Chris planned out the details of their proposal while he was working out of New York City in the spring of 2014. With Alison’s birthday weekend approaching in early May, Chris felt it would be the ideal time to pop the question but he wanted the opportunity to be right. To start the weekend off with a nice surprise, Chris planned for Alison’s brother to fly into town and surprise her on Friday morning. Dinner reservations were made for Saturday night to celebrate in Boston’s Seaport district, but they ended up “stopping” for a drink at a nearby restaurant, where Alison was met by some friends for a Surprise 30th Birthday party. What at this point had become an incredible weekend full of surprises was soon to become even more exciting.
The real surprise was on Sunday, May 4th, when Chris, Alison and Tommy headed to Fenway Park for an afternoon Sox game. Chris requested their Uber drop them one block ahead of Alison’s old apartment in Kenmore Square. Tommy felt an “urge” to use the restroom next door, all planned by Chris, and on Alison’s former apartment stoop where Chris and Alison had spent many nights hanging out and chatting, Chris got down on one knee and popped the question. Tommy snuck out of UBurger just in time to snap pictures, and after enjoying a celebratory Fenway sausage on Lansdowne Street, the newly engaged couple took in a Red Sox Sunday matinee.