[3] The series opens at Felicity's high school graduation, where she asks Ben Covington, a classmate on whom she has a crush, to sign her yearbook.

Moved by his comment that he wished they had gotten to know each other further, she changes her education plans completely, deciding to follow Ben to New York rather than attend Stanford University as a pre-med student.

Eventually, the two develop a romantic relationship, and the love triangle among Felicity, Ben, and Noel forms the basic dramatic conflicts in the show throughout the series.

A recurring episode opener of the show is a stark camera shot of Felicity sitting in a dormitory room or apartment holding a tape recorder, recalling events in order to make a cassette tape to send to an old friend named Sally Reardon (voiced by Janeane Garofalo).

Like NYU, UNY is located in Greenwich Village near Washington Square Park, and the school is an important part of the show.

[4] In 1999, a publicly hyped young writer for the show, Riley Weston, was disclosed as a fraud for claiming to be much younger than she truly was.

At the age of 32, she began marketing herself to television studios as a recent high school graduate, passing off her husband as her older brother.

[7] In the summer of 1999, after filming the first season,[8] Felicity star Russell—known for what The New York Times described as "[t]hat glorious head of voluminous golden backlit hair"[9]—sent the show's producers a photo wearing a short-haired wig.

[10] Russell did not agree with the network's attribution of the ratings decline, telling Entertainment Weekly in 2000, "I think that's a pretty lame excuse.

I think a lot more than a haircut was deciding the ratings [last year]", which – according to a September 29, 2023, Time magazine article – included the timeslot change, which cost the show one third of its viewers.