Samantha and Josh

How We Met

I moved out to Massachusetts from New Jersey the summer after I graduated from college. I didn’t know anyone except for a friend from high school who lived about an hour away who I hadn’t spoken to in 3years. I reached out on a whim, and we connected! He invited me to go out to get some drinks with some of his friends and he and Josh worked together at the same company. My immediate thoughts on Josh were not positive ones! I had too much to drink and certainly could not drive and Josh offered to let me stay over at his place, which was much closer. As a new graduate from college and new to the city, I thought he was trying to take advantage of me and immediately I disliked him even further! I ended up staying at my friends house and harbored a secret dislike of him, even though my friend and Josh were incredibly close. Eventually, after hanging out in groups together, he grew on me slowly. And looking back at that first memory, maybe he was just being a gentleman! Needless to say, approximately 8months after we met, he asked me out on our first date to the MIT Museum, and the rest is history!

How He Asked

On our third anniversary, Josh and I went away to an all inclusive resort in Cancun. We had been living together for two years and we regularly discussed our future lives together, children, dreams, etc. We had even discussed getting married and what our timelines were for that, and we were both on the same page. We had this amazingly beautiful vacation planned. One night he asked me to go down to the beach to star gaze with him, something we would regularly do together. We stared up at the stars while lying on the sand, and then we went back inside. Needless to say, I was surprised he didn’t propose! But I enjoyed the moment.

After we returned from our vacation, Josh planned this amazingly romantic date night or going to the orchestra and then going star gazing again. Star gazing we both love, but going to the orchestra is something that is more of a me thing to do. He insists I get dressed up, which is very out of the ordinary for him, and we have an amazing evening. Once again, we go out star gazing in one of our usual spots, lying on the rocks and looking up, and then we head back to the car.

A week or so later, he plans another romantic dinner. At this point, I was trying to have 0 expectations and just enjoy the moments. We get a fancy bottle of wine, which is unlike us. We usually get the second cheapest option or the house wine, appetizers, full entrees, decadent desserts. And then we head back home.

Two weeks or so later, we attended a friend of mine’s wedding. We danced all night together, drank and laughed. I even told him that I had thought he was going to propose at our orchestra date and he laughed.

A week or so after that we took a trip out to Nantucket Island, somewhere neither of us had been. It was a surprise date, which was not uncommon for us. We both love planning surprises for the other! He told me, in reference to what I said at the wedding, to not expect anything big on this trip! The trip was the surprise! I laughed and said “yes! I know!” We stayed at a beautiful bed and breakfast and then around sunset trekked off to the beach to watch the sunset and to star gaze. Again, he reminded me that all the surprises were done! While we were out on the beach, just as the sun set and it was dark, he got up and told me he was going to go pee. So romantic, right? He comes back over to where I was sitting in the sand with a little treasure box that looked similar to the treasure boxes from Zelda, a game we both love. He opened up the box and inside was a smaller ring box surrounded by large fake glowing diamonds to light up the box. He opened up the ring box and inside was a beautiful ring!

He asked me right then and there and then told me that he had had the ring box in his pocket on almost all of the previous romantic dates that I had thought he was going to propose to me at, but he wanted it to be a true surprise so he had “fake proposal dates” to throw me off, knowing full well I would have had it in the back of my head it was a possibility!

Samantha's Proposal in Nantucket, MA

Proposal Ideas Nantucket, MA