"The Whole Point of Being Roommates" focuses on "Chicago Fire's" Gabby Dawson, who has a tendency to overstep boundaries. This episode, in particular, highlights that aspect of her character as it builds the relationship between Dawson and a teenage girl she rescued in the previous episode. While the girl, Bria, is in the hospital, Dawson asks her a few questions about her circumstances, and becomes suspicious after Bria is dodgy with her answers.

This is when Dawson really starts to step over the line. She begins following Bria, eventually offering her a ride home to try to find out where she lives. After Bria enters her house, Dawson forces her way inside and discovers that Bria's dad is severely addicted to prescription painkillers, caused by an injury at work. Dawson offers to help Bria, and ends up being called back after the father has a seizure due to the drugs. Dawson tries to help, but Severide ends up calling 911, which starts an investigation into Bria's living situation and causes her to run away. Dawson's reckless disregard for the rules and other people's feelings ends up putting Bria's safety at risk, making "The Whole Point of Being Roommates" an uncomfortable episode to watch.