Ryan and Brian are big baseball fans (Ryan of the Los Angeles Dodgers and Brian of the Boston Red Sox). During the baseball season, many side conversations shift to baseball, especially if either of their preferred teams has done anything notable. In 2018, the Red Sox and Dodgers faced off in the 2018 World Series, with the Red Sox winning the series four games to one. On the next episode of Fill Me In (Episode 169, 11/6/18), Brian welcomed guest cohost Angela Halsted, claiming that Ryan was quarantined for his own safety.

During the weekly contests, Ryan and Brian use a password to secure the validity of contest entries. The password has most frequently been the name of a baseball player whom one or both cohosts particularly dislikes. For a long time, the password was "Papelbon" (for former Red Sox relief pitcher Jonathan Papelbon), and currently, the password is "Darvish" (for former Los Angeles Dodgers starting pitcher Yu Darvish).

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