139. Rewiring the "What Ifs": Anxiety, Overthinking, and Perfectionism in Dating with Dr. Jennifer Wolkin

Coming up on this episode of Flirtations, we’re talking anxiety, overthinking, and perfectionism in dating!

You know that feeling when you replay every text, second-guess what you said on a date, or try so hard to show up as your “best self” that you forget to just be yourself?

Joining us for this conversation is Dr. Jennifer Wolkin. Dr. Jen is a neuropsychologist, writer, and ADHD advocate, here to help us make peace with our brains, understand ourselves a little bit more, and why we do think the things we do!

Inside the episode, we’ll hear about what happens in the brain when we’re overthinking, how perfectionism can sabotage connection, and where dating anxiety really comes from.

Dr. Jen shares simple practices for grounding yourself before a date, how we can reframe perfectionism and worry, and building self-compassion along the way.

This one is all about the neuroscience behind our emotions in dating and how we can not all anxiety and overthinking to run the show.

Alright Flirties, let’s take a breath, let go of the “what-ifs,” and meet Dr. Jen!

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About our guest: Dr. Jen, PhD, MFA, is a licensed psychologist, and Harvard-trained neuropsychologist. She founded a private practice with an appreciation that our mind, body, and brain are intimately intertwined and impacted by one another. She is also a writer, speaker, mindfulness practitioner, and mental health advocate.

Her first book, Quick Calm: Easy meditations to short-circuit stress using mindfulness and neuroscience, was published in 2021. Her next book about finding your ADHD Blueprint is forthcoming from Tarcher in 2026. She has her MFA in poetry, and has published in multiple literary journals, mostly writing what she likes to name "neuro-poetry."

Dr. Jen is in Menopause, and unabashedly neurodiverse.

You can connect with Dr. Jen on Instagram (ADHD Page/Personal Page)

Buy the book, Quick Calm: Easy Meditations

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.