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

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

Author: Krista Williams & Lindsey Simcik August 21, 2025 Duration: 1:15:52
Almost 30
HealthHealth & FitnessAlternativeEducationFitnessSelf Improvement
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.  Sponsors: Puori | Visit Puori.com/ALMOST30 and use our promo code ALMOST30 for 20% off.  Chime | Open your account in 2 minutes at chime.com/almost30. IQ Bar | Get 20% off all IQBAR products, plus get FREE shipping. Just text ALMOST to 64000 to get your discount. To advertise on this podcast please email: partnerships@almost30.com. Learn More: almost30.com/about almost30.com/morningmicrodose almost30.com/book Join our community: facebook.com/Almost30podcast/groups instagram.com/almost30podcast tiktok.com/@almost30podcast youtube.com/Almost30Podcast Podcast disclaimer can be found by visiting: almost30.com/disclaimer.  Almost 30 is edited by Garett Symes and Isabella Vaccaro. Learn more about your ad choices. Visit megaphone.fm/adchoices

Hosted by best friends Krista Williams and Lindsey Simcik, Almost 30 feels like a series of candid, late-night talks with people who genuinely get it. This podcast centers on the messy, transformative journey of navigating your late twenties and beyond, blending heart-centered conversations between the hosts with raw and impactful interviews. Their discussions naturally span modern spirituality, practical health and wellness, fitness, self-improvement, and the complexities of dating and relationships. What you’ll hear isn’t prescriptive advice but rather shared exploration-hilarious, vulnerable, and often surprising. The aim is to create a supportive audio space that challenges listeners to expand their view of what’s possible for their lives. Tuning into this podcast means joining a conversation that fuels a more conscious evolution, offering both laughter and tangible insights for personal growth. Krista and Lindsey build each episode with the intention to empower, making the often-isolating topics of alternative health and personal development feel accessible and deeply relatable.
Author: Language: English Episodes: 100

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Almost 30
Podcast Episodes
863. Rewire Beauty Conditioning + Actually Enjoy The Body You Have [not-audio_url] [/not-audio_url]

Duration: 55:01
In this episode, K+L unpack the body image conditioning many women carry from their twenties into adulthood. From dieting, comparison, and dating insecurities to confidence, pregnancy, and healing, this conversation refr…
862. I’m Pregnant with Baby #2! An Unfiltered Update + Q&A [not-audio_url] [/not-audio_url]

Duration: 40:07
Maybe you guessed it?! Lindsey is pregnant with baby #2! In this episode, she shares her exciting news and gets real about the emotional, physical, and spiritual shifts of pregnancy the second time around—from body image…
860. Identity Shifts, Breakups + Becoming Your Next Self [not-audio_url] [/not-audio_url]

Duration: 1:13:06
What if you could start over—right now? In this K+L solo, Lindsey + Krista explore the truth about identity shifts, the discomfort of being in-between versions of yourself, and why the most painful seasons are often the…
859. Why You Still Feel Stuck in Love (Even After Doing the Work) [not-audio_url] [/not-audio_url]

Duration: 1:56:27
If you’ve done the therapy, read the books, regulated your nervous system…and still feel stuck in the same relationship patterns—this is for you. Thais Gibson, counselor, speaker, and the co-founder of The Persona Develo…
858. Social Media as Shadow Work—What Your Triggers are Revealing [not-audio_url] [/not-audio_url]

Duration: 1:01:30
What if social media isn’t ruining your confidence… but revealing the exact places you’re meant to heal? In this deeply honest solo, Krista breaks down how your Instagram feed is actually a mirror—reflecting your fears,…
857. From Burnout to Desire: Reclaiming Your Body + Sex Life [not-audio_url] [/not-audio_url]

Duration: 1:28:19
In this episode, Krista sits down with world-renowned relationship therapist, media personality, award winning radio host, and New York Times bestselling author Laura Berman to unpack what’s really happening in modern lo…

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