You might want to check if any item is in the play queue:
Code:
TEXT EVENT {
  if ($play(0)) { notice $nick I have $v1 items in my playback queue }

  YOUR CODE, e.g. /play to $nick
}


In case you want to check for a specific file, you'll have to loop all items in the play queue, for example:
Code:
TEXT EVENT {
  var %n = 1, %queued = 0
  while ($play(%n)) {
    if ($nopath($play(%n).fname) == help.db) { inc %queued }
    inc %n
  }
  if (%queued) { notice $nick I have $v1 requests for "help.db" in my playback queue }

  YOUR CODE, e.g. /play to $nick
}