827. Why Dating Feels Harder Than Ever Today (+ The Mindset Shifts You Need)

Almost 30

Krista Williams & Lindsey Simcik

Alternative Health, Self-improvement, Health & Fitness, Education

4.5 • 4K Ratings

🗓️ 16 December 2025

⏱️ 68 minutes

🔗️ Recording | iTunes | RSS

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Summary

In this episode, K+L sit down with relationship expert, bestselling author, and acclaimed pastor Stephen Chandler. From the influence of dating apps + social media to what’s really holding people back from finding a partner, Stephen breaks down the mindset shifts you NEED for true love. Ahead, Stephen reveals empowering strategies for women to attract high-quality partners, how to deal with financial expectations, and why long-lasting love starts with crystal-clear self-awareness. Stephen also shares his own marriage insights + shocking truths about choosing the “one.” Stephen tackles some of the biggest questions of your dating life: when to have the “serious talks,” whether you can change someone, and the surprising ways childhood patterns affect your adult relationships. If you want to know what’s missing from today’s dating landscape, this one’s for you! We also talk about: Why so many relationships end because of dopamine addiction The truth about finances + work ethic in a partner How to figure out if your personal values (really) align The role of discipline + boundaries around sex before marriage—beyond just religion Why women are out-earning + out-growing the current dating pool How childhood + generational trauma shows up in your love life + commitment fears Setting a clear “dating timeline” so you don’t waste your time Powerful tips for not falling into the trap of rescuing or “fixing” a partner The importance of taking action (not just praying or hoping) to meet your person The difference between net worth + true legacy when building your dream life Resources: Website: https://www.stephenrchandler.com/ Book: Relationship Road Map: Step-By-Step Directions to Finding Your Spouse (Jan. 21, 2025) Instagram: @stephenrchandler TikTok: @stephenrchandler_ YouTube: weareunionchurch Facebook: stephenrchandler X: pastorstephen_ Order our book, Almost 30: A Definitive Guide To A Life You Love For The Next Decade and Beyond, here: https://bit.ly/Almost30Book. Sponsors: LMNT | Go to DrinkLMNT.com/ALMOST30 and get a free sample pack with any order. That’s 8 single serving packets FREE with any LMNT order. Ka’Chava | Go to kachava.com and use code ALMOST30 for 15% off your next order. SKIMS | Shop my favorite bras and underwear at SKIMS.com/almost30. Hero Bread | Hero Bread is offering 10% off your order. Go to hero.co and use code ALMOST30 at checkout. Revolve | Shop at REVOLVE.com/ALMOST30 and use code ALMOST30 for 15% off your first order. #REVOLVEpartner Aura Frames | Visit AuraFrames.com and get $45 off Aura’s best-selling Carver Mat frames by using promo code ALMOST30 at checkout. To advertise on this podcast please email: partnerships@almost30.com. Learn More: https://almost30.com/about https://almost30.com/morningmicrodose https://almost30.com/book Join our community: https://facebook.com/Almost30podcast/groups https://instagram.com/almost30podcast https://tiktok.com/@almost30podcast https://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

Transcript

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0:00.0	Hello and welcome to Almost 30 podcast.
0:16.7	Hi everybody. Welcome to the show. It's Lindsay and Krista. Getting cozy here in New York.
0:20.9	Getting cozy here in New York. We're back and we're really excited to have Steven Chandler on talking relationships and dating. I love the energy in this one. Oh, my gosh. I was on, I was just, sometimes you got to like push and carry the energy. This one, I felt like I was on a good, good fun ride. Yes. How many times our boy said, I'm going to get in trouble for this one.
0:41.4	I'm going to get in trouble for this one. I was like, clip it. I was like, that's the viral hook that we need.
0:47.3	Clip it. It was so much fun. We talked about dating. His new book, The Relationship Roadmap, is an incredible guide for
0:56.3	singles. What I thought was really interesting and just one of like the notable quotes or
1:03.3	themes from the book is that a lot of relationship or a lot of marriage issues is not like a marriage
1:09.1	issue itself. It's really stemming back to behavior or beliefs when you were single.
1:14.9	And so taking very seriously this period of being single will benefit your relationships.
1:22.6	What's an example of that?
1:36.6	I think I've experienced this where in my relationship, if I felt there was a disconnect between a disconnect in communication or like the other person like understanding me or
1:43.9	knowing what I want, If I could trace it
1:47.2	back when I was single, that to me was never really clear. What do I really, really want?
1:54.7	Yeah. And was I actually one, honest with myself and clear with myself, and also was I communicating it or picking that
2:03.5	in my dating life? And I was kind of doing the opposite, if I'm being honest. I know. It's so
2:09.5	interesting because I think there's one side of it that's like, you know, you want to stay open,
2:14.3	you want to be flexible, but then there is like overlooking things that
2:18.9	you just don't want to see at the beginning. Yeah, for sure. But if you don't know,
2:23.0	Stephen Chandler, he is the national bestselling author of the relationship roadmap and the author
2:29.1	of Stop Waiting for Permission. And he's the senior pastor of Union church, which is based in Maryland. He has an
2:35.2	audience of over one million people. Yeah, just a really, really powerful leader, really obsessed
2:42.2	with cultures and people and systems and a speaker who just is very passionate about equipping
	...

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