Podrías intentar
SELECT a.*, b.*
FROM a INNER JOIN b ON a.B_id = b.B_id
WHERE a.flag IS NULL AND b.date < NOW()
UNION
SELECT a.*, b.*
FROM a INNER JOIN b ON a.B_id = b.B_id
INNER JOIN c ON a.C_id = c.C_id
WHERE a.flag IS NOT NULL AND c.date < NOW()
