Действительно простой способ в SSMS - это сделать:
INSERT INTO Table (FK_id, Somedate)
VALUES (3, GETDATE())
GO 5000
Но все равно это несколько вставок.
Вы можете выполнить одну вставку следующим образом:
WITH
L0 AS (SELECT 1 AS c UNION ALL SELECT 1),
L1 AS (SELECT 1 AS c FROM L0 A CROSS JOIN L0 B),
L2 AS (SELECT 1 AS c FROM L1 A CROSS JOIN L1 B),
L3 AS (SELECT 1 AS c FROM L2 A CROSS JOIN L2 B),
L4 AS (SELECT 1 AS c FROM L3 A CROSS JOIN L3 B),
L5 AS (SELECT 1 AS c FROM L4 A CROSS JOIN L4 B),
Nums AS (SELECT ROW_NUMBER() OVER(ORDER BY (SELECT NULL)) AS n FROM L5)
INSERT INTO Table(FK_id, Somedate)
SELECT TOP (5000)
FK_id, Somedate
FROM Nums
CROSS APPLY (VALUES (3, GETDATE())) t (FK_id, Somedate)
ORDER BY n