790. The Dating Advice No One’s Actually Giving You with Case Kenny

15 snips

Aug 21, 2025

In this engaging discussion, bestselling author Case Kenny shares insights on breaking dating patterns and redefining independence. He emphasizes the importance of learning from 'failed' relationships and embracing the chaos of modern dating. Listeners discover how to upgrade their emotional vocabulary and navigate attachment styles. Case advocates for playful mindfulness in partnerships and trusting the universe’s timing. Packed with practical tips, this conversation encourages self-awareness and living authentically in the quest for love.

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ADVICE

Use Past Promises To Spot Self-Betrayal

Compare current compromises to promises from past relationships to spot self-betrayal.
Use that comparison as a barometer before accepting situations that hurt you.

ADVICE

Say When You Don't Feel Loved

Have the hard conversation: "I know you love me, but I don't feel loved."
Ask how you want to be loved and remove ego from the exchange to improve connection.

ANECDOTE

Gifts Missed The Mark Until Honest Feedback

Case kept gifting books to his partner as his love language until she honestly asked him to stop.
That candid moment proved they could be honest and changed his view of intimacy.

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In this episode, Lindsey sits down with bestselling author Case Kenny for a raw convo about breaking dating patterns, redefining independence, and manifesting love that meets you on your level. You’ll rethink everything you know about dating, partnership, and self-worth with this one!

Ahead, Case gets real about the messy magic of modern relationships + the lessons hidden in those “failed” loves that move us forward. Case urges that those chaotic, cringey, or lonely moments are shaping you into the woman you’re meant to become. (Yes, we get spiritual about it.)

Whether you’re a self-help junkie, serial dater, or in a forever mood with your partner, this episode will have you journaling, laughing, and maybe re-downloading that app. If you’re ready to release the pressure and fall in love, tune in and get Case’s new book, The Opposite of Settling, out now!

We also talk about:

How to upgrade your emotional vocabulary
The difference between expectations + standards
Flipping the script on anxious + avoidant attachment
Practical tips for calling in conscious, aligned love
The power of “chaos” + doing the opposite of what’s expected
Playfulness + humor as spiritual practices in partnership
How to know if your relationship is amplifying your true self
Letting go of timelines + trusting the universe’s bigger plan
What “building a life you love” actually looks like

Resources:

Order Case’s new book, The Opposite of Settling, out now
Instagram: @case.kenny
Website: https://www.casekenny.com/

Get our book, Almost 30: A Definitive Guide To A Life You Love For The Next Decade and Beyond, here: http://bit.ly/Almost30Book.

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Almost 30 is edited by Garett Symes and Isabella Vaccaro.

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