第 3 季，第 6 集: Grace (Debra Messing) rejects an ex-boyfriend's (guest star Jeremy Piven, "Cupid") suggestion that she participate with him and his girlfriend (guest star Maria Pitillo, NBC's "Providence") in a romantic escapade but when she confides in Will (Eric McCormack) and Karen (Megan Mullally) - who falls down laughing at the prospect - the conservative Grace considers throwing caution to the wind. Meanwhile, Will tries to help a newly employed Jack (Sean Hayes) meet a customer (guest star Patrick Dempsey, "Scream 3") at a clothing store by prompting him with witty lines like a latter-day Cyrano de Bergerac.