Flirtations! with Benjamin, the Flirt Coach

132. Small Talk Secrets: How to Spark Real Connection with Dr. Connie Wang

Coming up on this episode of Flirtations, we’re diving into a topic that makes so many of us squirm—small talk. 
Maybe you dread it, maybe you wonder what the point even is, or maybe you just want to know how to turn casual conversations into real connections.
To help us out, we're joined by Dr. Connie Wang, a dentist, creator of the Just a Quick Pinch podcast, and known online as the Small Talk Doc! Dr. Wang has made it her mission to show that small talk isn’t awkward filler—it’s a learnable skill that can transform the way we date, flirt, and connect.
In this episode, we’ll explore how to shift your mindset around small talk, how to practice it in real life, and how to move from surface-level chatter to meaningful connection—without the pressure. 
We’ll talk about small talk as a skill, how we can boost conversational confidence, and the little cues that make you instantly more engaging.
We’ll share ways to create engaging small talks, how to open them, close them, and strategies for asking questions that lead to connection.
So if you’ve ever wished small talk felt easier—or even fun—this one’s for you. 
Let’s get into it Flirties, and meet Dr. Wang!
Don't forget to subscribe, rate, and review Flirtations on your favorite podcast platform, and share this episode to spread BFE - big flirt energy, all over the world!
Enjoying the show and want to support my work? Buy the Flirt Coach a coffee!
Work with me!
Take the FREE Flirt Styles Quiz
Get INSTANT ACCESS to my anti-anxiety flirting and dating guide
Download my FLIRTING AND TEXTING CONVERSATION GUIDE
Grab my FREE Dating App Survival handbook
Book your 1:1 Flirting Audit
Ask the Flirt Coach
Dr. Connie Wang is a family dentist based out of Boston, Massachusetts! Prior to receiving her Doctorate of Dental Medicine, she received her Doctorate of Pharmacy from the University of Rhode Island. Her favorite degree of all however, is being a certified yapper. A self proclaimed personality hire & lover of all things communication, she is on a mission to make the world a little less lonely for each and every person.
Her social media content on TikTok and Instagram (@drconniewang) focuses on harnessing the power of small talk to become the most connected, confident, and happiest version of you possible. When she isn't yapping about yapping, she is still yapping on her own podcast called Just A Quick Pinch - a podcast for young healthcare providers that shares both communication pearls and the weekly pop culture news for listeners to make small talk with patients and coworkers.
And when she's not doing that she's probably "making returns" at TJMaxx and mysteriously ending up with another haul, to her husband and dog's surprise. Feel free to reach out on any platforms to connect, would love to chat about your communication/small talk/TJMaxx questions!
Flirt Coach interview on Just a Quick Pinch
About your host:  Benjamin is a flirt and dating coach sharing his love of flirting and BFE - big flirt energy - with the world! A lifelong introvert and socially anxious member of society, Benjamin now helps singles and daters alike flirt with more confidence, clarity, and fun!
As the flirt is all about connection, Benjamin helps the flirt community (the Flirties!) date from a place that allows the value of connection in all forms - platonic, romantic, and with the self - to take center stage.
Ultimately, this practice of connection helps flirters and daters alike create stronger relationships, transcend limiting beliefs, and develop an unwavering love for the self.
His work has been featured in Fortune, NBC News, The Huffington Post, Men's Health, and Yoga Journal.
You can connect with Benjamin on Instagram, TikTok, watch on YouTube, and stream the Flirtations Flirtcast everywhere you listen to podcasts (like right here!), and find out more about working together 1:1 here.

Flirtini #16: Tips for a First Date!

