Why can't I check if a 'DateTime' is 'Nothing'?

In any programming language, be careful when using Nulls. The example above shows another issue. If you use a type of Nullable, that means that the variables instantiated from that type can hold the value System.DBNull.Value; not that it has changed the interpretation of setting the value to default using "= Nothing" or that the Object of the value can now support a null reference. Just a warning... happy coding!

You could create a separate class containing a value type. An object created from such a class would be a reference type, which could be assigned Nothing. An example:

Public Class DateTimeNullable
Private _value As DateTime

'properties
Public Property Value() As DateTime
    Get
        Return _value
    End Get
    Set(ByVal value As DateTime)
        _value = value
    End Set
End Property

'constructors
Public Sub New()
    Value = DateTime.MinValue
End Sub

Public Sub New(ByVal dt As DateTime)
    Value = dt
End Sub

'overridables
Public Overrides Function ToString() As String
    Return Value.ToString()
End Function

End Class

'in Main():

        Dim dtn As DateTimeNullable = Nothing
    Dim strTest1 As String = "Falied"
    Dim strTest2 As String = "Failed"
    If dtn Is Nothing Then strTest1 = "Succeeded"

    dtn = New DateTimeNullable(DateTime.Now)
    If dtn Is Nothing Then strTest2 = "Succeeded"

    Console.WriteLine("test1: " & strTest1)
    Console.WriteLine("test2: " & strTest2)
    Console.WriteLine(".ToString() = " & dtn.ToString())
    Console.WriteLine(".Value.ToString() = " & dtn.Value.ToString())

    Console.ReadKey()

    ' Output:
    'test1:  Succeeded()
    'test2:  Failed()
    '.ToString() = 4/10/2012 11:28:10 AM
    '.Value.ToString() = 4/10/2012 11:28:10 AM

Then you could pick and choose overridables to make it do what you need. Lot of work - but if you really need it, you can do it.