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 relationship

2. The truth about ghosting, dating apps, and “the chase”

3. Sober curiosity and how drinking less changed their lives

4. How Anna went viral in her 30s and built a thriving media career

6. Real talk on modern relationships, red flags, and trusting your gut

Chapters:

00:00 – Welcome to Lo On The Go

01:10 – Anna’s love story: From dating apps to marriage

04:30 – When it’s comfort, not butterflies

08:00 – Sober curiosity & the mocktail movement

11:30 – Dating while exhausted & the myth of the spark

17:00 – Why Midtown still has magic

20:00 – Lo’s engagement & dating confidence in your 30s

25:00 – Myth or Truth: Ghosting, exes, and the chase

36:00 – Anna’s rise to podcast fame & finding your voice

40:00 – Final thoughts on love, confidence & showing up