The Flirtinis are BACK and this one is all about "Tips for a First Date!"
Here's what you can expect from this Flirtini:
➡️  First date communication (planning the date and confirming the date)
➡️  What you can wear and dating mindset
➡️  Where you can go/what you can do for a date
➡️  How you can greet each other
➡️  Conversation tips/what to talk about
➡️  Strategies for different scenarios (what if they don't ask any questions, what if they won't stop talking)
➡️  How you can explore compatibility
➡️  How you can end the date (maybe you want a second date or maybe you don't!)
💗 Happy flirting! 💗
__________
Watch on YouTube (it's a two parter there):  First Date Tips Part 1 and Part 2!
Don't forget to subscribe, rate, and review Flirtations on your favorite podcast platform, and share this episode to spread BFE - big flirt energy, all over the world!
__________
Enjoying the show and want to support my work? Buy the Flirt Coach a coffee!
Work with me!
Take the FREE Flirt Styles Quiz
Get INSTANT ACCESS to my anti-anxiety flirting and dating guide
Download my FLIRTING AND TEXTING CONVERSATION GUIDE
Grab my FREE Dating App Survival handbook
Book your 1:1 Flirting Audit
Ask the Flirt Coach
About your host:  Benjamin is a flirt and dating coach sharing his love of flirting and BFE - big flirt energy - with the world! A lifelong introvert and socially anxious member of society, Benjamin now helps singles and daters alike flirt with more confidence, clarity, and fun!
As the flirt is all about connection, Benjamin helps the flirt community (the Flirties!) date from a place that allows the value of connection in all forms - platonic, romantic, and with the self - to take center stage.
Ultimately, this practice of connection helps flirters and daters alike create stronger relationships, transcend limiting beliefs, and develop an unwavering love for the self.
His work has been featured in Fortune, NBC News, The Huffington Post, Men's Health, and Yoga Journal.
You can connect with Benjamin on Instagram, TikTok, watch on YouTube, and stream the Flirtations Flirtcast everywhere you listen to podcasts (like right here!), and find out more about working together 1:1 here.
 

131. Beyond the Checklist: Values Based Dating with Kelsea Warren

Coming up on this episode of Flirtations, we’re talking values based dating with Kelsea Warren!
Picture this:  you date based on timing, chemistry, or pressure—like friends settling down or feeling like you’re running out of time. 
While this can all be very real, what if dating wasn’t about chasing a spark or checking boxes, and instead was about grounding yourself in your values? What if clarity on your values could not only help you choose a partner—but also prevent dating burnout, heartbreak, and the feeling of losing yourself in the process?
To explore this, we’re joined today by Kelsea Warren, back on the show! Kelsea helps individuals and businesses elevate wellbeing and prevent burnout by identifying and aligning with their core values and after this episode, I think values based dating just might be your next dating strategy.
We’ll talk about what dating values actually are, how they’re different from surface-level preferences, and why getting clear on them can shift your entire approach to love. We’ll explore how to bring values into the dating conversation without scaring someone off, and how to spot green flags that someone shares your values—even if they don’t say it directly.
So, whether you’re new to dating, stuck in patterns that don’t feel good anymore, or just craving more intentional connection, this episode will help you build relationships that align with who you are.
Alright Flirties, let’s do this, and meet Kelsea!
Don't forget to subscribe, rate, and review Flirtations on your favorite podcast platform, and share this episode to spread BFE - big flirt energy, all over the world!
Enjoying the show and want to support my work? Buy the Flirt Coach a coffee!
Work with me!
Take the FREE Flirt Styles Quiz
Get INSTANT ACCESS to my anti-anxiety flirting and dating guide
Download my FLIRTING AND TEXTING CONVERSATION GUIDE
Grab my FREE Dating App Survival handbook
Book your 1:1 Flirting Audit
Ask the Flirt Coach
About our guest:  Kelsea Warren is a coach, consultant, and speaker who specializes in burnout prevention. She has a master's degree in social work and is approaching candidacy for a Ph.D. in Industrial and Organizational Psychology. She is an expert in employee burnout and workplace values and uses that as the lens to help thousands of high achievers create and sustain aligned careers and organizations improve their employee experience.
Kelsea has 6+ years of experience consulting and has worked with hundreds of businesses and employees to operationalize their values for wellbeing. Before that, she spent 8+ years in mental health and working as a clinical therapist. Kelsea has an organic audience of 150k+ across social platforms, which has landed her collaborations and keynotes with brands like Urban Decay, Cox Communications, Association for Talent Development, and University of Arizona.
Kelsea is also an Air Force spouse of 12 years and a mom to 2 daughters.
A gift from Kelsea! Make sure to grab your FREE resources!  Workplace Values Assessment & Wellbeing Audit
Get to know your values with the FREE character strengths assessment:  https://www.viacharacter.org/.
About your host:  Benjamin is a flirt and dating coach sharing his love of flirting and BFE - big flirt energy - with the world! A lifelong introvert and socially anxious member of society, Benjamin now helps singles and daters alike flirt with more confidence, clarity, and fun!
As the flirt is all about connection, Benjamin helps the flirt community (the Flirties!) date from a place that allows the value of connection in all forms - platonic, romantic, and with the self - to take center stage.
Ultimately, this practice of connection helps flirters and daters alike create stronger relationships, transcend limiting beliefs, and develop an unwavering love for the self.
His work has been featured in Fortune, NBC News, The Huffington Post, Men's Health, and Yoga Journal.
You can connect with Benjamin on Instagram, TikTok, watch on YouTube, and stream the Flirtations Flirtcast everywhere you listen to podcasts (like right here!), and find out more about working together 1:1 here.

