You should never change the date on your watch between the hours of 10PM and 2AM!
The reason: The date mechanism containing the gears start engaging to change the date at 10PM on most watches, it changes at 12AM and the gears will dis-engage completely by 2AM. If you try and change the date during these times turning the crown will give some resistance and the date will not change, if forced, either the crown, the date mechanism or both will break.
You can and should wind your automatic watch!
The reason: An automatic watch normally winds through movement.Depending on the model, the watch will have either a 38 or 48 hour power reserve. This means if the watch is not worn, it will keep running until the power reserve runs out. Only wind the watch if it has stopped and the time/date is being reset. When resetting the time after the watch has stopped; First, pull the crown out to set the correct date and time, then push the crown in, back to the original position to start the watch. Lastly, turn the crown away from you, 15 turns (Don't worry you can't over-wind the watch). For watches with a screw down crown, wind the watch before screwing down the crown. The quick wind will start the second hand and watch will continue to wind and become fully wound through movement.