diff --git a/docs/docs/comparison.md b/docs/docs/comparison.md
index 6be8d0da..7e06b0ee 100644
--- a/docs/docs/comparison.md
+++ b/docs/docs/comparison.md
@@ -75,3 +75,19 @@ True
 # Compares to now by default
 True
 ```
+
+The `closest()` and `farthest()` methods also work with naive datetimes.
+When the reference datetime is naive, naive candidates remain naive:
+
+```python
+>>> reference = pendulum.naive(2026, 10, 20, 12)
+>>> before = pendulum.naive(2026, 10, 20, 11)
+>>> after = pendulum.naive(2026, 10, 20, 14)
+>>> reference.closest(before, after) == before
+True
+>>> reference.farthest(before, after) == after
+True
+```
+
+As with datetime subtraction, a naive reference cannot be compared with an aware
+candidate. For an aware reference, naive candidates continue to use UTC.
diff --git a/src/pendulum/datetime.py b/src/pendulum/datetime.py
index 96aff25b..45403c4c 100644
--- a/src/pendulum/datetime.py
+++ b/src/pendulum/datetime.py
@@ -499,7 +499,8 @@ def closest(self, *dts: datetime.datetime) -> Self:  # type: ignore[override]
         """
         Get the closest date to the instance.
         """
-        pdts = [self.instance(x) for x in dts]
+        tz = UTC if self.tzinfo is not None else None
+        pdts = [self.instance(x, tz=tz) for x in dts]
 
         return min((abs(self - dt), dt) for dt in pdts)[1]
 
@@ -507,7 +508,8 @@ def farthest(self, *dts: datetime.datetime) -> Self:  # type: ignore[override]
         """
         Get the farthest date from the instance.
         """
-        pdts = [self.instance(x) for x in dts]
+        tz = UTC if self.tzinfo is not None else None
+        pdts = [self.instance(x, tz=tz) for x in dts]
 
         return max((abs(self - dt), dt) for dt in pdts)[1]
 
diff --git a/tests/datetime/test_comparison.py b/tests/datetime/test_comparison.py
index 4e25f0d6..a02ed040 100644
--- a/tests/datetime/test_comparison.py
+++ b/tests/datetime/test_comparison.py
@@ -4,6 +4,8 @@
 
 from datetime import datetime
 
+import pytest
+
 import pendulum
 
 from tests.conftest import assert_datetime
@@ -374,6 +376,106 @@ def test_farthest_with_equals():
     assert farthest == dts[-1]
 
 
+@pytest.mark.parametrize("method", ["closest", "farthest"])
+@pytest.mark.parametrize("native", [False, True])
+@pytest.mark.parametrize("reverse", [False, True])
+def test_closest_and_farthest_with_naive_datetimes(method, native, reverse):
+    instance = pendulum.naive(2026, 10, 20, 12, 34, 56, 123456)
+    near = instance.subtract(microseconds=1)
+    far = instance.add(microseconds=2)
+    candidates = [near, far]
+    if native:
+        candidates = [
+            datetime(
+                dt.year,
+                dt.month,
+                dt.day,
+                dt.hour,
+                dt.minute,
+                dt.second,
+                dt.microsecond,
+            )
+            for dt in candidates
+        ]
+    if reverse:
+        candidates.reverse()
+
+    result = getattr(instance, method)(*candidates)
+
+    assert result == (near if method == "closest" else far)
+    assert type(result) is pendulum.DateTime
+    assert result.tzinfo is None
+
+
+@pytest.mark.parametrize("method", ["closest", "farthest"])
+def test_closest_and_farthest_with_naive_single_candidate(method):
+    instance = pendulum.naive(2026, 10, 20)
+
+    assert getattr(instance, method)(instance) == instance
+
+
+@pytest.mark.parametrize("method", ["closest", "farthest"])
+@pytest.mark.parametrize("reverse", [False, True])
+@pytest.mark.parametrize("tz", [None, "UTC"])
+def test_closest_and_farthest_with_ties(method, reverse, tz):
+    instance = pendulum.datetime(2026, 10, 20, 12, tz=tz)
+    before = instance.subtract(hours=1)
+    after = instance.add(hours=1)
+    candidates = [before, after]
+    if reverse:
+        candidates.reverse()
+
+    result = getattr(instance, method)(*candidates)
+
+    assert result == candidates[0]
+    assert result.tzinfo == instance.tzinfo
+
+
+@pytest.mark.parametrize("method", ["closest", "farthest"])
+def test_closest_and_farthest_with_naive_subclass(method):
+    class CustomDateTime(pendulum.DateTime):
+        pass
+
+    instance = CustomDateTime(2026, 10, 20, 12)
+    candidates = [datetime(2026, 10, 20, 11), datetime(2026, 10, 20, 14)]
+
+    result = getattr(instance, method)(*candidates)
+
+    assert type(result) is CustomDateTime
+    assert result.hour == (11 if method == "closest" else 14)
+    assert result.tzinfo is None
+
+
+@pytest.mark.parametrize("method", ["closest", "farthest"])
+@pytest.mark.parametrize("tz", [None, "UTC", "Europe/Paris"])
+def test_closest_and_farthest_without_candidates(method, tz):
+    instance = pendulum.datetime(2026, 10, 20, tz=tz)
+
+    with pytest.raises(ValueError):
+        getattr(instance, method)()
+
+
+@pytest.mark.parametrize("method", ["closest", "farthest"])
+def test_closest_and_farthest_with_naive_reference_and_aware_candidate(method):
+    instance = pendulum.naive(2026, 10, 20)
+    candidate = pendulum.datetime(2026, 10, 21)
+
+    with pytest.raises(TypeError, match="offset-naive and offset-aware"):
+        getattr(instance, method)(candidate)
+
+
+@pytest.mark.parametrize("method", ["closest", "farthest"])
+def test_closest_and_farthest_aware_reference_keeps_naive_candidate_default(method):
+    instance = pendulum.datetime(2026, 10, 20, 12, tz="Europe/Paris")
+    naive = datetime(2026, 10, 20, 10)
+    aware = pendulum.datetime(2026, 10, 20, 13, tz="Europe/Paris")
+
+    result = getattr(instance, method)(naive, aware)
+
+    assert result == (pendulum.instance(naive) if method == "closest" else aware)
+    assert result.timezone_name == ("UTC" if method == "closest" else "Europe/Paris")
+
+
 def test_is_same_day():
     dt1 = pendulum.datetime(2015, 5, 28, 12, 0, 0)
     dt2 = pendulum.datetime(2015, 5, 29, 12, 0, 0)