130. Friend Crushes with Jewel Hohman

Coming up on this episode of Flirtations, we’re diving into a topic that I know many of you wonder about, but don’t always say out loud:  friend crushes. 
You know the feeling—when someone who started out as “just a friend” suddenly makes your heart race, or when you catch yourself asking: could we be more?
To explore this fascinating—and sometimes complicated—dynamic, we’re joined by human connection enthusiast and host of the Socially Delightful podcast, Jewel Hohman. Together, we’ll explore everything from how to tell if a friend might like you back, to the best way to ask them out without making things weird. 
We’ll also get into some perhaps trickier questions—what if they don’t feel the same, what if people gossip, what if it stirs jealousy in your friend group, or what happens if the relationship ends?
But that’s not all! We’ll also look at platonic friend crushes (cuz those exist, too!), the role of vulnerability, the power of connection, why we should all be flirting a little bit more, and how we can do just that.
So if you’ve ever had a friend crush—or maybe you’re in the middle of one right now—this episode is for you. 
Let’s do this Flirties, and meet Jewel!
Don't forget to subscribe, rate, and review Flirtations on your favorite podcast platform, and share this episode to spread BFE - big flirt energy, all over the world!
Enjoying the show and want to support my work? Buy the Flirt Coach a coffee!
Work with me!
Take the FREE Flirt Styles Quiz
Get INSTANT ACCESS to my anti-anxiety flirting and dating guide
Download my FLIRTING AND TEXTING CONVERSATION GUIDE
Grab my FREE Dating App Survival handbook
Book your 1:1 Flirting Audit
Ask the Flirt Coach
About our guest:  Jewel Hohman is a connection expert with a degree in psychology and a pending master's in social work, combining Evidence-Based Self Help and the latest friendship research to help women in their 20s and 30s to build friendships that actually nourish them.
In a post-pandemic world, people are more disconnected and lonelier than ever. We're ALL craving more meaningful connection, but how to make it? How to confidently build friendships that support us? Let's unpack the science behind friendships that actually nurture us.
Learn more about Jewel on her website and follow @connectionwithjewel on all social media platforms!
About your host:  Benjamin is a flirt and dating coach sharing his love of flirting and BFE - big flirt energy - with the world! A lifelong introvert and socially anxious member of society, Benjamin now helps singles and daters alike flirt with more confidence, clarity, and fun!
As the flirt is all about connection, Benjamin helps the flirt community (the Flirties!) date from a place that allows the value of connection in all forms - platonic, romantic, and with the self - to take center stage.
Ultimately, this practice of connection helps flirters and daters alike create stronger relationships, transcend limiting beliefs, and develop an unwavering love for the self.
His work has been featured in Fortune, NBC News, The Huffington Post, Men's Health, and Yoga Journal.
You can connect with Benjamin on Instagram, TikTok, watch on YouTube, and stream the Flirtations Flirtcast everywhere you listen to podcasts (like right here!), and find out more about working together 1:1 here.

