diff --git a/copier/config/user_data.py b/copier/config/user_data.py
index d0265e9ba..c2b6c93cf 100644
--- a/copier/config/user_data.py
+++ b/copier/config/user_data.py
@@ -2,6 +2,7 @@
 
 import json
 import re
+import sys
 from collections import ChainMap
 from functools import partial
 from pathlib import Path
@@ -10,12 +11,17 @@
 import yaml
 from jinja2 import UndefinedError
 from jinja2.sandbox import SandboxedEnvironment
-from plumbum.cli.terminal import ask, choose, prompt
-from plumbum.colors import bold, info, italics
+from plumbum.cli.terminal import ask, choose
+from plumbum.colors import bold, info, italics, reverse, warn
+from prompt_toolkit import prompt
+from prompt_toolkit.formatted_text import ANSI
+from prompt_toolkit.lexers import PygmentsLexer
+from prompt_toolkit.validation import Validator
+from pygments.lexers.data import JsonLexer, YamlLexer
 from yamlinclude import YamlIncludeConstructor
 
-from ..tools import get_jinja_env, printf_exception
-from ..types import AnyByStrDict, Choices, OptStrOrPath, PathSeq, StrOrPath
+from ..tools import force_str_end, get_jinja_env, printf_exception, to_nice_yaml
+from ..types import AnyByStrDict, Choices, OptStr, OptStrOrPath, PathSeq, StrOrPath
 from .objects import DEFAULT_DATA, EnvOps, UserMessageError
 
 __all__ = ("load_config_data", "query_user_data")
@@ -43,6 +49,73 @@ class InvalidTypeError(TypeError):
     pass
 
 
+def ask_interactively(
+    question: str,
+    type_name: str,
+    type_fn: Callable,
+    secret: bool = False,
+    placeholder: OptStr = None,
+    default: Any = None,
+    choices: Any = None,
+    extra_help: OptStr = None,
+) -> Any:
+    """Ask one question interactively to the user."""
+    # Generate message to ask the user
+    message = ""
+    if extra_help:
+        message = force_str_end(f"\n{info & italics | extra_help}{message}")
+    emoji = "🕵️" if secret else "🎤"
+    message += f"{bold | question}? Format: {type_name}\n{emoji} "
+    lexer_map = {"json": JsonLexer, "yaml": YamlLexer}
+    lexer = lexer_map.get(type_name)
+    # Use the correct method to ask
+    if type_name == "bool":
+        return ask(message, default)
+    if choices:
+        return choose(message, choices, default)
+    # Hints for the multiline input user
+    multiline = lexer is not None
+    if multiline:
+        message += f"- Finish with {reverse | 'Esc, ↵'} or {reverse | 'Meta + ↵'}\n"
+    # Convert default to string
+    to_str_map = {"json": lambda obj: json.dumps(obj, indent=2), "yaml": to_nice_yaml}
+    to_str_fn = to_str_map.get(type_name, str)
+    # Allow placeholder YAML comments
+    default_str = to_str_fn(default)
+    if placeholder and type_name == "yaml":
+        prefixed_default_str = force_str_end(placeholder) + default_str
+        if yaml.safe_load(prefixed_default_str) == default:
+            default_str = prefixed_default_str
+        else:
+            print(warn | "Placeholder text alters value!", file=sys.stderr)
+    return prompt(
+        ANSI(message),
+        default=default_str,
+        is_password=secret,
+        lexer=lexer and PygmentsLexer(lexer),
+        mouse_support=True,
+        multiline=multiline,
+        validator=Validator.from_callable(abstract_validator(type_fn)),
+    )
+
+
+def abstract_validator(type_fn: Callable) -> Callable:
+    """Produce a validator for the given type.
+
+    Params:
+        type_fn: A callable that converts text into the expected type.
+    """
+
+    def _validator(text: str):
+        try:
+            type_fn(text)
+            return True
+        except Exception:
+            return False
+
+    return _validator
+
+
 def load_yaml_data(
     conf_path: Path, quiet: bool = False, _warning: bool = True
 ) -> AnyByStrDict:
@@ -196,21 +269,19 @@ def query_user_data(
             # Get default answer
             answer = last_answers_data.get(question, default)
         if ask_this:
-            # Generate message to ask the user
-            emoji = "🕵️" if details.get("secret", False) else "🎤"
-            message = f"\n{bold | question}? Format: {type_name}\n{emoji} "
-            if details.get("help"):
-                message = (
-                    f"\n{info & italics | _render_value(details['help'])}{message}"
-                )
-            # Use the right method to ask
-            if type_fn is bool:
-                answer = ask(message, answer)
-            elif details.get("choices"):
-                choices = _render_choices(details["choices"])
-                answer = choose(message, choices, answer)
-            else:
-                answer = prompt(message, type_fn, answer)
+            extra_help = details.get("help")
+            if extra_help:
+                extra_help = _render_value(extra_help)
+            answer = ask_interactively(
+                question,
+                type_name,
+                type_fn,
+                details.get("secret", False),
+                _render_value(details.get("placeholder")),
+                answer,
+                _render_choices(details.get("choices")),
+                _render_value(details.get("help")),
+            )
         if answer != details.get("default", default):
             result[question] = cast_answer_type(answer, type_fn)
     return result
diff --git a/copier/tools.py b/copier/tools.py
index fefa99f28..b5ac0763d 100644
--- a/copier/tools.py
+++ b/copier/tools.py
@@ -172,6 +172,18 @@ def normalize_str(text: StrOrPath, form: str = "NFD") -> str:
     return unicodedata.normalize(form, str(text))
 
