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.