129. The Anxious/Avoidant Dynamic in Dating with Carly Ann

Coming up on this episode of Flirations, we’re joined by Carly Ann, a therapist and attachment expert, here to have a conversation with us about the anxious/avoidant dynamic in dating!
We’ll talk about why this duo happens so often in dating, how to spot the difference between lovebombing and genuine interest, are they avoidant or not interested, and how anxiety shows up in the dating process.
We’ll get into what to do when insecurities, self doubt, or attachment wounds try to pull us off track and how your attachment style and nervous system are connected.
We’ll explore the origins of our attachment styles, why it’s not only about your childhood and family dynamics, and even how our attachment styles are fluid, not fixed.
Finally, how to tell the difference between chemistry and compatibility, ways to build secure attachments with others and within ourselves, and some communication strategies for early dating.
So, whether you feel like you’ve experienced the anxious/avoidant dynamic before, are curious to learn more, or just need something to listen (hello!), this episode is for you.
Let’s do this, Flirties, and meet Carly Ann!
Don't forget to subscribe, rate, and review Flirtations on your favorite podcast platform, and share this episode to spread BFE - big flirt energy, all over the world!
Enjoying the show and want to support my work? Buy the Flirt Coach a coffee!
Work with me!
Take the FREE Flirt Styles Quiz
Get INSTANT ACCESS to my anti-anxiety flirting and dating guide
Download my FLIRTING AND TEXTING CONVERSATION GUIDE
Grab my FREE Dating App Survival handbook
Book your 1:1 Flirting Audit
Ask the Flirt Coach
About our guest:  Carly Ann is an integrative therapist who helps people who worry, overthink, and find themselves stuck in unhealthy relationship patterns. She supports those who feel anxious, fear abandonment, or find themselves overreacting, especially when it feels like they have already tried everything.
Carly Ann’s mission is to show people that they are not alone and they are not stuck. Through her work, she helps individuals stop feeling “crazy” and reconnect with the version of themselves they were always meant to be: content, secure, and confident, before life, criticism, or loneliness made them doubt who they are.
Work with Carly Ann:  21 Day Anxious to Secure Course, grab the Anxious Attachment Bundle, follow on Instagram, and Subscribe on YouTube.
About your host:  Benjamin is a flirt and dating coach sharing his love of flirting and BFE - big flirt energy - with the world! A lifelong introvert and socially anxious member of society, Benjamin now helps singles and daters alike flirt with more confidence, clarity, and fun!
As the flirt is all about connection, Benjamin helps the flirt community (the Flirties!) date from a place that allows the value of connection in all forms - platonic, romantic, and with the self - to take center stage.
Ultimately, this practice of connection helps flirters and daters alike create stronger relationships, transcend limiting beliefs, and develop an unwavering love for the self.
His work has been featured in Fortune, NBC News, The Huffington Post, Men's Health, and Yoga Journal.
You can connect with Benjamin on Instagram, TikTok, watch on YouTube, and stream the Flirtations Flirtcast everywhere you listen to podcasts (like right here!), and find out more about working together 1:1 here.
 

