After a bit of searching, I found two libraries that met my needs!

The first is python-inquirer, a Python port of Inquirer.js, a CLI library used by projects like Yeoman. I found this library to have a really nice API (built on top of blessings) but lacks polish when it comes to design/features.

The second (which I will be using) is whaaaaat, another Python port of Inquirer. This library offers functionality much closer to the original Inquirer.js and is exactly what I needed. The API is less clean than that of python-inquirer, however.

Examples:

python-inquirer example:

from pprint import pprint
import inquirer

questions = [
    inquirer.List(
        "size",
        message="What size do you need?",
        choices=["Jumbo", "Large", "Standard", "Medium", "Small", "Micro"],
    ),
]

answers = inquirer.prompt(questions)
pprint(answers)

whaaaaat example:

from whaaaaat import prompt, print_json, Separator

questions = [
    {
        "type": "list",
        "name": "theme",
        "message": "What do you want to do?",
        "choices": [
            "Order a pizza",
            "Make a reservation",
            Separator(),
            "Ask for opening hours",
            {"name": "Contact support", "disabled": "Unavailable at this time"},
            "Talk to the receptionist",
        ],
    },
    {
        "type": "list",
        "name": "size",
        "message": "What size do you need?",
        "choices": ["Jumbo", "Large", "Standard", "Medium", "Small", "Micro"],
        "filter": lambda val: val.lower(),
    },
]

answers = prompt(questions)
print_json(answers)