new episodes! This week, we're deep-diving into age gaps. What's a good age range to have when searching for a partner? How do you deal with judgment when dating someone way older/younger than you? And can it work if you're over 10 years apart in age? In this episode, you'll hear my advice on navigating age gaps and setting your age range and you'll hear from folks who have experience dating people over 10 years older than them.
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In this episode, you’ll hear from Alex Koren, my brother. We talk about how to approach dating in your 30s, moving on from relationships, and being yourself when dating. You’ll hear about how Alex is putting himself in situations where socializing is natural. And Alex shares what is important to him when messaging new women and going on dates. At the end, we do a “Why do men” segment and Alex shares what he wants to see more of in dating culture.
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Hello from Greece! I'm on my honeymoon and thought this would be a great week to share an essential Dating Intentionally episode in case you missed it (or need to hear it again). This episode originally aired in November 2023.
Are you grounded in dating? Listen and learn what staying grounded in dating even means and what happens when we get completely carried away. I'm also getting into how to slow the process down and stay grounded in reality as you get to know someone you like. At the end of the episode, I'm answering two listener emails.
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In this episode, you’ll hear from Shani Silver, a podcaster and author of A Single Revolution: Don't Look For a Match—Light One. We talk about singlehood, dating apps, and the balance between wanting to be single and wanting a partner. You’ll hear about how Shani changed her perspective on dating and being single. Shani also provides a ton of tips for folks who want to make connections without putting too much pressure on relationships. At the end, Shani shares what she wants to see more of in the dating world and what you can do to flip the script while dating.
Follow Shani on Instagram: https://www.instagram.com/shanisilver/
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About Shani: Shani Silver is an author and podcaster originally from Fort Worth, Texas. Her name is pronounced like “rainy” with a “sh.” Her book, A Single Revolution: Don't look for a match—light one, helps singles reframe singlehood to see its value and validity, for as long as we happen to be single. She is not an advocate for singlehood, she's an advocate for people being happy while single, and there is a difference. Her podcast, A Single Serving Podcast, launched in April of 2019 in the hopes of giving single women content that—for once—didn’t revolve around dating, and to support singles around the world in shedding the societal shame of singlehood. Shani has lived and dated in Austin, TX, Los Angeles, CA, Chicago, IL, Philadelphia, PA, and Brooklyn, NY. She currently lives in New Orleans. Following ten years of use, Shani permanently deleted her dating apps in January of 2019. She has loved her life ever since.
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In this episode, I answer five dating dilemmas from listeners. Thanks to everyone who submitted dating dilemmas!
How to date when you have a checklist and don't want to waste time
How to deal with crazy schedules in early dating
What to do when they suddenly end it, even though it was great
What to do when your date has no follow-through
How to deal with hot and cold behavior in early dating
And at the end, I included a new segment featuring {The And} question cards! Use code TALIA to get a discount on question card decks.
https://shop.theskindeep.com/collections/the-and-relationship-card-game
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In this episode, you’ll hear from Lily Womble, a feminist dating coach and author of Thank You More Please. We talk about being a decision maker in your love life, self trust, and digging deeper to find what you really want. You’ll hear about how Lily adapted essence based preferences in her work. And Lily provides a ton of tips for folks who want to see more success in their dating lives. We discuss Lily’s book and Lily reveals what inspired her to write it. At the end, Lily shares her thoughts on dating apps and what she wants to see more of in the current dating world.
Connect with Lily on IG: https://www.instagram.com/datebrazen/
Read Lily’s book: https://www.datebrazen.com/book Submit a dating dilemma: https://forms.gle/xCmAWvDPGJdr3rFz9
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About Lily: Lily Womble is sparking a feminist revolution in the way we date and find love. She was one of the top matchmakers in the U.S., but after setting up hundreds of dates, Lily realized that the answer to finding love was much deeper than a setup, and that the way we are taught to date is still stuck in the patriarchal dark ages. She founded her company, Date Brazen, in 2018 and has since helped hundreds of women create love lives that are epic, settle-proof, and joyful-as-hell with her intersectional feminist approach.
