diff --git a/Lib/ast.py b/Lib/ast.py
index d8bd337..7275fe2 100644
--- a/Lib/ast.py
+++ b/Lib/ast.py
@@ -662,17 +662,23 @@ def next(self):
         except ValueError:
             return self
 
+
+_SINGLE_QUOTES = ("'", '"')
+_MULTI_QUOTES = ('"""', "'''")
+_ALL_QUOTES = (*_SINGLE_QUOTES, *_MULTI_QUOTES)
+
 class _Unparser(NodeVisitor):
     """Methods in this class recursively traverse an AST and
     output source code for the abstract syntax; original formatting
     is disregarded."""
 
-    def __init__(self):
+    def __init__(self, *, _avoid_backslashes=False):
         self._source = []
         self._buffer = []
         self._precedences = {}
         self._type_ignores = {}
         self._indent = 0
+        self._avoid_backslashes = _avoid_backslashes
 
     def interleave(self, inter, f, seq):
         """Call f on each item in seq, calling inter() in between."""
@@ -1067,15 +1073,85 @@ def visit_AsyncWith(self, node):
         with self.block(extra=self.get_type_comment(node)):
             self.traverse(node.body)
 
+    def _str_literal_helper(
+        self, string, *, quote_types=_ALL_QUOTES, escape_special_whitespace=False
+    ):
+        """Helper for writing string literals, minimizing escapes.
+        Returns the tuple (string literal to write, possible quote types).
+        """
+        def escape_char(c):
+            # \n and \t are non-printable, but we only escape them if
+            # escape_special_whitespace is True
+            if not escape_special_whitespace and c in "\n\t":
+                return c
+            # Always escape backslashes and other non-printable characters
+            if c == "\\" or not c.isprintable():
+                return c.encode("unicode_escape").decode("ascii")
+            return c
+
+        escaped_string = "".join(map(escape_char, string))
+        possible_quotes = quote_types
+        if "\n" in escaped_string:
+            possible_quotes = [q for q in possible_quotes if q in _MULTI_QUOTES]
+        possible_quotes = [q for q in possible_quotes if q not in escaped_string]
+        if not possible_quotes:
+            # If there aren't any possible_quotes, fallback to using repr
+            # on the original string. Try to use a quote from quote_types,
+            # e.g., so that we use triple quotes for docstrings.
+            string = repr(string)
+            quote = next((q for q in quote_types if string[0] in q), string[0])
+            return string[1:-1], [quote]
+        if escaped_string:
+            # Sort so that we prefer '''"''' over """\""""
+            possible_quotes.sort(key=lambda q: q[0] == escaped_string[-1])
+            # If we're using triple quotes and we'd need to escape a final
+            # quote, escape it
+            if possible_quotes[0][0] == escaped_string[-1]:
+                assert len(possible_quotes[0]) == 3
+                escaped_string = escaped_string[:-1] + "\\" + escaped_string[-1]
+        return escaped_string, possible_quotes
+
+    def _write_str_avoiding_backslashes(self, string, *, quote_types=_ALL_QUOTES):
+        """Write string literal value with a best effort attempt to avoid backslashes."""
+        string, quote_types = self._str_literal_helper(string, quote_types=quote_types)
+        quote_type = quote_types[0]
+        self.write(f"{quote_type}{string}{quote_type}")
+
     def visit_JoinedStr(self, node):
         self.write("f")
-        self._fstring_JoinedStr(node, self.buffer_writer)
-        self.write(repr(self.buffer))
+        if self._avoid_backslashes:
+            self._fstring_JoinedStr(node, self.buffer_writer)
+            self._write_str_avoiding_backslashes(self.buffer)
+            return
+
+        # If we don't need to avoid backslashes globally (i.e., we only need
+        # to avoid them inside FormattedValues), it's cosmetically preferred
+        # to use escaped whitespace. That is, it's preferred to use backslashes
+        # for cases like: f"{x}\n". To accomplish this, we keep track of what
+        # in our buffer corresponds to FormattedValues and what corresponds to
+        # Constant parts of the f-string, and allow escapes accordingly.
+        buffer = []
+        for value in node.values:
+            meth = getattr(self, "_fstring_" + type(value).__name__)
+            meth(value, self.buffer_writer)
+            buffer.append((self.buffer, isinstance(value, Constant)))
+        new_buffer = []
+        quote_types = _ALL_QUOTES
+        for value, is_constant in buffer:
+            # Repeatedly narrow down the list of possible quote_types
+            value, quote_types = self._str_literal_helper(
+                value, quote_types=quote_types,
+                escape_special_whitespace=is_constant
+            )
+            new_buffer.append(value)
+        value = "".join(new_buffer)
+        quote_type = quote_types[0]
+        self.write(f"{quote_type}{value}{quote_type}")
 
