Gail is a Guidance Counselor at Greendale Community College. Her first and only appearance on the show was in the Season One episode "The Politics of Human Sexuality". She was portrayed by actress/comedian Liz Cackowski.
In the study group's first year together at Greendale, Annie along with Shirley and Britta broke into Dean Pelton's office. She needed to get a good look at an anatomically correct male mannequin she was to use in a condom demonstration at the STD Fair. Although they managed to get a quick peek at the mannequin, the trio was caught by campus security while in the midst of the act. Due to the potentially sensitive nature of the crime, the school guidance counselor Gail was brought in to insure that the interrogation of the three suspects by Dean Pelton was handled in a legally appropriate manner. Since the word "penis" was going to be used liberally in the discussion, Gail suggested that everyone in the room say the word together in order diffuse any awkwardness. Everyone says the word with the exception of Annie which Security Guard Cackowski points out.
Gail interrupts Pelton questioning the suspects about the incident and redirects the conversation to Annie. Intrigued by her refusal to say the word "penis", she tried to get Annie to open up about her prudishness. All eyes turned to Annie who was assured by Gail that it was a judgement free zone and encouraged her to express how she felt. Annie then declared to everyone in the room that she's uncomfortable saying that word and is fine being repressed about her own sexuality. She states that if more people thought as she did there probably wouldn't need to be an STD fair in the first place. She then storms out of the office and added that she didn't understand what the big deal was after having seen the mannequin. She described it as "a giant thumb in a turtleneck" which Gail considers for a moment before nodding her head in agreement of Annie's assessment.
Liz Cackowski worked on "Community" in Season One as script supervisor. She also wrote two episodes of the show, including the one featuring her first and only appearance onscreen "The Politics of Human Sexuality" and the Christmas themed episode "Comparative Religion". Her brother is the actor/comedian Craig Cackowski who has the recurring role of Officer Cackowski on the show.