diff --git a/README.md b/README.md
index 592b12e75a..218d86cf0b 100644
--- a/README.md
+++ b/README.md
@@ -148,9 +148,9 @@ print(sqlglot.transpile(sql, read='mysql', pretty=True)[0])
 */
 SELECT
   tbl.cola /* comment 1 */ + tbl.colb /* comment 2 */,
-  CAST(x AS INT), -- comment 3
-  y -- comment 4
-FROM bar /* comment 5 */, tbl /*          comment 6*/
+  CAST(x AS INT), /* comment 3 */
+  y /* comment 4 */
+FROM bar /* comment 5 */, tbl /*          comment 6 */
 ```
 
 
diff --git a/sqlglot/expressions.py b/sqlglot/expressions.py
index ae26db945b..81e36a88f0 100644
--- a/sqlglot/expressions.py
+++ b/sqlglot/expressions.py
@@ -43,14 +43,14 @@ class Expression(metaclass=_Expression):
 
     key = "Expression"
     arg_types = {"this": True}
-    __slots__ = ("args", "parent", "arg_key", "type", "comment")
+    __slots__ = ("args", "parent", "arg_key", "type", "comments")
 
     def __init__(self, **args):
         self.args = args
         self.parent = None
         self.arg_key = None
         self.type = None
-        self.comment = None
+        self.comments = None
 
         for arg_key, value in self.args.items():
             self._set_parent(arg_key, value)
@@ -88,19 +88,6 @@ def text(self, key):
             return field.this
         return ""
 
-    def find_comment(self, key: str) -> str:
-        """
-        Finds the comment that is attached to a specified child node.
-
-        Args:
-            key: the key of the target child node (e.g. "this", "expression", etc).
-
-        Returns:
-            The comment attached to the child node, or the empty string, if it doesn't exist.
-        """
-        field = self.args.get(key)
-        return field.comment if isinstance(field, Expression) else ""
-
     @property
     def is_string(self):
         return isinstance(self, Literal) and self.args["is_string"]
@@ -137,7 +124,7 @@ def alias_or_name(self):
 
     def __deepcopy__(self, memo):
         copy = self.__class__(**deepcopy(self.args))
-        copy.comment = self.comment
+        copy.comments = self.comments
         copy.type = self.type
         return copy
 
@@ -369,7 +356,7 @@ def to_s(self, hide_missing: bool = True, level: int = 0) -> str:
             )
             for k, vs in self.args.items()
         }
-        args["comment"] = self.comment
+        args["comments"] = self.comments
         args["type"] = self.type
         args = {k: v for k, v in args.items() if v or not hide_missing}
 
diff --git a/sqlglot/generator.py b/sqlglot/generator.py
index 156e6abfcb..2792dada09 100644
--- a/sqlglot/generator.py
+++ b/sqlglot/generator.py
@@ -1,7 +1,6 @@
 from __future__ import annotations
 
 import logging
-import re
 import typing as t
 
 from sqlglot import exp
@@ -12,8 +11,6 @@
 
 logger = logging.getLogger("sqlglot")
 
-NEWLINE_RE = re.compile("\r\n?|\n")
-
 
 class Generator:
     """
@@ -226,25 +223,24 @@ def sep(self, sep=" "):
     def seg(self, sql, sep=" "):
         return f"{self.sep(sep)}{sql}"
 
-    def maybe_comment(self, sql, expression, single_line=False):
-        comment = expression.comment if self._comments else None
-
-        if not comment:
-            return sql
-
+    def pad_comment(self, comment):
         comment = " " + comment if comment[0].strip() else comment
         comment = comment + " " if comment[-1].strip() else comment
+        return comment
 
-        if isinstance(expression, self.WITH_SEPARATED_COMMENTS):
-            return f"/*{comment}*/{self.sep()}{sql}"
+    def maybe_comment(self, sql, expression):
+        comments = expression.comments if self._comments else None
 
-        if not self.pretty:
-            return f"{sql} /*{comment}*/"
+        if not comments:
+            return sql
 
-        if not NEWLINE_RE.search(comment):
-            return f"{sql} --{comment.rstrip()}" if single_line else f"{sql} /*{comment}*/"
+        sep = "\n" if self.pretty else " "
+        comments = sep.join(f"/*{self.pad_comment(comment)}*/" for comment in comments)
+
+        if isinstance(expression, self.WITH_SEPARATED_COMMENTS):
+            return f"{comments}{self.sep()}{sql}"
 
-        return f"/*{comment}*/\n{sql}" if sql else f" /*{comment}*/"
+        return f"{sql} {comments}"
 
     def wrap(self, expression):
         this_sql = self.indent(
@@ -1337,15 +1333,15 @@ def expressions(self, expression, key=None, flat=False, indent=True, sep=", "):
         result_sqls = []
         for i, e in enumerate(expressions):
             sql = self.sql(e, comment=False)
-            comment = self.maybe_comment("", e, single_line=True)