     def visit_FormattedValue(self, node):
         self.write("f")
         self._fstring_FormattedValue(node, self.buffer_writer)
-        self.write(repr(self.buffer))
+        self._write_str_avoiding_backslashes(self.buffer)
 
     def _fstring_JoinedStr(self, node, write):
         for value in node.values:
@@ -1090,11 +1166,13 @@ def _fstring_Constant(self, node, write):
 
     def _fstring_FormattedValue(self, node, write):
         write("{")
-        unparser = type(self)()
+        unparser = type(self)(_avoid_backslashes=True)
         unparser.set_precedence(_Precedence.TEST.next(), node.value)
         expr = unparser.visit(node.value)
         if expr.startswith("{"):
             write(" ")  # Separate pair of opening brackets as "{ {"
+        if "\\" in expr:
+            raise ValueError("Unable to avoid backslash in f-string expression part")
         write(expr)
         if node.conversion != -1:
             conversion = chr(node.conversion)
@@ -1111,33 +1189,17 @@ def visit_Name(self, node):
         self.write(node.id)
 
     def _write_docstring(self, node):
-        def esc_char(c):
-            if c in ("\n", "\t"):
-                # In the AST form, we don't know the author's intentation
-                # about how this should be displayed. We'll only escape
-                # \n and \t, because they are more likely to be unescaped
-                # in the source
-                return c
-            return c.encode('unicode_escape').decode('ascii')
-
         self.fill()
         if node.kind == "u":
             self.write("u")
-
-        value = node.value
-        if value:
-            # Preserve quotes in the docstring by escaping them
-            value = "".join(map(esc_char, value))
-            if value[-1] == '"':
-                value = value.replace('"', '\\"', -1)
-            value = value.replace('"""', '""\\"')
-
-        self.write(f'"""{value}"""')
+        self._write_str_avoiding_backslashes(node.value, quote_types=_MULTI_QUOTES)
 
     def _write_constant(self, value):
         if isinstance(value, (float, complex)):
             # Substitute overflowing decimal literal for AST infinities.
             self.write(repr(value).replace("inf", _INFSTR))
+        elif self._avoid_backslashes and isinstance(value, str):
+            self._write_str_avoiding_backslashes(value)
         else:
             self.write(repr(value))
 
diff --git a/Lib/test/test_unparse.py b/Lib/test/test_unparse.py
index 532aa3a..c7c8613 100644
--- a/Lib/test/test_unparse.py
+++ b/Lib/test/test_unparse.py
@@ -152,6 +152,18 @@ def test_fstrings(self):
         # See issue 25180
         self.check_ast_roundtrip(r"""f'{f"{0}"*3}'""")
         self.check_ast_roundtrip(r"""f'{f"{y}"*3}'""")
+        self.check_ast_roundtrip("""f''""")
+        self.check_ast_roundtrip('''f"""'end' "quote\\""""''')
+
+    def test_fstrings_complicated(self):
+        # See issue 28002
+        self.check_ast_roundtrip("""f'''{"'"}'''""")
+        self.check_ast_roundtrip('''f\'\'\'-{f"""*{f"+{f'.{x}.'}+"}*"""}-\'\'\'''')
+        self.check_ast_roundtrip('''f\'\'\'-{f"""*{f"+{f'.{x}.'}+"}*"""}-'single quote\\'\'\'\'''')
+        self.check_ast_roundtrip('f"""{\'\'\'\n\'\'\'}"""')
+        self.check_ast_roundtrip('f"""{g(\'\'\'\n\'\'\')}"""')
+        self.check_ast_roundtrip('''f"a\\r\\nb"''')
+        self.check_ast_roundtrip('''f"\\u2028{'x'}"''')
 
     def test_strings(self):
         self.check_ast_roundtrip("u'foo'")
@@ -311,6 +323,9 @@ def test_invalid_fstring_conversion(self):
             )
         )
 
