Emily had to take the T into the city to meet Jack. Jack decided to do the same and suggested to meet up at South Station. The whole way there they were texting back and forth, and Jack said that he was going to be late due to maintenance on the T. So, when Emily arrived, she said it was okay, and that she would wait. She waited for an hour. Then Jack finally arrived and apologized for being late. They then went on to have an amazing first date. If you want to see where they all went to check out the Things To Do tab!
Emily was visiting Jack in MA for a few days. It was their last night together for a while and Emily had to return back to WI the next day. They were on their way back to Jack's place for the night, but Jack had to do one thing first. He was playing "You And Me" ~ Lifehouse, and drove them to Magoon Square in Sommerville, MA. (This is where they would always park when meeting each other or catching a fight to WI or MA. Going to Magoon Square meant that they were going to see each other.) Jack pulled over once they arrived and told Emily to get out of the Car. Jack got on one knee, special song playing, tears forming, and asked. Obviously, Emily said yes.