Bailey Pickett was born on her farm in Kettlecorn, Kansas. She is the seventh oldest of ten girls and didn't want to just be a farmer's wife. Before arriving on the S.S. Tipton, she dated Moose, but was heartbroken when they broke up. After living in a small town for so long, Bailey decided to follow her dreams and explore the world. She joined the S.S. Tipton, where she would experience several new adventures with plenty of new people, including Cody Martin, who later became her second boyfriend. She is very close to the country lifestyle.
In the first season of The Suite Life on Deck, we meet Bailey, a smart, kindhearted girl from Kettlecorn, Kansas. Because she longs to see the world, she enrolls in Seven Seas High. She has to do so as a boy, since every girl already has a roommate. She originally becomes Zack's roommate. Zack soon finds out Bailey's secret, and developes an attraction to her, therefore agreeing to keep her secret. However, Mr. Moseby figures out Bailey's true identity and it seems that Bailey won't have a place to stay until London (who had bribed her original roommate to leave) is unwillingly forced to accept Bailey as her new roommate.
She is described as nice, smart, fun and loving. Bailey is always looking out for other people's feelings, which shows how sensitive she is. She is a sweet, down-to-earth girl who also has a romantic side to her personality. She adores her boyfriend Cody. Though she fell in love with Cody's sensitive, smart personality, in "The Line of Duty", Cody says they will have to meet after curfew due to lack of quality time, and she says she likes the bad boy Cody. Bailey is really helpful and she always finishes her homework on time and has never missed a day of school as shown in "Senior Ditch Day". She is persistent, as seen in "Smarticle Particles" when she never gave up trying to tutor London.