Our Story

My last first date, the night I met David, was the best date I had ever been on.

And no, not just because I had planned it.

First, he arrived before me and had already found the entrance to our speakeasy; a very good sign in my book and an early indication of the type of person David is (thoughtful, proactive, & I’d later learn, nearsighted like me). From there, the night only got better. David ordered something that came in a very big, very fun Tiki glass and this was another very good sign. He was clearly confident but more importantly, he was playful and ready to have a good time! And boy did we have one.

We excitedly talked about shared interests, bonding over Twitter, music, and our love of animals — dogs in particular. From his Bumble profile, I knew David had a dog, and after 2 rum-based cocktails, I knew meeting her was nonnegotiable. What David didn’t know was that while he was in the bathroom, I asked the waitress to bring us (i.e. HIM) the check — this was a first date after all! She laughed, telling me that she could tell it was a first date but that we looked good together. David offered a third round of drinks before graciously paying. More and more good signs.

Back at David’s PB apartment — with his roommate Jono “coincidentally” out of sight — I met Daisy (David’s 1-year old Pitbull) and we played Mario Kart over beers. Daisy was sweet and so well behaved and David didn’t let me win at MarioKart despite my cheat-tactics and obvious flirting: good sign, good sign, good sign. (Months later, I’d learn David had no idea I had been flirting with him, he was in the zone and not about to surrender a win!).

By the end of our first date, I knew there would be a second and likely a third. I didn’t know where these dates would take us but when I snuck a picture of David asking Daisy to do tricks for me, I do remember thinking “this one’s for the grandkids”.

The Pictures in Question<3

I knew Ashby was “the one” early in our relationship, but I’ll start this story at Thanksgiving 2024. . .

By then, Ashby and I were already on the same page about wanting to get married, what we wanted our timeline to look like, and even what we wanted her engagement ring to look like. Since a lot of the traditional surprise had already been lost, I knew I had to find a new way to surprise her.

While we were visiting Ashby’s family for the holiday and she was conveniently occupied in the kitchen, I started quietly telling her family members that I was planning to propose in 2025 and would need their help keeping it a secret.

As time went on, I realized the perfect surprise would be finding a way to involve both of our families, who at that point had never met, even though I knew it would take some serious logistical planning to pull off. Ashby’s family quickly became my partners in crime, and I was texting and calling them whenever Ashby was out of the house or out of earshot.

After months of planning, and several scrapped ideas along the way, everything was finally locked in. We already had plans to travel to the Bay Area to visit Ashby’s family and meet our newest little niece, Olívia. What Ashby didn’t know was that, as we walked along the beach on our way to brunch before hitting the road, I was about to get down on one knee, with a photographer hiding in the bushes and the whole nine yards.

Ashby was clearly caught off guard, but thrilled at the same time. What she also didn’t know was that when we arrived in the Bay Area the next day, both of our families would be there waiting to surprise her at a very nice lunch she thought was going to be just the two of us. If you haven’t seen the pictures of Ashby’s surprised face, you absolutely need to.

Everyone had a great time, and it was such a special start to our engagement and to the relationship between our two families.