Yes you should enter a date. There are many problems with the new version of It's Deductible. TurboTax is working on improvements but has not determined when they will be ready. In the meantime, if you want to revert back to the classic version, use this procedure:

If you want to get back to the classic version of It's Deductible to make entries, 

Click this link: https://itsdeductibleonline.intuit.com/Logout.htm

The page will show that you are logged out. At the top of the page is a small sign-in button.

Click sign-in and use your ItsDeductible login credentials to get access to the classic version of your account. 

You may need to log off the new version before logging in to the classic version.

Bookmark the link above for future reference.