
38. Why F*ckboys are Boring and How to Not Chase in Dating with Ryan Sheldon
Explicit content warning
10/11/24 • 63 min
Today we're asking the question "what the heck is happening out there dating?!" with Ryan Sheldon, author of the new book, "F*ckboys are Boring: A Gay Man's Guide to Dating (for everyone)."
We'll take on the topic of the f*ckboy, how he dates, how you can spot him, and what you can do with your boundaries so you don't get emotionally caught up in their web! Unless you want to date the f*ckboy for some fun, in which case we have some tips for you, too!
Ryan also shares about his experiences dating both sexes, and what it was like coming out after dating women and making the transition to dating men, oye! We'll also talk about dating psychology here, getting into the mind of men and why they do what they do.
Intertwined in this conversation are tips and strategies for not chasing and allowing yourself to be calm, cool, and collected in the dating process - which worked for Ryan who is now dating someone that involves a meet cute moment in an Uber!
Finally, we conclude with Ryan's journey of body acceptance and how becoming comfortable in his own skin changed everything and lead to more fulfilling experiences and connections.
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!
About our guest: Ryan Sheldon is a nationally recognized influencer, brawn model, and advocate for the LGBTQIA+ community. He has been featured on the TODAY Show and in publications like Psychology Today, Seventeen, and Teen Vogue, among others. In his latest book, FUCKBOYS ARE BORING: A Gay Man's Guide to Dating (for everyone), Ryan shares hilarious, heartbreaking, and candid stories from his personal journey through modern dating. Drawing from his own experiences, he offers a refreshingly honest and supportive guide for those seeking real connections in an era dominated by swipe culture. You can follow Ryan on Instagram @RealRyanSheldon and TikTok @RealRyanSheldon. To get a copy of "Fuckboys are Boring," check out Amazon, Barnes & Nobles, or anywhere books are found!
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 and transform lives for greater healing and deeper connections.
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.
💗 Happy flirting!
Today we're asking the question "what the heck is happening out there dating?!" with Ryan Sheldon, author of the new book, "F*ckboys are Boring: A Gay Man's Guide to Dating (for everyone)."
We'll take on the topic of the f*ckboy, how he dates, how you can spot him, and what you can do with your boundaries so you don't get emotionally caught up in their web! Unless you want to date the f*ckboy for some fun, in which case we have some tips for you, too!
Ryan also shares about his experiences dating both sexes, and what it was like coming out after dating women and making the transition to dating men, oye! We'll also talk about dating psychology here, getting into the mind of men and why they do what they do.
Intertwined in this conversation are tips and strategies for not chasing and allowing yourself to be calm, cool, and collected in the dating process - which worked for Ryan who is now dating someone that involves a meet cute moment in an Uber!
Finally, we conclude with Ryan's journey of body acceptance and how becoming comfortable in his own skin changed everything and lead to more fulfilling experiences and connections.
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!
About our guest: Ryan Sheldon is a nationally recognized influencer, brawn model, and advocate for the LGBTQIA+ community. He has been featured on the TODAY Show and in publications like Psychology Today, Seventeen, and Teen Vogue, among others. In his latest book, FUCKBOYS ARE BORING: A Gay Man's Guide to Dating (for everyone), Ryan shares hilarious, heartbreaking, and candid stories from his personal journey through modern dating. Drawing from his own experiences, he offers a refreshingly honest and supportive guide for those seeking real connections in an era dominated by swipe culture. You can follow Ryan on Instagram @RealRyanSheldon and TikTok @RealRyanSheldon. To get a copy of "Fuckboys are Boring," check out Amazon, Barnes & Nobles, or anywhere books are found!
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 and transform lives for greater healing and deeper connections.
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.
💗 Happy flirting!
Previous Episode

Flirtini #2: Dating Tips if You're New to Dating or Unsure Where to Start
Maybe today you find yourself looking to date for the first or for the first time in a long time. Perhaps you're recently coming off an extended dating break or you're single again after a long term relationship. And you don't know where to start.
Flirty, I got you!
In this Flirtini, I've got a plethora of tips for where to even begin in dating!
First, I share five mindset practices that will help you immensely as you get back out there dating, but I'm not going to share them in the notes. You gotta listen! 😛
After that, I've got a few dating strategy starting points (for dating both on the apps and in person), and we'll wrap up with some ways you can stay focused, manage anxiety, and not go down the rabbit hole of chasing unavailable partners!
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!
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 and romantic connection - to take center stage and transform lives for greater healing and ultimately, a deeper connection with the self.
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.
💗 Happy flirting!
Next Episode

39. Breaking Cycles in Dating (and in life!) with Jessica Amos
In this episode of Flirtations, we're breaking cycles, y'all! Cuz you are what? A cycle breaker!
With our incredible guest for this conversation, mindfulness coach and TEDx speaker Jessica Amos, we’ll explore how to break free from three types of cycles that play out in our dating lives - and beyond.
First, we'll look at generational cycles, or the cycles that become familiar to us through our childhood. These cycles take hold because of how we are raised, they form by making observations of our surroundings growing up, and we can even inherit them! How do these cycles find their way into our dating lives and impact how we form relationships, how we attach, and how we love?
Also up for consideration are mindset cycles, or those thought patterns we get stuck in that can fuel self doubt and negative thinking. How do we develop these cycles and what can we do about it to have more mental and emotional liberation in our own minds?
Finally, we'll be getting into behavior cycles, or our patterns of action that sometimes have us make the same decisions that aren't the best for us, leading to repeat mistakes and "learning" the same lesson over and over. What can you do if you feel like you can't break free from yourself and your own behavior?
If you’ve ever felt stuck in a loop or struggled with patterns that seem impossible to break, I hope you'll stay right here as we learn how to embrace change, cultivate a more empowered version of ourselves - and break cycles!
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!
About our guest: Jessica Amos is a certified mindfulness teacher, coach, two-time TEDx speaker, and the founder of Stay with Yourself. With over 1.2 million downloads and a community of 90,000 students, she blends personal storytelling with high-value courses on topics like Shadow Work, Inner Child Healing, and Compassionate Boundaries to create a safe, intimate space for healing. When she’s not writing, speaking, or working with clients, you can find her rocking out to Nirvana, taking obscenely long walks (is all day ever too long?) and planning her next escape from the internet. Learn more at StayWithYourself.com.
Get Jessica’s 10x Course Bundle ($49) - https://staywithyourself.circle.so/checkout/courses-bundle
Learn to Meditate in 8-Weeks with Jessica ($89) - https://staywithyourself.com/learntomeditate/
Join Jessica’s Intro to Inner Child Healing Workshop ($97) - https://www.autumnreeser.com/inner-child
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 and transform lives for greater healing and deeper connections.
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.
💗 Happy flirting!
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