Types
This was too long for a comment to prince:
Enums are bad in python except for very specific cases, while this may be one of them, I would generally recommend against Enums. Enums are not useful code, they don't make the code clearer. Python doesn't have a switch statement.
First learn the built-in types, a flip can be described with a Boolean (bool) [note: booleans are a subtype of ints]. If you have more options (like a dice roll), then use whole numbers (int). If you randomly choose a winner from a pool of players, use a set of strings (str).
If you need to map an input to an output, rather than a long if chain, use Dictionaries (dict):
result = {
False: "It's tails.",
True: "It's head."
}
choice = bool(random.randint(0, 1))
# or bool(random.getrandbits(1))
# or random.choice({True,False})
print(result[choice])
While it might seem ridiculous to use a dictionary in this case, it will make sense if you take a deck of card for example.
result = {
1: "as",
2: "two",
3: "three",
4: "four",
5: "five",
6: "six",
7: "seven",
8: "eight",
9: "nine",
10: "ten",
11: "jack",
12: "queen",
13: "king"
}
# or
"""
result = {
1: "as",
**{i: str(i) for i in range(2,11)}
11: "jack",
12: "queen",
13: "king"
}
"""
colors = {"clubs", "diamonds", "spades", "hearts"}
your_card = bool(random.randint(0, 13))
ai_card = bool(random.randint(0, 13))
print(f"Your card is the {result[your_card]} of {random.choice(colors)}")
print(f"Your card is the {result[ai_card]} of {random.choice(colors)}")
print(f"The winner is {'you' if your_card > ai_card else 'ai'}")
Of course, in those cases, it isn't obvious to find the string if you have the number, if it is trivial to make a function that can do the conversion, make a function.
My top advice is Don't make long if chains and avoid enums until you know all built in types
°[note: code not tested]