Always found it still cumbersome to add calendar entries ... so this app, QuickCal (http://smellypuppy.com/wp/?page_id=29) is lovable. Type in: Date with Winona tomorrow at 7pm till 9pm and a calendar entry for Feb 14, 7pm to 9pm called "Date with Winona" is added to your Calendar. It's free!
You can also use Google Notifier (which sits on the menu bar) to quick add events ala Google Calendar style, like QuickCal.
