Want to order on two columns but not the usual way
SELECT *
FROM Mytable
ORDER BY
   userID, Date


I assume Date is really a date/time type and not varchar...

Edit, after clarification:

Untested

SELECT
    M.*
FROM
    ( --one row for each user
    SELECT MIN(Date) AS FirstUserDate, userID
    FROM MyTable
    GROUP BY userID
    ) foo
    JOIN
    MyTable M ON foo.userID = M.userID
ORDER BY
    foo.FirstUserDate, M.userID, M.Date;