With the "If" operator, both return value must be of the same type. In this case, the If returns a DateTime for both true and false. You can see this by doing the below (it won't compile).
If(True, 123, "aaa")
So you don't get a real Nothing. Instead, just return a nullable.
Dim newDateTime As Nullable(Of DateTime) = If(myDateTime.Equals(DateTime.MinValue), New Nullable(Of DateTime), myDateTime)
Or like Arman said
Dim newDateTime As Nullable(Of DateTime) = If(myDateTime.Equals(DateTime.MinValue), CType(Nothing, DateTime?), myDateTime)
Better yet, don't try to put everything on one line ;)