we cannot open the workbook because you didn't extract the data, and we can't connect to your datasource.
But regarding your problem, my guess would be that your [Pick Up Date] dimension is a datetime.
For example, in [Pick Up Date] <= [Choose an End Date] if your parameter returns 2018-10-31 and you have a row with a Pick Up Date of 2018.10.31:9:30:00, it will not return True because 9 hour is not <= 0 hour.
So your solution might be to trunc your Pick Up Date to day. DATETRUNC('day', [Pick Up Date] )
Thank you guys! Unfortunately, the packaged workbook was too large to attach, but it looks like Michel's suggestion worked!