Stacy and Dylan

Where to Propose in Positano, Italy

How We Met

His side of the story: “Don’t worry about it”, she said with a smile. I was motioning for my tab after finishing a few Budweisers for happy hour. I didn’t recognize the new bartender, but she made quite the first impression. She had tattoos, lip ring, and knew everybody that walked in. Admittedly, I was slightly intimidated. Smoothly I thought to give her just the tip.

I wanted to test my fate again, so the following day I went back to the bar. Once again, happy hour ended bill-free with a smile. Needless to say, I made it a habit to attend happy hour regularly. Not for the free drinks, but the cute smile behind the bar kept me coming back. Luckily, through mutual friends and more Budweisers, we finally got to know each other.

Her side: “Don’t worry about it,” I said trying to hide the stupid smile that was clearly paint on my face.

The boy at the end of the bar was motioning for his tab. I hadn’t seen him in here before.

Fast forward five years…

We had known of each other through mutual high school friends for roughly ten years before we actually started hanging out as friends and eventually dating (at a party in high school, Dyl was the kid lighting 151 rum on fire).

In March of 2013, all of the said mutual friends had ended up back home or were planning on moving back home at the start of the upcoming summer from places they had moved to during or after college… Dylan & I were included in that group of people. I had semi-recently moved back to Connecticut from living in Boston and Dyl from his college years in Springfield, MA.

Before we knew it, summer was in full swing and weekends always looked the same, with the same group of friends meeting at the same bar. Coincidentally, the bar we all frequented, was the same place I worked at. Dylan found his seat at the bar for a happy hour day after day and we always joke that the only reason he really stuck around was that of the free Budweiser’s (will we ever know the truth?).

Five years, almost to the official day of us starting to date later, our life looks a little different than it did when our story first started. Together we have grown as a couple and navigated through life and all it has thrown our way. We have a cute little house in a Connecticut shoreline town that we call home, a sweet puppy (Layla) and out of all the milestones we have hit together, being engaged is the best yet. We are incredibly excited to start this new chapter together!

How They Asked

I always wondered how I would react, what I would say and do when the moment came for Dyl to get down on one knee. Never have we been in any rush to get engaged and we have basically done everything backward as a couple, our whole relationship out of the ordinary. We have shared this life together for the past five years and I have never felt the pressure that comes before getting engaged, with everyone asking “you’ve been together for so long, why hasn’t it happened yet?”, and I know Dylan hasn’t either. Honestly, my response has always been, what’s the rush?

Proposal Ideas Positano, Italy

When we started planning our trip to Italy with his family, a few people made comments about him popping the question while we were away, but the thought never crossed my mind. It was our second day in beautiful Positano, the sun had just gone down and we were all making our move to walk around town to find somewhere to have some wine & a bite to eat. Outside of our hotel, Albergo California, was the most perfect view. So many colors in warm, bright tones, painted on the unique architecture climbing up the endless hills above us. Every sight was lit up by bright lights, there were mountains in the distance and calming sounds of waves crashing against the shore below.

We were posing for a picture, but imagine my surprise when Dyl took his arm out from around my waist, whispered to me “we aren’t actually taking a picture” & got down on one knee. I couldn’t even believe it. Those first words I had thought of for so long came out of my mouth with no filter “are you f*cking kidding me right now?!” Definitely not what I thought I would say, but if you knew me, it wouldn’t surprise you. It all happened so fast, & before I knew it I had literally fallen to my knees. I couldn’t wrap my head around what was happening, it all felt like a dream! It was the absolute most perfect moment of my life & I’ll never forget each and every detail.

Special Thanks

James Allen
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