128. Connection vs. Attachment with Dr. Janine O'Brien

Coming up on this episode of Flirtations, we’re answering one of the biggest questions in dating! Are we actually connecting — or just attaching?
Joining us Dr. Janine O’Brien, a psychologist, educator, and trauma-informed relationship specialist, who helps people untangle their attachment patterns and build more secure, meaningful relationships.
We’ll unpack how to spot the difference between lovebombing and genuine interest, why we sometimes confuse intensity with intimacy, and the ways our attachment wounds show up in dating. 
We’ll also talk about the marathon first date, what it looks like when we rush through dating, and how to ease dating anxiety so connection comes first.
Finally, we’ll explore what it means to develop self-trust, why we don’t need to hold everyone accountable, and how we can spot emotional availability within others and within ourselves.
If you’ve ever found yourself anxiously replaying texts, feel like you keep making mistakes, are ready to just give up, or curious about dating again, this episode is for you. 
It’s for everyone, basically!
Alright Flirties, let’s do this, and meet Dr. Janine!
Don't forget to subscribe, rate, and review Flirtations on your favorite podcast platform, and share this episode to spread BFE - big flirt energy, all over the world!
Enjoying the show and want to support my work? Buy the Flirt Coach a coffee!
Work with me!
Take the FREE Flirt Styles Quiz
Get INSTANT ACCESS to my anti-anxiety flirting and dating guide
Download my FLIRTING AND TEXTING CONVERSATION GUIDE
Grab my FREE Dating App Survival handbook
Book your 1:1 Flirting Audit
Ask the Flirt Coach
About our guest:  Dr. Janine O'Brien is a licensed clinical psychologist, practice owner, and relationship coach.  She specializes in working with millennials navigating anxiety, people-pleasing, relationship challenges, tricky family dynamics, modern dating, attachment wounds and relational trauma.  Her approach blends depth and relatability, helping clients untangle the roots of their struggles while building the clarity and confidence to create the kind of connections they actually want.  At the heart of her work is the belief that everyone deserves to feel secure and confident in their relationships, including the one they have with themselves.
In addition to her therapy practice, Dr. O'Brien is currently developing a course that blends self-paced learning, group coaching, and community support designed to help insecurely attached individuals move toward secure embodiment in their dating and relationships.  She has also been featured in outlets such as Huffpost, Very Well Mind, and Bustle, and is passionate about making psychology and mental health resources accessible and holistic.
You can connect with Dr. O'Brien on her website and Instagram.
About your host:  Benjamin is a flirt and dating coach sharing his love of flirting and BFE - big flirt energy - with the world! A lifelong introvert and socially anxious member of society, Benjamin now helps singles and daters alike flirt with more confidence, clarity, and fun!
As the flirt is all about connection, Benjamin helps the flirt community (the Flirties!) date from a place that allows the value of connection in all forms - platonic, romantic, and with the self - to take center stage.
Ultimately, this practice of connection helps flirters and daters alike create stronger relationships, transcend limiting beliefs, and develop an unwavering love for the self.
His work has been featured in Fortune, NBC News, The Huffington Post, Men's Health, and Yoga Journal.
You can connect with Benjamin on Instagram, TikTok, watch on YouTube, and stream the Flirtations Flirtcast everywhere you listen to podcasts (like right here!), and find out more about working together 1:1 here.