+            comments = self.maybe_comment("", e)
 
             if self.pretty:
                 if self._leading_comma:
-                    result_sqls.append(f"{sep if i > 0 else pad}{sql}{comment}")
+                    result_sqls.append(f"{sep if i > 0 else pad}{sql}{comments}")
                 else:
-                    result_sqls.append(f"{sql}{stripped_sep if i + 1 < num_sqls else ''}{comment}")
+                    result_sqls.append(f"{sql}{stripped_sep if i + 1 < num_sqls else ''}{comments}")
             else:
-                result_sqls.append(f"{sql}{comment}{sep if i + 1 < num_sqls else ''}")
+                result_sqls.append(f"{sql}{comments}{sep if i + 1 < num_sqls else ''}")
 
         result_sqls = "\n".join(result_sqls) if self.pretty else "".join(result_sqls)
         return self.indent(result_sqls, skip_first=False) if indent else result_sqls
diff --git a/sqlglot/parser.py b/sqlglot/parser.py
index c480a1196a..0656b5f534 100644
--- a/sqlglot/parser.py
+++ b/sqlglot/parser.py
@@ -567,7 +567,7 @@ class Parser(metaclass=_Parser):
         "_curr",
         "_next",
         "_prev",
-        "_prev_comment",
+        "_prev_comments",
         "_show_trie",
         "_set_trie",
     )
@@ -600,7 +600,7 @@ def reset(self):
         self._curr = None
         self._next = None
         self._prev = None
-        self._prev_comment = None
+        self._prev_comments = None
 
     def parse(self, raw_tokens, sql=None):
         """
@@ -694,9 +694,9 @@ def raise_error(self, message, token=None):
 
     def expression(self, exp_class, **kwargs):
         instance = exp_class(**kwargs)
-        if self._prev_comment:
-            instance.comment = self._prev_comment
-            self._prev_comment = None
+        if self._prev_comments:
+            instance.comments = self._prev_comments
+            self._prev_comments = None
         self.validate_expression(instance)
         return instance
 
@@ -739,10 +739,10 @@ def _advance(self, times=1):
         self._next = seq_get(self._tokens, self._index + 1)
         if self._index > 0:
             self._prev = self._tokens[self._index - 1]
-            self._prev_comment = self._prev.comment
+            self._prev_comments = self._prev.comments
         else:
             self._prev = None
-            self._prev_comment = None
+            self._prev_comments = None
 
     def _retreat(self, index):
         self._advance(index - self._index)
@@ -1088,7 +1088,7 @@ def _parse_select(self, nested=False, table=False):
                 self.raise_error(f"{this.key} does not support CTE")
                 this = cte
         elif self._match(TokenType.SELECT):
-            comment = self._prev_comment
+            comments = self._prev_comments
 
             hint = self._parse_hint()
             all_ = self._match(TokenType.ALL)
@@ -1113,7 +1113,7 @@ def _parse_select(self, nested=False, table=False):
                 expressions=expressions,
                 limit=limit,
             )
-            this.comment = comment
+            this.comments = comments
             from_ = self._parse_from()
             if from_:
                 this.set("from", from_)
@@ -1872,7 +1872,7 @@ def _parse_primary(self):
             return exp.Literal.number(f"0.{self._prev.text}")
 
         if self._match(TokenType.L_PAREN):
-            comment = self._prev_comment
+            comments = self._prev_comments
             query = self._parse_select()
 
             if query:
@@ -1892,8 +1892,8 @@ def _parse_primary(self):
                 this = self.expression(exp.Tuple, expressions=expressions)
             else:
                 this = self.expression(exp.Paren, this=this)
-            if comment:
-                this.comment = comment
+            if comments:
+                this.comments = comments
             return this
 
         return None
@@ -2160,7 +2160,7 @@ def _parse_bracket(self, this):
         if not self._match(TokenType.R_BRACKET):
             self.raise_error("Expected ]")
 
-        this.comment = self._prev_comment
+        this.comments = self._prev_comments
         return self._parse_bracket(this)
 
     def _parse_case(self):
@@ -2482,8 +2482,8 @@ def _parse_csv(self, parse_method, sep=TokenType.COMMA):
         items = [parse_result] if parse_result is not None else []
 
         while self._match(sep):
-            if parse_result and self._prev_comment is not None:
-                parse_result.comment = self._prev_comment
+            if parse_result and self._prev_comments:
