Allie and Jacob met as many couples do these days, by swiping right on the dating app JSwipe. After a few days of chatting, they went on their first date at Harvard Gardens in Beacon Hill on July 9, 2017, and the rest was history. The first date turned into a second date, which turned into a third date, and so on, eating and drinking their way through Boston and Somerville and beyond.

On October 9, 2021, Jacob planned a day full of their favorite fall activities in their beloved neighborhood of Beacon Hill, and even 'incepted' some of the ideas into Allie's head so the itinerary didn't seem too planned out. They started by having brunch at one of their favorite brunch spots, Harvard Gardens, where they went on their first date. Next they walked over to Boston Public Market and grabbed some apple cider donuts and apple cider from Red Apple Farm. Then looped back their apartment in Beacon Hill and made apple cider and whiskey cocktails and brought the cocktails, donuts, and a picnic blanket to the Charles River Esplanade. To Allie's surprise, they 'coincidentally' ran into an Instagram-famous Norwich Terrier on the Esplanade! After they wrapped up their picnic on the Esplanade, they walked back to their apartment where they made another cocktail to drink on their beautiful roof. When they got up to the roof, Jacob had the idea to prop up Allie's phone a take a picture with self timer. Meanwhile, Jacob's phone was playing a playlist with their favorite songs. As Allie was getting ready to pose for a picture, Jacob surprised her and got down on one knee! After Allie said the easiest 'Yes' of her life, they celebrated with more of their favorite things that evening: dinner at Contessa, a Jared Freid comedy show, and an overnight stay at The Newbury Hotel.