Caitlin got her first job at The Big Squeeze after being turned down in every interview. Jen offered her the job, once she was hired at the Penalty Box. At first she was a little hesitant because she hand to wear a lemon cap and work in a stand literally designed as a lemon. She overcame her risks of humiliation and continues to work at her job. The Big Squeeze is also the gang's main hang out where they discuss the latest gossips, Jonesy's new findings of a job and whatnot.