 
+def force_str_end(original_str: str, end: str = "\n") -> str:
+    """Make sure a `original_str` ends with `end`.
+
+    Params:
+        original_str: String that you want to ensure ending.
+        end: String that must exist at the end of `original_str`
+    """
+    if not original_str.endswith(end):
+        return original_str + end
+    return original_str
+
+
 def create_path_filter(patterns: StrOrPathSeq) -> CheckPathFunc:
     """Returns a function that matches a path against given patterns."""
     patterns = [normalize_str(p) for p in patterns]
diff --git a/poetry.lock b/poetry.lock
index 8832ef6ea..a6ef43581 100644
--- a/poetry.lock
+++ b/poetry.lock
@@ -688,13 +688,12 @@ python = "<3.7"
 version = "*"
 
 [[package]]
-category = "dev"
+category = "main"
 description = "Library for building powerful interactive command lines in Python"
-marker = "python_version >= \"3.4\""
 name = "prompt-toolkit"
 optional = false
-python-versions = ">=3.6"
-version = "3.0.3"
+python-versions = ">=3.6.1"
+version = "3.0.6"
 
 [package.dependencies]
 wcwidth = "*"
@@ -1002,9 +1001,8 @@ docs = ["proselint (>=0.10.2)", "sphinx (>=3)", "sphinx-argparse (>=0.2.5)", "sp
 testing = ["coverage (>=5)", "coverage-enable-subprocess (>=1)", "flaky (>=3)", "pytest (>=4)", "pytest-env (>=0.6.2)", "pytest-freezegun (>=0.4.1)", "pytest-mock (>=2)", "pytest-randomly (>=1)", "pytest-timeout (>=1)", "pytest-xdist (>=1.31.0)", "packaging (>=20.0)", "xonsh (>=0.9.16)"]
 
 [[package]]
-category = "dev"
+category = "main"
 description = "Measures the displayed width of unicode strings in a terminal"
-marker = "python_version >= \"3.4\""
 name = "wcwidth"
 optional = false
 python-versions = "*"
@@ -1027,9 +1025,9 @@ testing = ["jaraco.itertools", "func-timeout"]
 docs = ["mkdocstrings", "mkdocs-material", "pymdown-extensions"]
 
 [metadata]
-content-hash = "3e912cd9956127a2e8019fe88e1d20b6643c37a19bffbbcd2df05a1fc7bc3a95"
+content-hash = "6029d208164be0e6295fc8545a7a9a332c9a91ddf7e67ed1ee534fb7c5844eb8"
 lock-version = "1.0"
-python-versions = "^3.6"
+python-versions = "^3.6.1"
 
 [metadata.files]
 apipkg = [
@@ -1323,8 +1321,8 @@ pre-commit = [
     {file = "pre_commit-2.1.1.tar.gz", hash = "sha256:f8d555e31e2051892c7f7b3ad9f620bd2c09271d87e9eedb2ad831737d6211eb"},
 ]
 prompt-toolkit = [
-    {file = "prompt_toolkit-3.0.3-py3-none-any.whl", hash = "sha256:c93e53af97f630f12f5f62a3274e79527936ed466f038953dfa379d4941f651a"},
-    {file = "prompt_toolkit-3.0.3.tar.gz", hash = "sha256:a402e9bf468b63314e37460b68ba68243d55b2f8c4d0192f85a019af3945050e"},
+    {file = "prompt_toolkit-3.0.6-py3-none-any.whl", hash = "sha256:683397077a64cd1f750b71c05afcfc6612a7300cb6932666531e5a54f38ea564"},
+    {file = "prompt_toolkit-3.0.6.tar.gz", hash = "sha256:7630ab85a23302839a0f26b31cc24f518e6155dea1ed395ea61b42c45941b6a6"},
 ]
 ptyprocess = [
     {file = "ptyprocess-0.6.0-py2.py3-none-any.whl", hash = "sha256:d7cc528d76e76342423ca640335bd3633420dc1366f258cb31d05e865ef5ca1f"},
diff --git a/pyproject.toml b/pyproject.toml
index 7920c2d99..97eb311b6 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -26,13 +26,15 @@ copier = "copier.cli:CopierApp.run"
 "Bug Tracker" = "https://github.com/pykong/copier/issues"
 
 [tool.poetry.dependencies]
-python = "^3.6"
+python = "^3.6.1"
 colorama = "^0.4.3"
 jinja2 = "^2.11.2"
 pathspec = "^0.8.0"
 plumbum = "^1.6.9"
+prompt_toolkit = "^3.0.6"
 pydantic = "^1.5.1"
 regex = "^2020.6.8"
+pygments = "^2.6.1"
 pyyaml = "^5.3.1"
 pyyaml-include = "^1.2"
 # packaging is needed when installing from PyPI