#2 – I Do, Until I Don’t, with Beauty and Love


I never thought I’d get married. I also never thought I’d live to be thirty. I guess both events caught me off guard. I had had a lot of relationships before this one– like a lot, a lot. I had done a lot of dating and had experienced most things imaginable as far as human bodies are concerned. But this experience, this feeling, was a first.

I should pause here for a moment. I promised you a “tell-all” blog and I do still plan to deliver. That being said, this is one topic where I will hold back, out of love and respect for my ex-wife.  Nonetheless, some personal context is necessary in order to share how my fundamental beliefs about human sexuality shifted and to set the stage for the idea that would become DatePerfect. 

Now back to the torrid romance: For me, the desire to propose was not only rooted in deep love, admiration, and attraction to this beautiful, sexy, smart, and hilarious woman. It was also, for the first time, a basic and primal procreative drive, knowing that we would make amazing children together. I was brimming with a type of optimism I had never before felt. Those feelings led me to love her even more deeply, and I believe she me, and we were off to the races.

It was only years later that I realized I was seeking to marry for other reasons, as well. I was working from a playbook that I had not written, by authors I never necessarily agreed with. Whatever we want to call that invisible force, it’s pervasive, perhaps based in patriarchy, certainly influenced by organized religion, and steered, or at least encouraged, by legislation, taxation, and hypercapitalism. Within my version of it, there seemed little room for variation or self-expression. Whether this was real or self-imposed, I can’t say.

In the end, I found I was trying to fit myself into a paradigm opposed to who I was and what I wanted to be. And, after eight years, we decided to split up. We somehow did this in a supportive and loving manner, an experience contrary to every example of divorce I had ever witnessed. We tried to do it with full consciousness, ironically even more than we’d brought to the table when we got married. In the end, she had often wanted me to be more present in our moments together, while I was looking ahead. Ultimately, had I done both of those things – looked inside and looked ahead – our course would have been much different.

In the post-breakup aftermath, I really started to rethink my ideas about sex and love. What I continue to learn about myself is that I’m a seemingly inexhaustible ‘handful for a partner to manage,’ with a big personality and lot of love to share. As I began to experiment with sexual and emotional relationships, I started to identify more and more with “Other” as my relationship preference. I could no longer pretend that I fit into the dominant paradigm of sexuality, where monogamy and marriage are the end goals. At the same time, I love having deep and meaningful relationships that expand over time into the depths of myself that can’t be reached via casual encounters.

As I began to unpack and process being single, I started to gain some unique perspective. With a clean slate and a new start, I wanted to get back in the dating game, which had begun its dramatic electronic shift. So I started trying to find the best dating sites, or at least the best ones for me. The experience was abstract, overwhelming, unsatisfying, and messy. The experience of IRL dating didn’t seem to translate into a Google search. I wanted to solve the technology problem, not just for myself but for other frustrated daters. And so the idea that became DatePerfect was conceived.   

Click to read the next installment: Single for the First Time in the Digital Age, Sorta

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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: http://dateperfect.com/category/hot-topics/founders-blog


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