160. Break The Dating Rules and Be Your Own Matchmaker with Oz Chen

Playing the Game of Love with Joy, Community and $5000

Our Valentine’s Day episode is for the single people and their busybody friends. We met our guest, Oz Chen at CampFI last month and were immediately impressed with his high agency in regards to his dating life. Oz decided to approach dating differently wanting to make sure he kept it fun and avoided getting jaded during the process.

Oz Could Be Your Valentine

I’ve personally felt the up and downs of swiping on the dating apps. You can see on the apps that people are tired of this process too. In a world of lazy cliches and “swipe left if you have a fish in your profile”, Oz Chen decided to take a different approach. He started his own “matchmaking program.”

After investigating different ways to invest in his dating life, he realized that people were paying upwards of $10,000 for matchmakers. This plus an AI tool charging $100,000 for matches made him reconsider how much he’s investing in his dating life. Oz decided to use what he already had to his advantage: a great network.

Oz invited his friends, and now the internet, to participate in his matchmaking program. If he finds a life partner, he’ll pay out a referral fee to the person who connected them. This encouraged his friends to pull out their phones immediately and see who they knew who could be a good match. This also prompted them to ask him what he’s looking for. So Oz created a Date-Me Doc, a trendy low tech phenomenon in our niche corner of the internet. People are creating Google Docs or Notion pages that highlight what they’re looking for and can provide more color on their own personalities.

Sammie and I had so much fun chatting with Oz Chen! We spent a lot of time giggling about dating and had multiple unlocks during the conversation around how to be a better and happier dater. I’ll be applying Oz’s dating mental model and balling out on my next few Hinge dates.

Have you tried an unconventional way of dating? Do you have a Date Me Doc? Let us know! If you’re in a relationship, tell us how you met your partner, it may spark some inspiration.

Takeaways From This Interview:

1. Don’t date jaded. Take a break if you’re finding yourself in a dating rut or no longer finding dating fun. If you’re being sassy in your dating prompts, it’s time for a break.

2. Find creative ways to make dating a joy instead of a stressor. In Oz’s case, he got his friends involved in his dating journey and encouraged them to set him up with good matches and play this game of love with him.

3. $100 vs $100,000 investment approach. How much are you investing in the things you value? We often spend more time and effort deciding on a new dehumidifier (it’s great btw) than finding our life partner. You don’t have to spend $100,000, but are there ways you could be investing more!

Find More on Oz Chen:

• Ozchen.com

• Oz Chen’s Newsletter

• Oz's Matchmaker Program

• Oz’s Date-Me Doc

Make your own Docs with Oz’s Templates:

Date me doc template

Matchmaker program template

Show Notes:

• Michelle’s Essay: Rearranged Marriage

  Rearranged Marriage

• Earn & Invest Interview:

• Date Me Doc Directory: https://dateme.directory/

• Tim Ferriss

If you make a Date Me Doc, share it with us and we will share it in our next newsletter!