[8] Weil traveled frequently to New York City for professional auditions and acted in productions both off-Broadway and in Philadelphia's theatrical community before pursuing her film and television career.

[9][10] Her first appearance on network television was in a 1995 episode of the New York-based CBS soap opera As the World Turns, where she played an unnamed student in a science class.

An alumna of Columbia University, Weil received her first major feature film role co-starring with Kevin Bacon in Stir of Echoes.

After her work in Whatever and Stir of Echoes, Warner Bros. signed Weil to a talent holding deal and she moved to Los Angeles, where she guest-starred on series produced by that studio, including ER and The West Wing, before being cast on Gilmore Girls.

[10] In 2006, Weil was featured in the horror themed short film, Grace, in which her character suffers a miscarriage, yet decides to carry the baby to term with terrifying results.

[14] In March 2011, Weil was cast as Amanda Tanner, a White House aide, in ABC's Scandal, a series written and produced by Shonda Rhimes.

[15] Weil played a supporting role in the horror film Smiley, and started 2013 as a recurring guest star in the last half of the only season of Amy Sherman-Palladino's ABC Family series Bunheads as Milly, the sister of Truly Stone.

[19] In February 2014, Weil was cast as Bonnie Winterbottom, an assistant to Annalise Keating (Viola Davis) in the ABC series How to Get Away with Murder,[20] which premiered during the 2014–15 television season.

[21] She also reprised her role as Paris Geller in the "Winter" and "Spring" episodes of the Netflix revival series Gilmore Girls: A Year in the Life.