Chloe Shih breaks down all the best dating tips she wishes she knew in her 20s. Learn how to flirt, which guys to date, and how to build a relationship that lasts.

Chloe Shih is a creator, entrepreneur, and former tech operator who shares an honest look at modern ambition, relationships, and personal growth. She reflects on love, therapy, career pressure, and how the right partnership can reshape the way you think about success.

Chapters

00:00 - Intro

00:34 - What makes a relationship actually work

03:32 - The biggest lesson from couples counseling

03:55 - The “four horsemen” that predict relationship failure

06:33 - Chloe’s advice on flirting and seduction

07:22 - How she met Kevin

08:39 - The disastrous first date

11:43 - How Kevin won her over after rejection

15:37 - The Facebook prom turning point

16:43 - The 25-item partner checklist

17:22 - What was actually on Chloe’s list

18:36 - Why you should not date the person who only looks good on paper

20:09 - How a happy relationship changes your career

20:30 - Redefining ambition and “the bag”

21:45 - Success without scarcity

22:20 - Good mindset trick

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About The Burnouts

The Burnouts brings you raw, unfiltered conversations with today’s top founders, creators, athletes, and culture-shaping entrepreneurs. Hosted by Stanford roommates turned startup co-founders Phoebe Gates and Sophia Kianni, the show goes beyond the headlines to reveal the real stories behind ambitious careers.

Past guests include Paris Hilton, Chelsea Handler, Kris Jenner, Karlie Kloss, and more. Subscribe for the insider playbook to build your dream career.

Dating 101 as an Ambitious Woman: How to Seduce Anyone (ft. Chloe Shih)

The Burnouts with Phoebe & Sophia

Dating 101 as an Ambitious Woman: How to Seduce Anyone (ft. Chloe Shih)