127. Codependency in Dating with Vanessa Bennett

Coming up on this episode of Flirtations, we’re going into the world of codependency with Vanessa Bennett!
Vanessa is a licensed marriage and family therapist, a sought-after speaker, co-host of the hit podcast Cheaper Than Therapy, and author of the new book The Motherhood Myth. Her work shines a light on how generational trauma, societal expectations, and personal experiences shape the ways we show up in relationships.
We’ll get into the origins of codependence and the different ways it shows up, and how we can identify patterns of control, validation-seeking, and over-functioning (hi people pleasing!),  and move toward interdependence, self-trust, and authentic connection. 
In our conversation, we explore how codependency is rooted in a fear and can feel as gripping as addiction. You’ll hear about the link between attachment styles and codependent behaviors, as we break down the difference between healthy attachment vs. emotional dependence, sharing tools you can use to build relationships that feel supportive - without losing yourself.
So, whether you’ve dated from this place of feeling responsible for everyone else’s emotions, or found it hard to let go of someone even though you knew they weren’t good for you, this episode offers both clarity and a path toward healing.
Let’s get into it Flirties, and meet Vanessa!
Don't forget to subscribe, rate, and review Flirtations on your favorite podcast platform, and share this episode to spread BFE - big flirt energy, all over the world!
Enjoying the show and want to support my work? Buy the Flirt Coach a coffee!
Work with me!
Take the FREE Flirt Styles Quiz
Get INSTANT ACCESS to my anti-anxiety flirting and dating guide
Download my FLIRTING AND TEXTING CONVERSATION GUIDE
Grab my FREE Dating App Survival handbook
Book your 1:1 Flirting Audit
Ask the Flirt Coach
About our guest:  Vanessa Bennett, LMFT, is licensed depth psychotherapist, author, and facilitator devoted to the lifelong work of coming home to the Self. In her words:  “My approach blends depth psychology, archetypal wisdom, and embodied healing—but it’s also no-nonsense, rooted in lived experience, and grounded in truth. I believe healing isn’t about becoming someone new. It’s about remembering who you were before the world told you to be small.”
Vanessa leads immersive healing retreats, workshops, and custom curriculum-based programs for nonprofits and corporations and founded the Inner Compass Academy, where she trains and supervise coaches and therapists to integrate depth and embodiment into their work.
Her newest book, The Motherhood Myth, explores how patriarchy, capitalism, and generational trauma have shaped our narratives around parenting, partnership, and identity, and how we begin the process of coming home to ourselves.
You can follow Vanessa on Instagram and learn more about her work on www.vanessabennet.com.
About your host:  Benjamin is a flirt and dating coach sharing his love of flirting and BFE - big flirt energy - with the world! A lifelong introvert and socially anxious member of society, Benjamin now helps singles and daters alike flirt with more confidence, clarity, and fun!
As the flirt is all about connection, Benjamin helps the flirt community (the Flirties!) date from a place that allows the value of connection in all forms - platonic, romantic, and with the self - to take center stage.
Ultimately, this practice of connection helps flirters and daters alike create stronger relationships, transcend limiting beliefs, and develop an unwavering love for the self.
His work has been featured in Fortune, NBC News, The Huffington Post, Men's Health, and Yoga Journal.
You can connect with Benjamin on Instagram, TikTok, watch on YouTube, and stream the Flirtations Flirtcast everywhere you listen to podcasts (like right here!), and find out more about working together 1:1 here.

