Only empty columns (i.e. empty String) are mapped to null when Super CSV reads the CSV - a space will be read as a space. This is because whitespace is meant to be important in RFC4180, the CSV mimetype specification.
So Optional
won't bypass the next processor for a space. You can use this processor setup instead:
new Optional(new Token(" ", null, new ParseDate("MM/dd/yyyy",true)));
This will return null
if it encounters null (i.e. empty String in the CSV) or a single space, and bypass trying to parse it as a date.
You could also enable the surroundingSpacesNeedQuotes preference to get around this, but just be aware that this will also strip out any leading/trailing spaces - which you might not want.