What returns your statement DateTime.Now.ToString()?
What language and regional settings do you expect from your SQL Server?
??? , .NET MM/dd/yyyy, SQL Server dd/MM/yyyy ( ).
SQL Server:
DECLARE @test TABLE (smalldate SMALLDATETIME)
INSERT INTO @test VALUES ('02/21/2010 22:00:32')
SELECT * FROM @test
, .NET DateTime.Now.ToString() - ? SQL Server ?
ISO-8601 (YYYYMMDD) - SQL Server - ?
DECLARE @test TABLE (smalldate SMALLDATETIME)
INSERT INTO @test VALUES ('20100221 22:00:32')
SELECT * FROM @test