 His next film roles in 1998 were Kissing a Fool , Six Days Seven Nights , and Apt Pupil . In Kissing a Fool , a romantic comedy , Schwimmer played Max , a dapper , smart @-@ mouthed ladies ' man . Mick LaSalle of the San Francisco Chronicle wrote , " Fans of the sitcom Friends may be surprised by David Schwimmer in Kissing a Fool . [ ... ] Take it from someone who has never seen Friends and comes at Schwimmer with no preconceptions : He does just fine . As a TV sports reporter in Kissing a Fool , he oozes the command and self @-@ satisfaction of a young , successful man " . The film was critically and financially unsuccessful . In Six Days Seven Nights , he played the boyfriend of Anne Heche 's character . In Apt Pupil , adapted from a novella of the same name by Stephen King , he had a supporting role as a school guidance counselor . " I was scared of the part " , Schwimmer said , " but I wanted to be part of the movie " . At the time , he noted it was a " little frustrating " that people would typecast him due to his role on Friends . He subsequently appeared opposite Woody Allen and Sharon Stone in Alfonso <unk> 's straight @-@ to @-@ cable comedy Picking Up the Pieces ( 2000 ) . 
