Kyle meticulously planned the engagement to surprise Kelly. What better day than his birthday, when they had already planned a nice dinner to celebrate? Kyle's one request for his birthday was walking to his favorite food truck in Boston, Cookie Monstah, for a sweet treat. They had gotten their ice cream and sat at a park bench in Christopher Columbus Park. Kyle's phone kept buzzing, but Kelly just assumed he was a popular guy getting tons of birthday wishes! Unbeknownst to her, it was the photographer telling him she was five minutes away! Kelly suddenly felt a chill sitting in the shade and asked if they could start walking along the harbor. Kyle didn't have a good reason to say no, so they walked....and walked...for another 20 minutes. Finally, Kyle was able to get Kelly to turn around and walk back to the green arches in the park. And that's when he got down on one knee and proposed, catching her by surprise! The best part, Kelly had gone for a scheduled nail appointment the day before without needing subtle prompting from her friends!