Roxie Rodriguez was just your average 20 year old college graduate, trying to accomplish her life long dream of becoming an author. She had a steady job, a group of friends who supported her endeavors and an unexpected friendship with someone named Fifth Avenue Boy. Its not until some time in the summer; Roxie makes a rash decision to make a 3 month trip to London, England to hopefully find a publisher and to possibly secretly meet Fifth Avenue Boy in person. What Roxie doesn't realize is that Fifth Avenue happens to be the one person she would have never expected to meet.

While in London; Nathan Hendrickson and his band mates Paul, Calvin and Landon are busy writing songs for their band's next album. However after another recent run in with the London Police; Nathan decides to not listen to his manager's, Scott's; request and goes to his aunt and uncle's pub The Smouldering Hog for a nice evening to himself. It is on that night, during an unexpected thunderstorm; Nathan and Roxie meet for the very first time. However, the very next day; when Roxie meets Paul, Calvin and Landon; Roxie ends up taking on possibly the greatest challenge of her life: becoming Fifth Avenue Square's new personal assistant. According to Paul, Calvin, Landon and Nathan; all Roxie really needed to do to prove herself worthy to get the position of becoming Fifth Avenue Square's new personal assistant was to help the boys with any tasks Scott assigned to the band while he was on his business trip. In return, Nathan and his band mates try to help Roxie in finding a publisher for her book. However, things get difficult when Roxie realizes that Nathan is the only one out of Fifth Avenue Square who hasn't come to her for any advice or his songs for the band's next album. With the help of Paul, Landon, Calvin and Nathan's cousins Annie and Tom; Roxie then comes up with the brilliant idea of having a water war in order to get Nathan to open himself up more to Roxie. Not only was the water war a brilliant success in Nathan and Roxie's relationship but it also brought Nathan and his band mates somewhat closer and taught Scott's assistant Lexie some mature responsibility and respect towards Fifth Avenue Square. However, Roxie still thinks that helping out Fifth Avenue Square with their songwriting and the water war is still not enough proof for Scott to deem Roxie worthy of being Fifth Avenue Square's new personal assistant. So Roxie's room mate and best friend; Cassie, convinces Roxie to have Nathan and his band mates fly Cassie over to London not only get a record deal with the same recording studio as Fifth Avenue Square but also be a contender to become Fifth Avenue Square's opening act for the band's next world tour.

As this is going on; Roxie and Nathan not only develop a close friendship with each other, but the two of them also develop a deep, romantic connection. Its not until issues start to arise for Roxie's dream of becoming an author that gives Nathan the idea to take Roxie on a midnight adventure. It is in that same midnight adventure that Roxie and Nathan realize their feelings for one another, but are too afraid to say something that might intentionally ruin their friendship. However things get a turn for the worse when Roxie informs the others that she has to return to New York for an interview with a major publisher by the end of the month.

This causes a huge rift between both Roxie and Nathan that Paul, Calvin, Landon, Cassie, Annie and Tom feel like the only way to solve this issue is to have Nathan try to convince Roxie to stay in the UK. However, Nathan realizes no matter how many times he will try to convince Roxie to not go back to New York; it won't make things better between the two of them. So, Nathan; being the rebel that he is, goes to the airport and not only tries to stop Roxie from leaving the UK but also convinces Roxie to go after her dream of becoming an author a reality. Nathan also promises that he will have Scott find a way to bring Roxie back to the UK once she is done working on getting her book published. However, Roxie convinces Nathan that the process of getting a book published takes a lot of time so there could be a slight chance that Roxie could never come back to the UK in time for the release of Fifth Avenue Square's next album. But despite the fact of being several miles away from each other, Nathan and Roxie decide to give their chance of having a real relationship a shot. However a sudden surprise happens when Annie decides to go to New York to visit Roxie. Will the sudden news ruin Roxie and Nathan's chances of being together? One thing for sure is that when it comes to getting your dreams accomplished its a rocky road to make that dream a reality.