How to update rows with a random date

Use this to generate a smalldatetime between 01 Jan 1900 and 06 Jun 2079 (not checked, SQL not installed)

DATEADD(day, (ABS(CHECKSUM(NEWID())) % 65530), 0)

NEWID is better then trying to use RAND: RAND does not generate different values row in a single SELECT or UPDATE (well it didn't in SQL 2000, in case behaviour has changed).

Edit: like this

UPDATE
  table
SET
  datetimecol = DATEADD(day, (ABS(CHECKSUM(NEWID())) % 65530), 0)

Edit: changed 65535 to 65530 and added ABS to avoid overflow at upper limit of range

I will complement the answers below,

SELECT DATEADD(DAY, ABS(CHECKSUM(NEWID()) % 3650), '2000-01-01')
FROM your_table

This generates dates starting from 2000-01-01, and you can change the amount of days in the modulus value, I put 3650 (about 10 years), this approach doesn't overflow.

If you want to update, then

UPDATE your_table
SET your_date_field = DATEADD(DAY, ABS(CHECKSUM(NEWID()) % 3650), '2000-01-01')
WHERE your_conditions

The following code will fill the StartDate column of the FiscalYear table with random dates between two given dates:

-- First, let's declare the date range.
DECLARE @date_from DATETIME;
DECLARE @date_to DATETIME;

-- Set the start and date dates. In this case, we are using
-- the month of october, 2006.
SET @date_from = '1985-10-14';
SET @date_to = '2009-04-27';

UPDATE FiscalYear SET StartDate =  
(
    -- Remember, we want to add a random number to the
    -- start date. In SQL we can add days (as integers)
    -- to a date to increase the actually date/time
    -- object value.
    @date_from +
    (
        -- This will force our random number to be >= 0.
        ABS
        (
            -- This will give us a HUGE random number that
            -- might be negative or positive.
            CAST(CAST(NewID() AS BINARY(8)) AS INT)
        )

        -- Our random number might be HUGE. We can't have
        -- exceed the date range that we are given.
        -- Therefore, we have to take the modulus of the
        -- date range difference. This will give us between
        -- zero and one less than the date range.
        %

        -- To get the number of days in the date range, we
        -- can simply substrate the start date from the
        -- end date. At this point though, we have to cast
        -- to INT as SQL will not make any automatic
        -- conversions for us.
        CAST((@date_to - @date_from) AS INT)
    )
)

I was looking for a question similar to this that also generated a random time and I found this script. Thought it might be useful here:

DECLARE @DateFrom DATETime = '2001-01-01'
DECLARE @DateTo DATeTime = '2013-11-30'
DECLARE @DaysRandom Int= 0
DECLARE @MillisRandom Int=0

--get random number of days

select @DaysRandom= DATEDIFF(day,@DateFrom,@DateTo)
SELECT @DaysRandom = ROUND(((@DaysRandom -1) * RAND()), 0)

--get random millis
SELECT @MillisRandom = ROUND(((99999999) * RAND()), 0)

SELECT @DateTo = DATEADD(day, @DaysRandom, @DateFrom)
SELECT @DateTo = DATEADD(MILLISECOND, @MillisRandom, @DateTo)
SELECT @DateTo

I got it from here: http://crodrigues.com/sql-server-generate-random-datetime-within-a-range/

Using the code below you can get a random integer between @Min (1) and @Max (365), then using the dateadd funection you can create random dates in the last year.

CREATE VIEW vRandNumber
AS
SELECT RAND() as RandNumber
GO

CREATE FUNCTION RandNumber(@Min int, @Max int)
RETURNS int
AS
 BEGIN
 RETURN round(@Min + (select RandNumber from vRandNumber) * (@Max-@Min),0)
 END
GO

Update table1
set theDate = dateadd(d,0-dbo.RandNumber(1,365),getdate())

you can try getting a random number (positive or negative) then adding that number to a date (possibly system date).

For example (I don't have access to sqlserver right now so I could not verify syntax)

DATEADD(day, DATEDIFF(day, 0, GETDATE()) - 1 - FLOOR(RAND(CAST(NEWID() AS binary(4))) * 365.25 * 90), 0)