Should I or Should I? may refer to:

 "Should I" (song), a 1965 song by Chad & Jeremy, later covered by the Hep Stars
 "Should I?" (song), a song from the 1930 film Lord Byron of Broadway
 "Should I?", a song by Rihanna featuring J-Status from the 2006 album A Girl like Me

See also
 Should I Stay or Should I Go (disambiguation)