+    def test_invalid_fstring_backslash(self):
+        self.check_invalid(ast.FormattedValue(value=ast.Constant(value="\\\\")))
+
     def test_invalid_set(self):
         self.check_invalid(ast.Set(elts=[]))
 
@@ -330,8 +345,8 @@ def test_docstrings(self):
             '\r\\r\t\\t\n\\n',
             '""">>> content = \"\"\"blabla\"\"\" <<<"""',
             r'foo\n\x00',
-            '🐍⛎𩸽üéş^\N{LONG RIGHTWARDS SQUIGGLE ARROW}'
-
+            "' \\'\\'\\'\"\"\" \"\"\\'\\' \\'",
+            '🐍⛎𩸽üéş^\\\\X\\\\BB\N{LONG RIGHTWARDS SQUIGGLE ARROW}'
         )
         for docstring in docstrings:
             # check as Module docstrings for easy testing
@@ -416,7 +431,6 @@ def test_simple_expressions_parens(self):
         self.check_src_roundtrip("call((yield x))")
         self.check_src_roundtrip("return x + (yield x)")
 
-
     def test_class_bases_and_keywords(self):
         self.check_src_roundtrip("class X:\n    pass")
         self.check_src_roundtrip("class X(A):\n    pass")
@@ -429,6 +443,13 @@ def test_class_bases_and_keywords(self):
         self.check_src_roundtrip("class X(*args):\n    pass")
         self.check_src_roundtrip("class X(*args, **kwargs):\n    pass")
 
+    def test_fstrings(self):
+        self.check_src_roundtrip('''f\'\'\'-{f"""*{f"+{f'.{x}.'}+"}*"""}-\'\'\'''')
+        self.check_src_roundtrip('''f"\\u2028{'x'}"''')
+        self.check_src_roundtrip(r"f'{x}\n'")
+        self.check_src_roundtrip('''f''\'{"""\n"""}\\n''\'''')
+        self.check_src_roundtrip('''f''\'{f"""{x}\n"""}\\n''\'''')
+
     def test_docstrings(self):
         docstrings = (
             '"""simple doc string"""',
@@ -443,6 +464,10 @@ def test_docstrings(self):
             '""""""',
             '"""\'\'\'"""',
             '"""\'\'\'\'\'\'"""',
+            '"""🐍⛎𩸽üéş^\\\\X\\\\BB⟿"""',
+            '"""end in single \'quote\'"""',
+            "'''end in double \"quote\"'''",
+            '"""almost end in double "quote"."""',
         )
 
         for prefix in docstring_prefixes:
@@ -483,9 +508,8 @@ class DirectoryTestCase(ASTTestCase):
 
     lib_dir = pathlib.Path(__file__).parent / ".."
     test_directories = (lib_dir, lib_dir / "test")
-    skip_files = {"test_fstring.py"}
     run_always_files = {"test_grammar.py", "test_syntax.py", "test_compile.py",
-                        "test_ast.py", "test_asdl_parser.py"}
+                        "test_ast.py", "test_asdl_parser.py", "test_fstring.py"}
 
     _files_to_test = None
 
@@ -525,14 +549,6 @@ def test_files(self):
             if test.support.verbose:
                 print(f"Testing {item.absolute()}")
 
-            # Some f-strings are not correctly round-tripped by
-            # Tools/parser/unparse.py.  See issue 28002 for details.
-            # We need to skip files that contain such f-strings.
-            if item.name in self.skip_files:
-                if test.support.verbose:
-                    print(f"Skipping {item.absolute()}: see issue 28002")
-                continue
-
             with self.subTest(filename=item):
                 source = read_pyfile(item)
                 self.check_ast_roundtrip(source)