The series follows Patty Greene (Sarah Jessica Parker) and Lauren Hutchinson (Amy Linker), two awkward teenage girls desperate to fit in at Weemawee High School.

Created by former Saturday Night Live writer Anne Beatts, the pilot introduces an eclectic group of eight freshmen on their first day at Weemawee High School.

[1][2] The series was much acclaimed by critics at the time for its realistic look at teenage life, reflecting a sensibility somewhat similar to the John Hughes teen comedies of later years.

[4] Patty Greene (Sarah Jessica Parker) is clever and seemingly well-adjusted, but feels awkward and like a social misfit (i.e. a square peg) when with the "popular" students.

Though seemingly off in his own world most of the time, Johnny states that he "[does not] do drugs and isn't a hippie" and on more than one occasion displays unexpected intuition and empathy, particularly regarding Marshall and the girls.

Though perhaps socially inept ("I’m going to ignore that because, frankly, I don't get it"), Muffy's unawareness and/or lack of concern with her failure to fit in with the popular kids is in stark contrast to the motivation of the show's protagonists, and does not stop her from relentless involvement in school activities.

She shows her partial disdain for Patty and Lauren by calling them "String Bean" and "Fang" and the "gruesome twosome"[5] An ongoing gag throughout the series is Muffy's fundraising for Weemawee's adopted "little Guatemalan child," Rosarita.

As the series progresses, Muffy's charitable intentions become more and more frivolous, asking the school community to provide the girl with her own apartment away from her parents, cable TV, a second pair of culottes, swimwear, a split-level duplex, and finally, her own cleaning lady.

[6] Before the opening credits and theme song begin, every episode starts with the following dialogue appearing in a montage of stills from the school: Lauren: Listen.

[6] Because Norwalk was twenty miles from Norman Lear's studio office and CBS Television in Los Angeles, it was hard for the producers or network to know what was happening during filming.

The highest audience share Square Pegs ever received was a 24, which now [in 2020] would make you the queen of Hollywood, but was considered inadequate for CBS, then the leading 'Tiffany network.

'"[6] The show's opening and closing theme songs, "Square Pegs" and an untitled instrumental (reminiscent of "Chopsticks") composed by Tom Scott, are performed by The Waitresses.

On August 27, 2013, it was announced that Mill Creek Entertainment had acquired the rights to various television series from the Sony Pictures library including Square Pegs.