Model Shalom Harlow appeared in the feel-good film as Judy Green, one of Ben’s colleagues who had a role in setting him up with Andie. Harlow, one of the most famous supermodels of the 1990s, hasn’t done a ton in film or television since the 2003 flick, but has worked with countless designers and brands, like Prada, Chanel, Balmain, Christian Dior, Marc Jacobs, Gucci, and more, throughout the last two decades.