This is the first single from 2010 American Idol winner Lee DeWyze's debut album Live It Up. He debuted the song on the October 13, 2010 edition of On Air with Ryan Seacrest.
DeWyze sings about "always landing on my feet" and "something's watching over me like sweet serendipity." The lyrics about fate share similar sentiments to Doris Day's 1956 Oscar winning song, "Que Sera, Sera (Whatever Will Be, Will Be)
DeWyze recorded this song and the other tracks on Live It Up, while he was on the "American Idols Live!" tour in the summer of 2010.
DeWyze previously planned to release the album's title track as his first single release, but changed it few hours before it came out. "There is change of plans with the single. We're holding off on Live It Up and going to go with one no one has heard - Sweet Serendipity," he wrote on Twitter early on October 13th. During a telephone interview with Ryan Seacrest, the radio host asked the singer why he changed his mind. DeWyze explained that he played the song for a lot of people, and he felt that "Serendipity" is the one that stood out the most. He also stated that while there is a whole array of different songs on the album, its fun vibes in it can make people dance to or sing along with it.
DeWyze co-wrote all but one song on Live it Up, and as such became the very first American Idol winner to have writing credit on a first single. "To see my name listed in the credits on each song was really important to me because I'm a songwriter," DeWyze said before adding: "I love stories in songs and always try to write from an honest place. It's about capturing emotion, so that when you listen, it takes you back to that place. My best memories are all connected to music and I want to create those moments for other people."