She changes lives daily on TikTok, Top 4 Relationship Podcast- The Date Brazen Podcast , and sold-out coaching programs world-wide. Her debut nonfiction advice book, Thank You, More Please: A feminist guide to breaking dumb dating rules and finding love, comes out in June 2024 with Legacy Lit. She lives in Brooklyn with her husband, Chris.
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It's my wedding week! In this episode, I discuss how to know/decide that your partner is the one - meaning the person you will be with long-term and/or get married to. Even if you don't want to get married, this episode will walk you through the factors of deciding if the person you're with is someone you want to be with for the long haul. I address the mistakes we make along the way when making this decision and the pressure we put on ourselves. I also talk about how I decided/knew my fiance was the one and why I don't believe there is just one person for everyone.
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In this episode, you’ll hear from Whitni Miller, a couples’ intimacy coach and sex educator. We talk about desire discrepancy, speaking up during sex, and keeping it spicy in the bedroom.
You’ll hear about how Whitni helps clients with different levels of desire start the conversation and work through it together. And Whitni provides a ton of tips for people pleasers who don’t want to fake orgasms anymore. At the end, we answer a dating dilemma about differing kinks and sexual likes early on.
Follow Whitni on IG: https://www.instagram.com/bde.moves/
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About Whitni: Whitni Miller, also known as Bde.moves, is a distinguished figure in Queer couples' intimacy coaching and sex education, boasting over four years of expertise in guiding individuals and couples toward authentic pleasure. Grounded in principles of radical self-acceptance and relational communication, Whitni fosters transformative experiences, empowering clients to embrace their desires with confidence.
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In this episode, you'll get advice for starting and maintaining a long-distance relationship. I included advice from listeners who have successfully dated someone long distance, as well as advice from my own experience doing long distance for a year in my last relationship. You'll hear about how it works in the early stages of dating and how to strengthen and develop a long-term relationship even when you live far away from each other.
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In this episode, you'll hear from Ella Dawson, a writer and author, talk about what it’s like dating after leaving an abusive relationship and being diagnosed with an STI. She has made it her mission to break the stigma around herpes and other STIs because they’re a lot more common than you’d think. In this episode, Ella explains how to bring up STIs in a way that won’t result in an awkward silence or breakup. Ella also shares her advice for anyone who has experienced or is experiencing an abusive relationship and what tools you can use to prevent another relationship like that. And we chat about Ella’s new book, But How Are You Really? and what inspired her to write a novel!
Connect with Ella: https://www.instagram.com/brosandprose/
Get Ella’s book, But How Are You Really? https://amzn.to/4cXmf2b
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About Ella Dawson: Ella Dawson is an NYC-based sex and culture critic whose work has been published by Elle, Vox, and Women’s Health, among others. She was once internet famous for having herpes, but that’s a whole other story. Ella is proudly bisexual, very anxious, and aspires to adopt a kitten. Follow her on social media and on Patreon as @brosandprose.
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I believe dating can be fun. In this episode, you'll hear eight different ways to enjoy the process more so you can stop deleting and redownloading dating apps every month. Some of these tips are practical, like tweaking your pre-date routine. And some tips are more about your mindset, like why you need to stop trying to be liked. I also included a bunch of the BEST date ideas according to you, the listeners. At the end, I answer a dating dilemma about what to do when someone says "let's be friends" after a few great dates.
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In this episode, you'll hear from Celia Gurney, a writer and creator who covers demisexuality and asexuality. We get into Celia's journey and how she discovered demisexuality, different resources that helped her along the way, and different levels of attraction. You'll hear about primary attraction vs. secondary attraction and how to approach dating if you need to develop an emotional connection first.
Read Celia's essay: https://mangoprism.com/where-are-all-the-boyfriends-i-was-promised/
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Celia Gurney is a writer, educator, improviser, and content creator who just spent two years in France, where she co-founded an improv comedy collective. Her essay about discovering and embracing demisexuality can be found at Mangoprism.com, and links to everything else are on her Instagram (@ceelia_later).
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