+                parse_result.comments = self._prev_comments
 
             parse_result = parse_method()
             if parse_result is not None:
@@ -2622,14 +2622,14 @@ def _match_pair(self, token_type_a, token_type_b, advance=True):
     def _match_l_paren(self, expression=None):
         if not self._match(TokenType.L_PAREN):
             self.raise_error("Expecting (")
-        if expression and self._prev_comment:
-            expression.comment = self._prev_comment
+        if expression and self._prev_comments:
+            expression.comments = self._prev_comments
 
     def _match_r_paren(self, expression=None):
         if not self._match(TokenType.R_PAREN):
             self.raise_error("Expecting )")
-        if expression and self._prev_comment:
-            expression.comment = self._prev_comment
+        if expression and self._prev_comments:
+            expression.comments = self._prev_comments
 
     def _match_texts(self, texts):
         if self._curr and self._curr.text.upper() in texts:
diff --git a/sqlglot/tokens.py b/sqlglot/tokens.py
index fa006268a5..dda0e012b6 100644
--- a/sqlglot/tokens.py
+++ b/sqlglot/tokens.py
@@ -294,7 +294,7 @@ class TokenType(AutoName):
 
 
 class Token:
-    __slots__ = ("token_type", "text", "line", "col", "comment")
+    __slots__ = ("token_type", "text", "line", "col", "comments")
 
     @classmethod
     def number(cls, number: int) -> Token:
@@ -322,13 +322,13 @@ def __init__(
         text: str,
         line: int = 1,
         col: int = 1,
-        comment: t.Optional[str] = None,
+        comments: t.List[str] = [],
     ) -> None:
         self.token_type = token_type
         self.text = text
         self.line = line
         self.col = max(col - len(text), 1)
-        self.comment = comment
+        self.comments = comments
 
     def __repr__(self) -> str:
         attributes = ", ".join(f"{k}: {getattr(self, k)}" for k in self.__slots__)
@@ -690,12 +690,12 @@ class Tokenizer(metaclass=_Tokenizer):
         "_current",
         "_line",
         "_col",
-        "_comment",
+        "_comments",
         "_char",
         "_end",
         "_peek",
         "_prev_token_line",
-        "_prev_token_comment",
+        "_prev_token_comments",
         "_prev_token_type",
         "_replace_backslash",
     )
@@ -712,13 +712,13 @@ def reset(self) -> None:
         self._current = 0
         self._line = 1
         self._col = 1
-        self._comment = None
+        self._comments: t.List[str] = []
 
         self._char = None
         self._end = None
         self._peek = None
         self._prev_token_line = -1
-        self._prev_token_comment = None
+        self._prev_token_comments: t.List[str] = []
         self._prev_token_type = None
 
     def tokenize(self, sql: str) -> t.List[Token]:
@@ -771,7 +771,7 @@ def _text(self) -> str:
 
     def _add(self, token_type: TokenType, text: t.Optional[str] = None) -> None:
         self._prev_token_line = self._line
-        self._prev_token_comment = self._comment
+        self._prev_token_comments = self._comments
         self._prev_token_type = token_type  # type: ignore
         self.tokens.append(
             Token(
@@ -779,10 +779,10 @@ def _add(self, token_type: TokenType, text: t.Optional[str] = None) -> None:
                 self._text if text is None else text,
                 self._line,
                 self._col,
-                self._comment,
+                self._comments,
             )
         )
-        self._comment = None
+        self._comments = []
 
         if token_type in self.COMMANDS and (
             len(self.tokens) == 1 or self.tokens[-2].token_type == TokenType.SEMICOLON
@@ -861,22 +861,18 @@ def _scan_comment(self, comment_start: str) -> bool:
             while not self._end and self._chars(comment_end_size) != comment_end:
                 self._advance()
 
-            self._comment = self._text[comment_start_size : -comment_end_size + 1]  # type: ignore
+            self._comments.append(self._text[comment_start_size : -comment_end_size + 1])  # type: ignore
             self._advance(comment_end_size - 1)
         else:
             while not self._end and self.WHITE_SPACE.get(self._peek) != TokenType.BREAK:  # type: ignore
                 self._advance()
-            self._comment = self._text[comment_start_size:]  # type: ignore
-
-        # Leading comment is attached to the succeeding token, whilst trailing comment to the preceding. If both
-        # types of comment can be attached to a token, the trailing one is discarded in favour of the leading one.