126. Hookup Culture Uncovered with Dr. Lisa Wade

Coming up on this episode of Flirtations, we’re joined by Dr. Lisa Wade, a sociologist, assistant professor at Tulane University, and the author of the landmark book American Hookup: The New Culture of Sex on Campus. 
Her groundbreaking research draws from the intimate, real voices of college students and reveals that hookup culture isn’t just about casual sex—it’s a social system with its own rules, hierarchies, and pressures.
We’ll explore how this culture took hold and the surprising ways it shapes how we all date and connect cuz we all know hookup culture isn’t limited to the college campus. We’ll also look at trends, like why Gen-Z is having less sex than previous generations, how gender and power dynamics still influence intimacy, and what might be replacing the hookup script.
So whether you’ve lived through hookup culture, opted out entirely, or are curious about how it’s evolving today—this is a conversation about desire, connection, and the cultural forces that shape both.
Let’s do this Flirties, and meet Dr. Wade!
Don't forget to subscribe, rate, and review Flirtations on your favorite podcast platform, and share this episode to spread BFE - big flirt energy, all over the world!
Enjoying the show and want to support my work? Buy the Flirt Coach a coffee!
Work with me!
Take the FREE Flirt Styles Quiz
Get INSTANT ACCESS to my anti-anxiety flirting and dating guide
Download my FLIRTING AND TEXTING CONVERSATION GUIDE
Grab my FREE Dating App Survival handbook
Book your 1:1 Flirting Audit
Ask the Flirt Coach
Watch on YouTube
About our guest:  Lisa Wade is an Associate Professor at Tulane University with appointments in Sociology and the Gender and Sexuality Studies Program. As a public-facing scholar, Lisa works to make her and others’ scholarship engaging to a public audience.
To this end, she is the author of American Hookup: The New Culture of Sex on Campus; an introduction to sociology titled Terrible Magnificent Sociology; a sociology of gender textbook, Gender: Ideas, Interactions, Institutions, with Myra Marx Ferree; and numerous research articles. Her newest book—a documentation of undergraduate social life during the pre-vaccine pandemic—will be published next year.
You can find her online at lisa-wade.com, on Instagram at @lisawadephd, and on Bluesky at @lisawade.bsky.social.
About your host:  Benjamin is a flirt and dating coach sharing his love of flirting and BFE - big flirt energy - with the world! A lifelong introvert and socially anxious member of society, Benjamin now helps singles and daters alike flirt with more confidence, clarity, and fun!
As the flirt is all about connection, Benjamin helps the flirt community (the Flirties!) date from a place that allows the value of connection in all forms - platonic, romantic, and with the self - to take center stage.
Ultimately, this practice of connection helps flirters and daters alike create stronger relationships, transcend limiting beliefs, and develop an unwavering love for the self.
His work has been featured in Fortune, NBC News, The Huffington Post, Men's Health, and Yoga Journal.
You can connect with Benjamin on Instagram, TikTok, watch on YouTube, and stream the Flirtations Flirtcast everywhere you listen to podcasts (like right here!), and find out more about working together 1:1 here.

125. Dating Beyond the Patriarchy and Asking for More with Lily Womble

Coming up on this episode of Flirtations, we’re joined by the marvelous Lily Womble—a feminist dating coach, former top matchmaker, host of the Date Brazen podcast and author of Thank You, More Please: A Feminist Guide to Breaking Dumb Dating Rules and Finding Love. 
Lily is on a mission to help us break free from the beliefs the patriarchy has embedded in our love lives—and to ask for more. 
In this conversation, we talk about what it means to date as a feminist. We explore everything from how the patriarchy shapes modern dating culture to why so many women feel like they're “too much” and “not enough” at the same time. 
We’ll hear about Lily’s experience dating as a self described late bloomer, we’ll unravel the tension between wanting to be chosen and choosing for ourselves, how you can overcome a scarcity mindset - thoughts like, “It’ll never happen for me!” - by harnessing the power of desire.
We also get into black cat energy, the male gaze, and flirting, of course!
So, whether you’ve ever felt behind in dating, struggled to believe you deserve more, or found yourself following traditional gender norms and yet it’s not for you - you’re going to want to hear this.
Let’s do this Flirties, and meet Lily!
Don't forget to subscribe, rate, and review Flirtations on your favorite podcast platform, and share this episode to spread BFE - big flirt energy, all over the world!
Enjoying the show and want to support my work? Buy the Flirt Coach a coffee!
Work with me!
Take the FREE Flirt Styles Quiz
Get INSTANT ACCESS to my anti-anxiety flirting and dating guide
Download my FLIRTING AND TEXTING CONVERSATION GUIDE
Grab my FREE Dating App Survival handbook
Book your 1:1 Flirting Audit
Ask the Flirt Coach
Watch on YouTube
About our guest:  Lily Womble was one of the top matchmakers in the U.S. After setting up hundreds of first dates, she realized that with the right tools, high achieving women could match themselves better than anyone else ever could.  She started her company, Date Brazen, five years ago and has since helped thousands of women become their own expert matchmaker with her unconventional, intersectional feminist approach to dating.  She's on a mission to interrupt the patriarchal status quo found in the dating world to help women create love lives that are self-trust filled, settle-proof, and actively joyful.  
She changes lives daily with her 85k+ TikTok community, Top 4 Relationship Podcast- The Date Brazen Podcast- , and sold-out coaching programs world-wide. She lives in Brooklyn with her fiancé, Chris.
You can find out more about working with Lily here, buy Thank You, More Please, follow Lily on Instagram, TikTok, and YouTube, and stream the Date Brazen podcast.
About your host:  Benjamin is a flirt and dating coach sharing his love of flirting and BFE - big flirt energy - with the world! A lifelong introvert and socially anxious member of society, Benjamin now helps singles and daters alike flirt with more confidence, clarity, and fun!
As the flirt is all about connection, Benjamin helps the flirt community (the Flirties!) date from a place that allows the value of connection in all forms - platonic, romantic, and with the self - to take center stage.
Ultimately, this practice of connection helps flirters and daters alike create stronger relationships, transcend limiting beliefs, and develop an unwavering love for the self.
His work has been featured in Fortune, NBC News, The Huffington Post, Men's Health, and Yoga Journal.
You can connect with Benjamin on Instagram, TikTok, watch on YouTube, and stream the Flirtations Flirtcast everywhere you listen to podcasts (like right here!), and find out more about working together 1:1 here.

