Online Dating for the Midlife Ugly Duckling

If you’re looking for a partner, don’t search for a match.

Coming out of fourteen years of being together and four years of mourning, I didn’t recognize the dating landscape. And who would have ever imagined? The way we did such primal things like meeting and connecting with one another– would change. It might be that the years between 1997 and 2015 were radical years of accelerated change, but still.

I didn’t know how to date online. I wasn’t particularly good at it in person in 1997.

This time, I wanted something different from the picturebook marriage. We’d had the Memphis-style architect house and typical markers of a comfortable life. Instagram-worthy holidays. I had beautiful photos with my baby in the lavender fields in Sénanque Abbey. But between pictures? I couldn’t totally relax when the man who was taking the photos was home.

Photo: Mika Baumeister

 

Machine Learning

I thought I knew what I wanted in a partner. It turns out, my mind was playing tricks on me. It often did. I’d fall in love over and over again with the same guy: they’d walk into my life in a different body, different age, and from different cities around the world. They were one and the same, just like the heartbreaks I’d experienced with each one of them.

Basically, I wasn’t dating any of these men. I dated a type. When my best girlfriend pointed out, “Types. Look where that’s gotten you,”  my eyes widened. I stopped breathing for a second. Types. They kept me mired in what I thought I wanted in a relationship.

Later that week, I told my best guy friend about my tendency to date a type. He shot right back and asked me three qualities I look for in a man. 

I thought for a second. 

• Curiosity: He’s curious about life, and he piques my curiosity

• Humor: He makes me laugh

• Charge: Takes charge of his curiosity and his life. 

I stared at my screen, app open, my face lit by its blue light. I was paralyzed. The combinations of preferences and what I wanted in a match made me dizzy. That and swiping on the result of preferences and location at a specific time on a particular day: what would it give me in the end? Flavor of the month? Or maybe a confirmation that forty-something is just plain old. 

Thank god for my best guy friend. He had a look at my phone. We uploaded photos, played with settings. I kept swiping left to skip profiles. I didn’t want to know what actually happens on apps. A girlfriend gave me an oddly compelling reason to swipe right and say yes to a profile: help the machine learn what I’m looking for. I swiped right. I matched. I moved into chat. I didn’t know what I was doing, but it turns out I didn’t need to know. I had game.

When in Doubt, Keep Swiping

After some practice on the app, I moved away from type and started noticing things. I saw regional differences. In the Bay Area, more men were fluent in yoga and meditation than I expected. Men in the Tri-State area seemed more cynical than those in other places. The older man between coasts seemed resigned. When I landed in Tokyo after two weeks of swiping in the US, I was shocked. I’d moved into what felt like a grandpa section of the app.

And that was okay. This was an experiment. As experiments do, they taught me things. I learned I’m done with babies: having them and raising them. I’m most likely done with marriage and cohabitation. I thrive on solitude. I admire men who take care of themselves. I don’t believe in completing each other. 

I caught myself. Do I even want to be in a relationship?

I did. I was ready. And scared shitless. If in my twenties I wasn’t exactly desirable, I would have to be completely invisible in my forties. Invisibility definitely seemed the worse of the two. I had a sinking feeling about it being confirmed.

I swiped through the fear of invisibility. I kept swiping because it was the only way to find out.

Defining and Refining: Not Only the Relationship

Swiping left and right, I thought I was learning how to date online. I thought I was letting myself be seen by people who landed where I’d cast my net. I was wrong. I was actually learning how to exist online. And I was learning to let myself be seen: by me. 

I was getting to know myself. Who had I become over the last fifteen years? I was quickly learning to make room for myself. What do I want my life to look like? 

It came in handy whenever I was asked the “What are you looking for?” question. I’d describe recent daydreams about my ideal life, instead of offering one of the standard multiple-choice answers: Hookup / Casual Relationship / Something More Serious / Not Sure.

This approach suited me. I wasn’t looking for a hookup. Nor was I looking to integrate someone into my family, or for them to integrate me into theirs. The world didn’t seem ready for that kind of neither-here-nor-there. If I found him intrigued and curious about how my life was changing, we’d meet. 

And I kept swiping. 

With each swipe, I learned about the life I was giving myself permission to know. Each time I noticed something new about the process or me, I made adjustments to the app: a photo, my blurb, the age settings.

Photo Editing

I stopped choosing the “hotter” photos of myself to upload. Instead, I started choosing me: who I am now, and who I’m becoming. I chose photos of me doing the things I loved, instead of the ones I imagined would attract my type. I chose photos of me in places I wanted to go back to, maybe live in one day, instead of the places he might frequent. I chose photos where I might not be the most flattering, but the ones where the qualities I wanted to expand and nurture were obvious.

Once these calibrations became a regular habit, I noticed a shift. I drifted away from my type, as if being carried by a current. What if I can’t get back?!  I panicked until I remembered I didn’t want what I had before. I let my swiping carry me. I let choosing myself carry me onward. 

In these new waters, I noticed conversations were deep and at the same time, safe. The less I censored my curiosity the more I was met with wider eyes and heartier laughs. Then, after rubbing his chin and scruff, my match would offer a whole lot of truth. When the experiment was “what happens when you push weird, authentic me to the max,” getting to know someone who braved matching with me became first moments of a real connection.

Location Settings and Finding Each Other

I learned I’m here. Here is defined by me, where I am. I’ve learned to trust whoever he is, he will find me as long as I’m deep in the longing, not of the ideal man, or him, even. But in the longing for my calling. For my path. For where I feel most peaceful. Where my life unfolds by its own laws of nature.  

If you’re looking for a partner, don’t search. Instead, go deeper into what gives you joy. 

Be in the places that excite you, whether tactile and physical coordinates on the Earth, or online and digital spaces.

Be in your integrity when you show up in these places. Use language, both verbal and nonverbal, that makes you you.

If you’re looking for an ideal partner, go ahead, set up an online profile. But instead of swiping for an ideal partner, swipe on you. What gives you joy? 

Date yourself. Choose the life you envision for yourself. Get to know what it looks and feels like to choose you. Let go of the parts of you you’ve outgrown. Keep choosing yourself, at each turn and notice who you are and how you’re showing up.

Get to know yourself and who you are today. Your match is a mirror of your joy and the possibility of your life unfolding. 

The rest- where you will live, how you spend your day, all that inspires you, you in your highest form. All this, and the person to witness you in the flow of your life- will follow.

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