Steve Dean's Dating Library

cultivating connection, curating collections, and leaving things better than we found them

My dear friends! My fellow dating nerds, relationship builders, and seekers of practical wisdom! I have finally come up for air.

I’ve spent 13 unlucky years deep underground in the seedy underbelly of the dating industry, listening in as founders talk about what they’re building next, and CEOs talk about how to colonize more user attention. I’ve subjected myself to a relentless barrage of the horrors of our modern digital existences: messages from humans, bots, and AI thots across over 300 dating apps; 200-400 push notifications per day; and ads about dating, flirting, and AI girlfriends so absurd that I felt compelled to document them.

But — I’ve also been talking to singles, couples, throuples, and beyond, nearly every day, learning their insights, and mapping out strategies for how they can find what they desire most amidst a vast ocean of distraction and muckety muck.

One thing is certain: digital dating of the 2020s is on a maddening downward spiral toward superficiality, where modern apps’ only goal is to get us hooked on the dopamine drip of an endless supply of cuties at our fingertips. All sugar, no substance.

Looking ahead in 2024, I have one key takeaway: if we actually want to meet people we’ll genuinely get along with, the most important thing we can do for our online dating lives is to infuse our whole self into every section of our profiles, so that anyone encountering us can meaningfully assess compatibility.

This means that every prompt, every photo, every caption, every voice and video snippet, needs to do some heavy lifting. Most dating apps today are asleep at the wheel. Remember, every relevant compatibility metric that we fail to include upfront means that either a) someone won’t feel confident enough that we’re a good fit, and will skip right over us, or b) we’ll be stuck trying to exasperatedly suss out compatibility downstream — in our messages and on our dates — precisely when it’s the most tedious, frustrating, and costly.

There’s no excuse for why in 2024, at the cusp of humanity’s AI revolution, we should be only finding out that someone doesn’t want kids after we’re face to face with them on a date. No excuse. This should have been table stakes for any app worth its snuff.

Modern apps have mostly failed us, and we need to do more of the heavy lifting ourselves if we are to retain our sanity. I know that it’s hard to translate all the dimensions of our lives into a dating profile, especially when the likes of Tinder, Hinge, and Bumble give us so precious little real estate to work with.

In 2020, I actually transitioned my work from consulting for dating apps, to coaching individual daters, because that’s where the core challenges lie right now, at least until the AI revolution either fixes everything, or renders everything unfixable.

But I’m just one person, and there are only so many people I can coach at a time.

Until now.

Last year, I decided to start building a cohort-based seminar series that captures all the key components of my coaching practice and converts them into step by step lessons that lead to far more compatible matches and far more meaningful dates.

Here’s what I’ve optimized the course to deliver:

• fluency in talking about our needs, desires, and relationship goals

• the skill to craft profiles that serve as love letters to our ideal people

• compatible matches whose profiles don’t make us feel mindnumbingly bored

• playful ease in messaging, without sacrificing expedience

• juicy, memorable dates worth savoring for years to come

• active feedback on our photos, profiles, messages, and demeanor from our group seminar cohort

I’m still coaching each day, but starting March 4th, I’ll be kicking off the first live cohort of this course. It will be limited to 10 people, and we’ll meet for 8 weeks. We’ll have weekly discussions, hold each other accountable, and breathe a bit of camaraderie and hope back into the process.

So what now?

I want to talk to you!

I’ve been heads down working on this course for most of 2023, so I’m aching to hear the voices and the perspectives of every person on my radar, regardless of whether you’ve already gotten yourself into an awesome relationship. After all, if you’ve successfully found your main squeeze (or even a series of side squeezes), I want to celebrate with you, and unearth your hard-earned wisdom! Maybe one day we can even turn your own findings into a fun collection in the dating library!

Let’s talk.

Schedule a call with me here.

I can’t wait to hear from you.
~ Steve

PS — If you happen to be in NYC and want to hang out IRL, I’ve been hosting free monthly Saturday city walks where we spend 12 hours wandering waterfronts and neighborhoods, immersed in conversation. Come meet my friends, enjoy fresh air, and delve into deep talks about allllll of the things!

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