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  • DATEWORKING

    wisdom and wayfinding through the modern dating ecosystem

  • Hi, I'm Steve Dean — 

    your personal dating consultant

    Together, we'll completely reimagine your dating life.

    • We'll assess your personality and preferences.
    • We'll talk through your fears, concerns, and patterns.
    • We'll reflect on who you might be most compatible with.
    • I'll take you on a tour of the dating app landscape.
    • We'll gather any photos and set up any profiles you need.
    • We'll practice your intros and how you build rapport over time.
    • We'll discuss your ideal date ideas.
    • We'll evaluate your dates and determine ideal followups.
    • We'll design the best relationship possible for you and your partner(s).

    Let's lay the foundations for the next decades of your life.

    I'm happy to offer single sessions as well as multi-month support.

    Book a free call with me
  • What to Expect During Our First Free Coaching Call

    1. Diagnostics

    We'll dive into your current life, exploring your dating history,

    habits, commitments, frustrations, and challenges.

    2. Strategy + Goal Setting

    We'll discuss where you'd like to see yourself in the coming months and years,

    and what action steps you're prepared to take in order to make that a reality.

    3. Realtalk + Referrals

    I'll share my vision for how we might (or might not) work together, then tip you off to any

    events, communities, or professionals that I think you'd benefit from exploring.

    schedule free call now
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    My story...

    I started Dateworking in 2011 because I began to notice that our social, romantic, and professional lives were all becoming more intersectional than ever. Whether we're transitioning to new cities, new communities, new jobs, or new romances, we rely on many of the same values, apps, and tactics to guide us.

    I strive to explore, share, and create connection in all its live-affirming forms: finding new friends and communities; meeting new business partners and startup mentors; exploring our relationship with ourselves, and finding love, intimacy, and romantic partnership no matter where we find ourselves in life.

    Today, as a dating and relationship coach, I love working with individuals who want to make meaningful inroads across all the different spheres of relationships in their lives. Schedule a diagnostics & strategy call with me anytime!

    Since 2011, I have advised, recruited, and consulted for dozens of dating companies, including OkCupid, CoffeeMeetsBagel, Hinge, Spectra, and Happy Hour. On the business side, I like to focus on competitive research, business development, user acquisition, team expansion, and my personal favorite: product/launch strategy. I want to see a world with dating apps we're proud to put on our home screen.

  • Dating & Relationship Library + Newsletter

    For over 25 years, I’ve been a relationship nerd, obsessively trying to learn all that I can about how we find, form, and sustain relationships.

    I'm currently building up a living knowledge base of dating & relationship best practices, events, platforms, professionals, venues, books, games, questions, and philosophies that lead us to heightened self-awareness, social & technological dexterity, and the ability to generate sustainable and empowering connections anywhere we find ourselves in life.

  • Steve in the news...

    Washington Post Opinion Comic featuring Steve Dean
    hiiii
  • Thousands of people come to me each year for insights about the future of dating, relationships, careers, and personal development.

     

    Want to join them?

  • Steve Dean, Host, Dateworking Podcast

    Dateworking Podcast

    This is a podcast about all the relationships of our lives, and the purpose-fueled actions we can take right now to lay the groundwork for antifragile future relationships we'll be proud of.

    Join me in exploring the principles, habits, and communities that make relationships meaningful, sexy, grounding, and transformative.

    LISTEN
  • Follow me on Instagram for dating & relationship tips, insights, and interviews with the founders of your favorite dating apps!

    Follow @DateworkingHQ

  • Connect with me anywhere

    Substack

    Substack

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    Threads

     

    LinkedIn

    LinkedIn

    Instagram

    Instagram

    Email

    Email

     

    Facebook

    Facebook

    Medium

    Medium

    Twitter

    Twitter

    Quora

    Quora

    Patreon

    Patreon

  • Check out my latest quotes and interviews

    People are using LinkedIn as a dating app

    What your psychologist wants you to know about your dating apps

    The 6 Top Tinder Tips Recommended By Professional Dating Coaches

    True Love Is Waiting For You On Uber & Yelp

    Dating apps turn finding love into a video game — and lots of people lose

  • Considering a personal consultation?

    Answer a few questions in the 5-minute survey below in order to learn about yourself and to set us up for a successful session together.

     

    At the end of the survey you'll find links to insightful personality quizzes.

    START SURVEY

Copyright 2026 Dateworking

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