Just change your command_show() function to this, if you don't use dict.items() then you will only get the keys(not both keys and values):
def command_show(calendar):
    for (date, event) in calendar.items():
        print(date+':')
        for i in enumerate(event):
            print('    '+str(i[0])+': '+i[1])
Output:
2015-10-29:
    0: Python class
    1: Change oil in blue car
2015-10-12:
    0: Eye doctor
    1: lunch with sid
About why am I doing this:
for i in enumerate(event):
    print('    '+str(i[0])+': '+i[1])
As you can see, I'm using enumerate() function here. From the document:
Return an enumerate object. iterable must be a sequence, an iterator, or some other object which supports iteration.
  The __next__() method of the iterator returned by enumerate() returns a tuple containing a count (from start which defaults to 0) and the values obtained from iterating over iterable.
So it will return something like [(0, 'Python class'), (1, 'Eye doctor'), (2, 'lunch with sid')] if the evernt is ['Python class', 'Eye doctor', 'lunch with sid']. 
Now we have [(0, 'Python class'), (1, 'Eye doctor'), (2, 'lunch with sid')], when we use for loop on it like for i in enumerate(event), i will be (0, 'Python class') at the first loop, and (1, 'Eye doctor') at the second loop, etc.
And then, if you want to print something like 0: Python class(there is some spaces in front of the sting), we need manually put the spaces like '    '+(+ can join strings here, for example, 'foo'+'bar' is foobar). 
Then, because i is a tuple, I'm using slice. i[0] can get the first element in that tuple, i[1] can get the second, etc.
Because i[0] is a integer, and we can't just do something like 0 + 'foobar'(will raise TypeError: unsupported operand type(s) for +: 'int' and 'str'). So we need use str() function to covert it to string. And then...maybe you'll understand.
Also you can do something like:
for num, event in enumerate(event):
    print('    '+str(num), event, sep=': ')
More clear? for num, event in enumerate(event) will give something like num = 0, evert = 'Python class' at the first loop, and...as I said.
About sep, you could check the document for more details.