diff --git a/rich/pretty.py b/rich/pretty.py
index 12ed02a6..1ed1df14 100644
--- a/rich/pretty.py
+++ b/rich/pretty.py
@@ -141,6 +141,7 @@ class Pretty:
         max_string (int, optional): Maximum length of string before truncating, or None to disable. Defaults to None.
         expand_all (bool, optional): Expand all containers. Defaults to False.
         margin (int, optional): Subtrace a margin from width to force containers to expand earlier. Defaults to 0.
+        insert_line (bool, optional): Insert a new line if the output has multiple new lines. Defaults to False.
     """
 
     def __init__(
@@ -157,6 +158,7 @@ class Pretty:
         max_string: int = None,
         expand_all: bool = False,
         margin: int = 0,
+        insert_line: bool = False,
     ) -> None:
         self._object = _object
         self.highlighter = highlighter or ReprHighlighter()
@@ -169,6 +171,7 @@ class Pretty:
         self.max_string = max_string
         self.expand_all = expand_all
         self.margin = margin
+        self.insert_line = insert_line
 
     def __rich_console__(
         self, console: "Console", options: "ConsoleOptions"
@@ -193,6 +196,8 @@ class Pretty:
             pretty_text = pretty_text.with_indent_guides(
                 self.indent_size, style="repr.indent"
             )
+        if self.insert_line and "\n" in pretty_text:
+            yield ""
         yield pretty_text
 
     def __rich_measure__(self, console: "Console", max_width: int) -> "Measurement":
diff --git a/tests/test_pretty.py b/tests/test_pretty.py
index aa540413..4ba8c279 100644
--- a/tests/test_pretty.py
+++ b/tests/test_pretty.py
@@ -134,3 +134,12 @@ def test_tuples():
     print(repr(result))
     expected = "(1,)\n(\n│   1,\n)\n(\n│   (\n│   │   1,\n│   ),\n)\n"
     assert result == expected
+
+
+def test_newline():
+    console = Console(color_system=None)
+    console.begin_capture()
+    console.print(Pretty((1,), insert_line=True, expand_all=True))
+    result = console.end_capture()
+    expected = "\n(\n    1,\n)\n"
+    assert result == expected