since you are using SQL Server, why not change the data type to VARCHAR(100)?
To work around this error without changing the datatype, the TEXT or NTEXT column needs to be converted to VARCHAR or NVARCHAR when used in either the ORDER BY clause or the GROUP BY clause of a SELECT statement. eg, which is alittle bit messy
SELECT CAST(email AS NVARCHAR(100)) email,
COUNT(CAST(email AS NVARCHAR(100))) AS NumOccurrences
FROM Booking
GROUP BY CAST(email AS NVARCHAR(100))
HAVING COUNT(CAST(email AS NVARCHAR(100))) > 1
- SQL Server Error Messages – Msg 306