We matched on Hinge. He said, “12”…. [Text shortcut for “Cute smile :)”]

For our first date, we met for coffee at the Tunnel Tops in the Presidio. It was a beautiful sunny day. He had come from a bike ride in Marin… showed up right on time with Winston and perspiration on his forehead and back, wearing a green crewneck, cuffed jeans, and boots.

We sat in the red adirondack chairs overlooking the GG Bridge and the Bay. Winnie waited patiently as we chatted for a few hours about family, work, friends, hobbies, TV shows, our favorite foods, and everything under the sun.

When it was time to go, he walked me to my car, pointed out a “sick matte wrap,” insisted we see Oppenheimer that week, and kissed me on the cheek.

It was love at first sight.

It was the summer of 2023, August 13th to be exact — a day that, unbeknownst to us at the time, would be marked by more than just the usual celebrations like National Prosecco Day, National Filet Mignon Day, and International Left-Handed Day. We had been chatting for a few days on the apps, and after some back-and-forth, I finally gathered the courage to ask for her number. I quickly followed it up with the classic Kyle Special: Hey, Courtney, it’s Kyle from the internet. Smooth, right?

We decided to meet for coffee at the newly opened Tunnel Tops park in the Presidio. And, of course, I had to bring my trusty sidekick, Winston, along — setting the expectation early that I come as a packaged deal. After all, what’s a first date without a little extra charm?

I remember walking up to the café and ordering a latte, while Courtney opted for a black coffee — a decision that would go on to become a little tradition of ours, the perfect reflection of our contrasting yet complementary tastes. We took our drinks over to the red Adirondack chairs overlooking the Golden Gate Bridge. It was a picture-perfect spot, but what really stood out was the conversation. It felt so natural, so effortless — two strangers connecting in a way I hadn’t expected. Every topic we touched on seemed to flow seamlessly, and the conversation felt open, real, and engaging.

After about 15 minutes, I knew I wanted to get to know her more, to spend more time with her. As we wrapped up, I walked her back to her car. And just before she drove off, I made sure to show her how much I liked her by giving her a kiss on the cheek — a small gesture, but one that felt like the perfect way to end what had already been such an unforgettable first meeting.