Kaaboo 2018, what a time. It was an action-packed music festival weekend with some of our best friends and showcasing some of our favorite artists. It must've been my generational singing voice while fan-girling over Post Malone that originally caught Kayla's eye because we were inseparable for the entire weekend watching concert after concert. Following that weekend there is some debate on exactly what happened but I am 100% positive that Kayla asked me out first. Regardless of who asked who, and the fact that she was obsessed with me, we spent our first date at Civico Restaurant, a beautiful outdoor restaurant in Little Italy (in hindsight this was a classic mistake of setting the bar too high too early but the rest is history!)
After spending months looking at rings and trying to find the one, I finally pulled the trigger and had the perfect ring. I wanted to surprise her but my ship was leaving Maine in a month and she knew I wanted to do it prior to leaving, so time was not on my side. I planned two big trips, one to Newport, RI and another to Acadia National Park, both beautiful and special places to us as a couple that would've been great proposal spots - instead they were serving as my decoys. We had created a "Maine bucket list" which included seeing a lighthouse at sunset and I thought this was the perfect opportunity. I enlisted the help of our good friends Jess and Amber and came up with the perfect plan: we were supposed to meet Amber for dinner but first, we would go to Portland Head Lighthouse to catch the sunset. There waiting for us was Jess (pictured below) with a red-head wig, ballcap, and sunglasses, completely disguised and ready to capture the big moment. I came home from work and of course, Kayla was working late and in the middle of a meeting. I tried texting and calling her but couldn't get her to just leave the meeting. I was racking my brain, texting Jess and trying to figure out how to pull her out of this meeting and to the lighthouse, as once again, time was not on my side. Finally, I texted her "I think this is our last chance to see a Maine lighthouse, I know you're in a meeting but I think we need to leave otherwise we'll leave Maine without seeing one of our bucket list sights here." Unfortunately, all the calls and texts in the middle of her meeting DID make her annoyed at me but the text worked! The plan was back on! We arrived at the lighthouse and the sunset could not have been more beautiful. I gave the strange red-head tourist lady following us way too closely a discreet nod, and then popped the question. I actually don't think I said anything except "Marry me?" and I definitely never heard an answer but figured by her cracking up and screaming that it was a "Yes." We then went out to dinner and popped champagne with all of our friends in Portland (Jess, Amber, and Christian lol). When it rained the next three sunsets, I couldn't believe that everything had fallen into place so perfectly. Last thing I'll say here is let me know if you want to see a picture of Jess in her Eastern European disguise because it's well worth it.