124. The Subconscious Mind and Reprogramming Limiting Beliefs with Natalie Stavola

Coming up on this episode of Flirtations, we’re going straight to the source of transformation—the subconscious mind.
Joining us for this conversation is Natalie Stavola, a certified hypnotherapist, coach, author, and speaker with a deeply personal story of healing—from addiction and self-sabotage to empowerment and purpose. 
Natalie helps people rewire limiting beliefs, release emotional blocks, and rebuild the self-trust needed to experience relationships based on truth rather than pain.
Inside the episode, we’ll learn why your subconscious mind might be the very thing keeping you from what you want and how our earliest programming creates the beliefs we carry into adulthood.
We’re talking about what it means to date while stuck in survival mode, how shame and self-doubt can sabotage connection, how to identify our limiting beliefs, and finally, how to reprogram them.
If you’re ready to stop asking all the questions and instead start listening to yourself again… this one is for you. 
Let’s do this, Flirties, and meet Natalie!
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About our guest:  Natalie Stavola is a globally recognized career and dating coach who has helped over 3,000 people worldwide transform their lives. Known for her direct yet compassionate style, she specializes in helping men—especially those entering or navigating positions of power—develop emotional intelligence, shift internal power dynamics, and break free from limiting beliefs.
Certified in Neuro-Linguistic Programming (NLP), coaching, and a degree in Psychology and Communications, Natalie empowers clients to access deeper self-worth, improve communication, and thrive in both their professional and romantic lives. Her coaching techniques have consistently produced fast, lasting results, attracting high-achieving individuals from all walks of life. She is also a #1 Amazon New Release author in the dating and relationships category.
You can follow Natalie on Instagram, work with Natalie 1:1, and schedule a FREE 60 minute discovery call. 
About your host:  Benjamin is a flirt and dating coach sharing his love of flirting and BFE - big flirt energy - with the world! A lifelong introvert and socially anxious member of society, Benjamin now helps singles and daters alike flirt with more confidence, clarity, and fun!
As the flirt is all about connection, Benjamin helps the flirt community (the Flirties!) date from a place that allows the value of connection in all forms - platonic, romantic, and with the self - to take center stage.
Ultimately, this practice of connection helps flirters and daters alike create stronger relationships, transcend limiting beliefs, and develop an unwavering love for the self.
His work has been featured in Fortune, NBC News, The Huffington Post, Men's Health, and Yoga Journal.
You can connect with Benjamin on Instagram, TikTok, stream the Flirtations Flirtcast everywhere you listen to podcasts (like right here!), and find out more about working together 1:1 here.