+            self._comments.append(self._text[comment_start_size:])  # type: ignore
 
+        # Leading comment is attached to the succeeding token, whilst trailing comment to the preceding.
+        # Multiple consecutive comments are preserved by appending them to the current comments list.
         if comment_start_line == self._prev_token_line:
-            if self._prev_token_comment is None:
-                self.tokens[-1].comment = self._comment
-                self._prev_token_comment = self._comment
-
-            self._comment = None
+            self.tokens[-1].comments.extend(self._comments)
+            self._comments = []
 
         return True
 
diff --git a/tests/dialects/test_dialect.py b/tests/dialects/test_dialect.py
index 09acc42326..6033570511 100644
--- a/tests/dialects/test_dialect.py
+++ b/tests/dialects/test_dialect.py
@@ -1270,8 +1270,8 @@ def test_hash_comments(self):
         self.validate_all(
             """/* comment1 */
 SELECT
-  x, -- comment2
-  y -- comment3""",
+  x, /* comment2 */
+  y /* comment3 */""",
             read={
                 "mysql": """SELECT # comment1
   x, # comment2
diff --git a/tests/fixtures/identity.sql b/tests/fixtures/identity.sql
index 79fcfabddb..e162d1dfc9 100644
--- a/tests/fixtures/identity.sql
+++ b/tests/fixtures/identity.sql
@@ -581,6 +581,7 @@ SELECT * FROM (tbl1 JOIN (tbl2 JOIN tbl3) ON bla = foo)
 SELECT * FROM (tbl1 JOIN LATERAL (SELECT * FROM bla) AS tbl)
 SELECT CAST(x AS INT) /* comment */ FROM foo
 SELECT a /* x */, b /* x */
+SELECT a /* x */ /* y */ /* z */, b /* k */ /* m */
 SELECT * FROM foo /* x */, bla /* x */
 SELECT 1 /* comment */ + 1
 SELECT 1 /* c1 */ + 2 /* c2 */
diff --git a/tests/test_expressions.py b/tests/test_expressions.py
index 5f9023d3b6..0e13adeb64 100644
--- a/tests/test_expressions.py
+++ b/tests/test_expressions.py
@@ -599,9 +599,9 @@ def test_comment_alias(self):
             """SELECT
   a,
   b AS B,
-  c, -- comment
-  d AS D, -- another comment
-  CAST(x AS INT) -- final comment
+  c, /* comment */
+  d AS D, /* another comment */
+  CAST(x AS INT) /* final comment */
 FROM foo""",
         )
 
diff --git a/tests/test_parser.py b/tests/test_parser.py
index 68cbf19361..fa7b589ad9 100644
--- a/tests/test_parser.py
+++ b/tests/test_parser.py
@@ -205,8 +205,9 @@ def test_var(self):
     def test_comments(self):
         expression = parse_one(
             """
-            --comment1
-            SELECT /* this won't be used */
+            --comment1.1
+            --comment1.2
+            SELECT /*comment1.3*/
                 a, --comment2
                 b as B, --comment3:testing
                 "test--annotation",
@@ -217,13 +218,13 @@ def test_comments(self):
         """
         )
 
-        self.assertEqual(expression.comment, "comment1")
-        self.assertEqual(expression.expressions[0].comment, "comment2")
-        self.assertEqual(expression.expressions[1].comment, "comment3:testing")
-        self.assertEqual(expression.expressions[2].comment, None)
-        self.assertEqual(expression.expressions[3].comment, "comment4 --foo")
-        self.assertEqual(expression.expressions[4].comment, "")
-        self.assertEqual(expression.expressions[5].comment, " space")
+        self.assertEqual(expression.comments, ["comment1.1", "comment1.2", "comment1.3"])
+        self.assertEqual(expression.expressions[0].comments, ["comment2"])
+        self.assertEqual(expression.expressions[1].comments, ["comment3:testing"])
+        self.assertEqual(expression.expressions[2].comments, None)
+        self.assertEqual(expression.expressions[3].comments, ["comment4 --foo"])
+        self.assertEqual(expression.expressions[4].comments, [""])
+        self.assertEqual(expression.expressions[5].comments, [" space"])
 
     def test_type_literals(self):
