Not every love story starts with a passionate, maybe too passionate, aunt hellbent on playing matchmaker between her niece and the boy who grew up next door, but this one definitely does. After years of "Jessie I know this boy who I think you’d really like” and “Conor you need to meet my niece, I think you two would really hit it off” Jessie and Conor finally agreed to meet in the Fall of 2022. Maybe he was playing it cool, or maybe he was just procrastinating, but Conor waited until Jessie's last day of her holiday visit home to finally text her. They agreed to meet up at Flinders Lane, a local bar in Stamford that Conor frequented for their Spiced Pineapple Margaritas, and one of his go-to first date spots. Little did he know, that this was going to be the last first date he would ever go on. Even though they both came in with reasonably low expectations for a blind date, the night lasted 6 hours, with Conor dropping Jessie off at her parent’s house at 1am. Despite the snail-like pace it took both of them to decide to finally meet, the two have been off to the races ever since.

Now having firmly established themselves as a couple, the new challenge of a 3-hour difference in location consumed their free time. With Conor shipping up to Boston (woah oh oh) on weekends and Jessie splitting time between Stamford and Greenwich when she could come home, the two grew closer and closer. They got to know each other exploring the North End in Boston, a city that was new to Conor, and bouncing between old haunts in Stamford. In February, the ever-scheming Conor realized he now had a person he needed to let in on his plans, so he asked Jessie if she was okay with him signing a 12-month lease in Stamford, hoping to escape the studio apartment he rode out the pandemic in. Jessie, ever reasonable, responded “Of course! Whatever you need to do!” Conor was only somewhat surprised to receive a text the following day declaring, “I think you should move to Boston.” Fast forward to today, Jessie and Conor have built the beginning of a life in the North End, with frequent walks after work along the Boston Harbor, weekend trips in New England and eating more pasta per week than a mafia compound could consume. Their life in Boston felt like an endless honeymoon, culminating in a beautiful late summer evening stroll along the same waterfront route they had taken many times, when Conor got down on one knee and asked Jessie to marry him. She said yes, which is why there is now a website about it. The rest of Jessie and Conor’s story is still being written, and they are so excited to include you in their next chapter.