SELECT a.ID,
DATEADD( s, RAND( CONVERT( INT, CAST( NEWID() AS BINARY(16) ), 1)) * 252460800, '20080101' ) AS dt
FROM
(VALUES (1), (2), (3), (4), (5), (6), (7), (8), (9), (10), (11), (12), (13), (14), (15)) AS A (ID)
CROSS JOIN
(VALUES (1), (2), (3), (4), (5), (6), (7), (8), (9), (10),
(11), (12), (13), (14), (15), (16), (17), (18), (19), (20),
(21), (22), (23), (24), (25), (26), (27), (28), (29), (30)) AS B(C)
ORDER BY NEWID()