         self.assertEqual(parse_one("int 1"), parse_one("CAST(1 AS INT)"))
diff --git a/tests/test_tokens.py b/tests/test_tokens.py
index d4772ba9e3..1d1b966566 100644
--- a/tests/test_tokens.py
+++ b/tests/test_tokens.py
@@ -7,13 +7,13 @@ class TestTokens(unittest.TestCase):
     def test_comment_attachment(self):
         tokenizer = Tokenizer()
         sql_comment = [
-            ("/*comment*/ foo", "comment"),
-            ("/*comment*/ foo --test", "comment"),
-            ("--comment\nfoo --test", "comment"),
-            ("foo --comment", "comment"),
-            ("foo", None),
-            ("foo /*comment 1*/ /*comment 2*/", "comment 1"),
+            ("/*comment*/ foo", ["comment"]),
+            ("/*comment*/ foo --test", ["comment", "test"]),
+            ("--comment\nfoo --test", ["comment", "test"]),
+            ("foo --comment", ["comment"]),
+            ("foo", []),
+            ("foo /*comment 1*/ /*comment 2*/", ["comment 1", "comment 2"]),
         ]
 
         for sql, comment in sql_comment:
-            self.assertEqual(tokenizer.tokenize(sql)[0].comment, comment)
+            self.assertEqual(tokenizer.tokenize(sql)[0].comments, comment)
diff --git a/tests/test_transpile.py b/tests/test_transpile.py
index fb8546054a..7bf53e5fef 100644
--- a/tests/test_transpile.py
+++ b/tests/test_transpile.py
@@ -64,7 +64,7 @@ def test_leading_comma(self):
         )
         self.validate(
             "SELECT FOO, /*x*/\nBAR, /*y*/\nBAZ",
-            "SELECT\n    FOO -- x\n  , BAR -- y\n  , BAZ",
+            "SELECT\n    FOO /* x */\n  , BAR /* y */\n  , BAZ",
             leading_comma=True,
             pretty=True,
         )
@@ -84,7 +84,8 @@ def test_space(self):
     def test_comments(self):
         self.validate("SELECT */*comment*/", "SELECT * /* comment */")
         self.validate(
-            "SELECT * FROM table /*comment 1*/ /*comment 2*/", "SELECT * FROM table /* comment 1 */"
+            "SELECT * FROM table /*comment 1*/ /*comment 2*/",
+            "SELECT * FROM table /* comment 1 */ /* comment 2 */",
         )
         self.validate("SELECT 1 FROM foo -- comment", "SELECT 1 FROM foo /* comment */")
         self.validate("SELECT --+5\nx FROM foo", "/* +5 */ SELECT x FROM foo")
@@ -118,6 +119,53 @@ def test_comments(self):
         )
         self.validate(
             """
+-- comment 1
+-- comment 2
+-- comment 3
+SELECT * FROM foo
+            """,
+            "/* comment 1 */ /* comment 2 */ /* comment 3 */ SELECT * FROM foo",
+        )
+        self.validate(
+            """
+-- comment 1
+-- comment 2
+-- comment 3
+SELECT * FROM foo""",
+            """/* comment 1 */
+/* comment 2 */
+/* comment 3 */
+SELECT
+  *
+FROM foo""",
+            pretty=True,
+        )
+        self.validate(
+            """
+SELECT * FROM tbl /*line1
+line2
+line3*/ /*another comment*/ where 1=1 -- comment at the end""",
+            """SELECT * FROM tbl /* line1
+line2
+line3 */ /* another comment */ WHERE 1 = 1 /* comment at the end */""",
+        )
+        self.validate(
+            """
+SELECT * FROM tbl /*line1
+line2
+line3*/ /*another comment*/ where 1=1 -- comment at the end""",
+            """SELECT
+  *
+FROM tbl /* line1
+line2
+line3 */
+/* another comment */
+WHERE
+  1 = 1 /* comment at the end */""",
+            pretty=True,
+        )
+        self.validate(
+            """
             /* multi
                line
                comment
@@ -136,8 +184,8 @@ def test_comments(self):
             */
 SELECT
   tbl.cola /* comment 1 */ + tbl.colb /* comment 2 */,
-  CAST(x AS INT), -- comment 3
-  y -- comment 4
+  CAST(x AS INT), /* comment 3 */
+  y /* comment 4 */
 FROM bar /* comment 5 */, tbl /*          comment 6 */""",
             read="mysql",
             pretty=True,