3. Single for the First Time in the Digital Age, Sorta

Jonathan DeLong By Jonathan DeLong  - March 5, 2018
3. Single for the First Time in the Digital Age, Sorta

Suddenly I was single, having moved back to San Francisco from Santa Barbara. I’d only tried online dating once before getting married, so I decided to explore the digital dating landscape further. I wasn’t really sure where to start, so I figured researching the top dating providers would help me make the best decision about which provider to sign up with. If I wanted to find the right person, first I had to find the right online dating community.

Overwhelm with Online Dating Sites

So I started to research: It was like drinking from a fire hose. The deeper I dove, the more online dating sites I found. There were literally hundreds— websites, mobile apps, meet-ups, matchmakers, dating coaches, and so much more. While I was overwhelmed by all the options for dating sites in a “lizard brain” kind of way, I was actually even more overwhelmed by all the people, in a kid-in-a-candy-store kind of way. Both kid-in-a-candy-store good and bad.  I was excited and nervous. Like, “omg… look at all this candy, how exciting?” and at the same time,  “look at all this candy! What’s the catch? Am I being scammed?” Then there was the socially- and self-imposed guilt voice, “Should I even be here at all?” It was paralyzing.

The whole experience was disorienting and for a few reasons. I had always been a decisive person, accustomed to making clear, fast decisions. Sometimes this has been an asset and other times a disadvantage. I had never really been shy about dating and had been, in general, unflinchingly fearless when it came to rejection. I was always willing to be playful and flirty— again, for better or worse.

DigitalCondom for Online Dating Protection

These feelings and experiences led me to start a company called DigitalCondom, whose mission was basic identity verification and violent-crime background checks ahead of an online date where strangers were meeting for the first time. The first goal was to solve the kid-in-a-candy-store dilemma.  We wanted to protect people in the online dating space by programmatically narrowing the number of safe, and therefore viable, contenders on any given dating site.  So I formed a company with a friend and did some branding, filed trademarks, and got all the domains and social sites secured. Things were moving along. We were talking to potential users, testing business models, engaged in soft-chats with venture capital, when a potential new feature set derailed everything. Then I lost my co-founder to her dream job, running social and digital media at Playboy. I certainly could not be upset with her for pursuing that, but it did leave me rethinking how to proceed.

I found myself at yet another crossroads. As part of the DigitalCondom offering, we had envisioned a comprehensive list that people could use to find, sort, and compare all the dating sites. In speaking with potential investors and users, it became apparent that this would need to be a service of its own, which left us with a hard decision to make. While DigitalCondom was a fee-based consumer service model designed to fit for tens of thousands of users, this new project would be a free consumer service, which means it would need a different revenue source, and we were planning to orient it for millions of users. As such DatingPerfect was born and DigitalCondom got laid… to rest…

Decisions, Decisions…

This was not an unfamiliar theme for me: choosing between two or three or four choices that seemed equally desirable. What I didn’t know at the time is that this difficult decision was just the beginning. The choices would get harder, life, in general, would get harder, and soon dating would be the last thing on my mind. In fact, I think it would be fair to say that DatingPerfect became to me what perhaps a post-breakup Tinder membership is to many: something comforting and exciting to hold on to during an otherwise dark time. Like people who use Tinder for swiping-entertainment only and never actually meet up with anyone.

As I have shared thus far, I came back to San Francisco from Santa Barbara after an amicable and loving divorce and thereafter started DatingPerfect. What I haven’t yet shared is that this was never my plan. Far from it.  In fact, I had planned to take a cliche post-divorce vacation to South America to “reset my compass” before starting anew in the emotional, geographic, and professional sectors of my life. I even thought of permanently resettling down there. I had my itinerary and travel vaccinations, had divested most of my belongings, and I was ready to go.

However, shortly before leaving, I got a life-changing call informing me that my mom in San Francisco had been diagnosed with stage 4 lung cancer. So, instead of this grand adventure seeking lightness, I headed North to help and settled into what would become the most challenging 11 months of my life; and as you will learn that’s saying a lot. While this ties deeply into the founding of DatingPerfect, at this point I am not ready to share more on this topic, but I promise I will in posts to come.


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Jonathan DeLong
Jonathan DeLong
Jonathan DeLong is hooked on tech, and has been working with startups and entrepreneurs for the last decade. With experience building global cross-functional teams for enterprise and infrastructure providers, to seeing garage-based startups from their ‘fast-pitches’ thru launch, he truly believes anything is possible. Often giving his time freely to both emerging entrepreneurs and philanthropy, Jonathan’s heart is as big as they come. When not deep in strategy and API based business models, you will find him swimming, on a road bike, or simply traveling globally. A San Francisco native and a graduate of the University of California in Santa Barbara, Jonathan currently lives on a sailboat in Oakland, California. Learn more on Jonathan's founder's blog: https://datingperfect.net/category/hot-topics/founders-blog
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