Steve Dean

Online Dating Consultant + Matchmaker

Who is Steve Dean?

Steve Dean is an online dating consultant and matchmaker who's spent the last 4 years living across 12 cities and learning how people create and strengthen both romantic and professional relationships. He currently gives personalized dating advice through his consultancy and matches jobseekers to fun job openings via his "OkCupid for jobs" startup,


More fun facts

  • He matched the CTO of OkCupid to his new fiancé... while he was on a date with her. He actually pulled out his laptop, showed her the CTO's profile, and told her to message him.
  • He's lived rent-free for the last 4 years thanks to asking one question to everyone he meets.
  • He created a Foursquare list of the best wifi/coworking cafes in NYC, SF, LA, Philly, Boston, Seattle, and D.C.
  • He is on over 100 dating sites and apps and has met more than 50 of his closest friends that way.
  • He loves "coworking" first dates -- meet up to work on your personal projects together at a coffee shop, feel like you've both accomplished something great, then go out and chat about your projects over food and a long walk.
  • He writes about dating and feminism, and his favorite dating qualities are empathetic perspective-taking, radical honesty/transparency, and referring compatible friends.
  • He adores snuggling and actually owns a copy of the Cuddle Sutra.


Steve Dean's daily questions for Siren members

What is something interesting about you that almost no one knows?

What do you do to show someone that you care about them?

What's something fascinating you recently learned that everyone would benefit from knowing?

What part of relationships is most challenging for you?

What's the most interesting event happening in the city this month?

Name a neighborhood or park you've been meaning to check out. What made it capture your attention?


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