Episode 52 of "Will and Grace"
s03e06 Love Plus One
Title: Love Plus One
Original Air Date: 11/09/2000 on NBC
Plot Outline:
Grace rejects an ex-boyfriend's suggestion that she participate with him and his girlfriend in a romantic escapade but when she confides in Will and Karen -- who fall down laughing at the prospect -- the conservative Grace considers throwing caution to the wind. Meanwhile, Will tries to help a newly employed Jack meet a customer at a clothing store by prompting him with witty lines like a latter-day Cyrano de Bergerac.
