lmost every couple has the highlight reel (we should talk if that’s not the case): the first date, the first kiss, the first trip, meeting friends and family, the proposal, the wedding. Those are the milestones people ask about, and they matter. But when I think about how Alex and I got here, the milestones simply enhance everything we share in between — that’s where life and living really happen.
From the beginning, things moved fast. We matched on Hinge in August 2025. Our wedding is in February 2027. And I’ll never forget how she matched with me. My Hinge profile listed three options for someone to pick what our first date would be, and it was something along the lines of “walk on the river,” “coffee date,” or “I make you a cocktail.” Her first message to me was “I’ll try the dangerous one haha.” It stood out as playful and intriguing. To my relief, she followed that with, “but we should probably make the cocktail our second date.” I think we both had some healthy reservations about a first date being at my place.
One of the other things I noticed from her profile was that she loves pistachio ice cream. So I proposed an ice cream tour of West Loop Chicago for our first date. We would meet at Jeni’s Splendid Ice Creams and then wander to a couple other places to see who had the best pistachio ice cream.
What ended up happening was a bit different but still memorable and awesome. I remember sitting in the parlor waiting for Alex when she came bursting through the door with a big smile. It was raining outside and she had hurried over from work, which was a solid 20-minute walk. She apologized but let me know she needed to run to the restroom before we ordered. It turns out that as she was closing her umbrella it cut her finger and she had started bleeding. She patched herself up with a paper towel and we stayed at Jeni’s for over an hour getting to know each other. Looking back, I can see how we both approached that first meeting with vulnerability, humor, and curiosity — all of which are heightened (in the best way) by being present.
Unbeknownst to Alex, I had also made a reservation for proper dinner just in case things went well. So I was thrilled when she asked if I was hungry. And it felt like a smooth move to casually mention that I already had a table waiting for us. We closed the place down and agreed that we definitely wanted a second date. Maybe that cocktail would happen after all…
There’s more to the story that I’ll keep sharing in each entry. I didn’t know it at the time, but this is where my groom season started. And it’s influenced how much of our relationship — and my decision-making — has developed since those first intimate moments over ice cream.
Before and after
Before
The match
Before I decided to try Hinge, I had experienced some significant ups and downs — especially in my love life. Although I had been separated from my now ex-wife since September 2023, my divorce wasn’t finalized until January 2025. I met someone in February 2025 but we never defined what it was we were doing. It was on again off again for a handful of months before I literally walked away from what felt like a dark rollercoaster ride of anxious avoidance and entitlement. I booked a trip to The Body Holiday in St. Lucia to reset and recenter. Not long after I got back, I decided to try Hinge as a way to connect with women while being able to be precise and transparent about what I wanted, which was to get to know people in an intentional way before jumping into something physical and/or undefined. I was open to (and hoping for) a long-term relationship but I also wanted to explore personality types, attraction, and overall compatibility before starting a committed relationship on little more than a whim.
In typical Type A fashion, I calculated how many people’s profiles I would need to read to even begin to develop a representative sample set of potential partners in Chicago. I don’t remember what the number was, but I swiped through thousands of profiles within a week or so. While that volume felt crazy, I was hyper-selective in terms of who I chose to match with. Overall, I ended up meeting three people in person. Alex was the second of the three. And she showed up in a way that created a dynamic pull that I was genuinely interested in exploring to the exclusion of others.
After
The first date
I walked into Jeni’s planning an ice cream tour and walked out of a restaurant we’d closed down, knowing I wanted to see her again. In the scheme of things, having a great first date is not necessarily rare. I don’t want to oversell it. Equally, I got to experience a glimpse of Alex’s passion for life, spark, and depth that felt rare. I trusted my gut on that — and I’m glad I did. That first date with Alex brought more brightness into my life, which was refreshing because I was admittedly skeptical of how my little Hinge experiment would go. One of the things that helped me stay present with Alex moving forward was to keep notes from our conversations. It helped me remember her story and preferences. And it provided a ton of context for planning future dates with real intention.
“The milestones simply enhance everything we share in between — that’s where life and living really happen.”