Anthony Simonetti and Stephanie Kelly’s Proposal

Our Story

How We Met
My sister, Nikki, set us up. Her husband, Joe, grew up with and is very good friends with my fiancé’s older brother, Bill. Whenever my sister and Joe would hang out with Bill, my sister always pestered Stephanie about going out with me. Eventually, Stephanie and I began Facebook messaging each other and before we knew it we had our first date set up. Our first date was at the aquarium and I guess I can say the rest is history.

How He Asked
My plan was sort of very short notice. We had a trip planned to visit Boston for a few days before heading to Maine for a friend’s wedding. We left for Boston on a Tuesday and I had received the ring the Friday before. I really wasn’t expecting it to be ready before the trip and was planning on proposing after the trip, however, when I got the ring on Friday I decided I would do it in Boston. We got to Boston on Tuesday, but I didn’t propose until Wednesday night, so for a day and a half I nervously carried the ring around in my pocket. My initial plan was to go to dinner at Top of the Hub atop the Prudential building in Boston and then after dinner go to the observation deck a floor below the restaurant and propose with the lit up Boston skyline in the background. My plan changed slightly when I called the observation deck and found out that they stop taking people at 9:30. We had a 7:45 dinner reservation and I was nervous we wouldn’t make it to the observation deck after dinner, so I decided to go to the observation deck before dinner and propose, then we would go to dinner and celebrate. As soon as we got to the observation deck I was not feeling it at all. It was 7:00 PM and the sun was glaring through the not so clean windows. The carpet was dirty and ugly and the windows had hideous black vents covering half of them at the base that would not be a pretty addition to the engagement picture. So I scraped that idea and decided to do it after dinner at the restaurant. We enjoyed a nice dinner with a great view of Boston. At the end of the meal I asked our waitress to take our picture. Stephanie and I were actually disagreeing over whether or not we should take a picture and that it would be awkward. Our waitress came with the check and I stood up and asked her to take our picture. Stephanie refused to stand up because she thought that sitting would make for a nicer picture. I begged her and she finally stood. We took one picture standing, and then I asked the waitress to take another without the flash and walked over to her as if to show her how to shut the flash off of my iPhone. As I did that I leaned in and whispered to her that I was going to propose. I then went down on one knee and pulled out the ring cam, which I had already had recording in my pocket for a solid three minutes. Stephanie was super surprised and everyone in the restaurant erupted in applause as I asked my best friend to spend the rest of her life with me with a beautiful view of the Boston skyline in the background.