Kyle might say that he and Jess met for the first time at a party at "The Den" – Kyle's college apartment – where Jess initiated their first kiss. However, the first time they formally met was during a beach trip with mutual friends the summer before Kyle's senior year. After a couple months of movie nights, parties, and a text message prank about flying to Vegas, Jess made the first move at the fated Den party. Jess and Kyle spent a lot of time together after that and officially decided to call their dating anniversary January 16th, 2012.

You'd think after seven years of dating I'd have thought of a plan for "the day" sooner than I did. Turns out, despite being risk-averse and a proponent of pre-planning events (to the point of being annoying - ask Jess), I can be indecisive and non-committal when I otherwise shouldn't be. Thankfully, with a bit of guidance from my parents and reflection on meaningful experiences Jess and I had over the years, it was easy to nail down "the plan". Rewind to Summer 2013 when we were living at my parent's house saving money for an apartment. One motorcycle's worth of "apartment savings" later, we found ourselves frequently riding two-up on short-distance trips to friends' apartments and local food/beer stops. Wanting to attempt something more adventurous, we committed to a ride to Beavertail Lighthouse in Jamestown, RI. After I (unsurprisingly) ended up getting us lost twice, we arrived at the lighthouse and improvised an afternoon walking through Jamestown center visiting local shops. All-in-all, the day ended up being one of our favorite dates. Fast forward to 2019. Struggling to decide on "the place", I recalled our trip to the lighthouse and how well it represents everything I enjoy about our relationship and sharing a life with Jess. With the location picked and dinner reservations in place, all that was left was to hope for good riding weather. Thankfully, the day turned out to be one of the best riding-weather days of the season. Despite a minor scheduling hiccup, a shakier-than-I-thought cover-up story, and many conversational landmines dodged by feigning ignorance about how we "seem to be heading the same way as the lighthouse trip years ago", we made it to "the spot" with Jess only suspecting something was up as we pulled into the parking lot. One garbled speech later -to my credit I hit all the major points- Jess said "Yes"! We spent the evening enjoying dinner at a dockside restaurant in Newport in view of a perfectly-timed (read: planned) sunset.