
Creating Confidence with Heather Monahan
#520 What He’s Really Thinking in the First 3 Dates: Flirting, Communication & Navigating the Early Days of Dating with Dating Strategist Ben Hart
13 May 2025
If you’ve ever felt like dating is one giant mystery while every other area of your life has a strategy—this episode is your game-changer. I’m joined by dating strategist Ben Hart, and we’re breaking down how to stop sitting on the sidelines and start approaching your love life with the same intention, confidence, and momentum you bring to your career. From how to stop overthinking early dating stages to setting standards without pushing love away, this conversation will help you flip the script on dating and attract the kind of relationship you actually want. In This Episode You Will Learn Dating requires intention, just like any other life goals. The small confidence-building steps that matter more than grand gestures. Why creating fictional narratives is killing your relationships. Practical tips for flirting and navigating the early stages of a new relationship. Stop treating dating as a transaction, enjoy the process and yourself. Resources + Links Sign up for a one-dollar-per-month trial period at shopify.com/monahan Download the CFO’s Guide to AI and Machine Learning at NetSuite.com/MONAHAN. Want to do more and spend less like Uber, 8x8, and Databricks Mosaic? Take a free test drive of OCI at oracle.com/MONAHAN. Get 10% off your first Mitopure order at timeline.com/CONFIDENCE. Get 15% off your first order when you use code CONFIDENCE15 at checkout at jennikayne.com. Call my digital clone at 201-897-2553! Visit heathermonahan.com Sign up for my mailing list: heathermonahan.com/mailing-list/ Overcome Your Villains is Available NOW! Order here: https://overcomeyourvillains.com If you haven't yet, get my first book Confidence Creator Follow Heather on Instagram & LinkedIn Ben on Instagram
Full Episode
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I think that dating, specifically for a lot of people, is difficult because they've developed a structure around a lot of other aspects of their life, like their work and their school and their gym routines. There's a lot of structure associated with it. You do X, you get Y. And I think that with dating, there's not a lot of structure. A lot of people have this really unique Disney...
fairy tale attached to how it should happen. And not a lot of people actually like to think about dating so strategically. And I get, I get why it's not an attractive thing to be like, Oh, what do you mean? I got to do this, this, and this. I'm like, well, you don't have, no, you don't have to do anything.
But if you think about it a little bit more strategically without focusing on the hard truths of the details, just strategically framework. And then like, think about how to progress that aspect of your life. Like, you know, if you don't think about dating or dating fundamentally with more purpose or more intention, then I don't, I don't see how you just expect things to happen.
Come on this journey with me.
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