Frank Whaley stars as Jim Dodge, a 21-year-old con-man who goes from job to job but likes to put on a facade of success. As Career Opportunities begins, he has just been fired from another job and has been hired by the local Target store manager (John Candy) as the night cleanup boy. But then Jim discovers that he is not the only person in the store. Also there is rich girl Josie McClellan (Jennifer Connelly) who is spending the night in the store to get her father worried about her. Although Jim knew Josie in high school, when Josie wouldn’t even give him the time of day, here they fall in love. But just at the moment when Jim and Josie plan to run away together, two low-rent comic thieves — Nestor Pyle (Dermot Mulroney) and Gil Kinney (Kieran Mulroney) — break into the store and Jim and Josie decide to stick it out, saving the store from the bumbling crooks.