Dating Advice for Women in Their 30s (That Actually Helps) | Modern Dating, Healthy Relationships & Sober Curiosity with Anna Kai

Lo takes a wellness walk with content creator and podcast host Anna Kai through Midtown Manhattan — revisiting the very spot where Anna met her husband.In this episode, Lo and Anna talk love, dating, and what it really takes to build a relationship that lasts. They share personal stories on setting boundaries, sobriety, and how confidence is the true key to romantic (and personal) success — with plenty of laughs and unfiltered wisdom along the way. Key Takeaways:1. Why self-confidence comes before a healthy relationship2. The truth about ghosting, dating apps, and “the chase”3. Sober curiosity and how drinking less changed their lives4. How Anna went viral in her 30s and built a thriving media career6. Real talk on modern relationships, red flags, and trusting your gut Chapters:00:00 – Welcome to Lo On The Go01:10 – Anna’s love story: From dating apps to marriage04:30 – When it’s comfort, not butterflies08:00 – Sober curiosity & the mocktail movement11:30 – Dating while exhausted & the myth of the spark17:00 – Why Midtown still has magic20:00 – Lo’s engagement & dating confidence in your 30s25:00 – Myth or Truth: Ghosting, exes, and the chase36:00 – Anna’s rise to podcast fame & finding your voice40:00 – Final thoughts on love, confidence & showing up Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.