diff --git a/tests/test_datetime.py b/tests/test_datetime.py
index 76cdf80..f31a7cf 100644
--- a/tests/test_datetime.py
+++ b/tests/test_datetime.py
@@ -775,7 +775,7 @@ def test_happy_strings(self):
             {"id": 6, "date": "2022-06-15"},
             {"id": 7, "date": "foobar"},
         ]
-        result = group_by_year_and_month({"items": input_data}, "date")
+        result = group_by_year_and_month(input_data, "date")
         expected = [
             {
                 "heading": "2021",
@@ -828,7 +828,7 @@ def test_happy_datetime(self):
             {"id": 6, "date": datetime.date(2022, 6, 15)},
             {"id": 7, "date": None},
         ]
-        result = group_by_year_and_month({"items": input_data}, "date")
+        result = group_by_year_and_month(input_data, "date")
         expected = [
             {
                 "heading": "2021",
@@ -882,7 +882,7 @@ def test_happy_strings_reverse(self):
             {"id": 6, "date": "2022-06-15"},
             {"id": 7, "date": "foobar"},
         ]
-        result = group_by_year_and_month({"items": input_data}, "date", reverse=True)
+        result = group_by_year_and_month(input_data, "date", reverse=True)
         expected = [
             {
                 "heading": "2022",
@@ -935,7 +935,7 @@ def test_happy_datetime_reverse(self):
             {"id": 6, "date": datetime.date(2022, 6, 15)},
             {"id": 7, "date": None},
         ]
-        result = group_by_year_and_month({"items": input_data}, "date", reverse=True)
+        result = group_by_year_and_month(input_data, "date", reverse=True)
         expected = [
             {
                 "heading": "2022",
diff --git a/tna_utilities/datetime.py b/tna_utilities/datetime.py
index 6bbbcf8..8c0aa82 100644
--- a/tna_utilities/datetime.py
+++ b/tna_utilities/datetime.py
@@ -295,12 +295,24 @@ def pretty_datetime_range(  # noqa: C901
     return ""
 
 
-def pretty_age(date, just_now_seconds: int = 5, lowercase_first: bool = False) -> str:
+def pretty_age(
+    date: datetime.datetime, just_now_seconds: int = 5, lowercase_first: bool = False
+) -> str:
     if not date:
         raise ValueError("Date must be provided")
 
-    date = date.replace(microsecond=0)
-    now = datetime.datetime.now().replace(microsecond=0)
+    # Normalise input date to be timezone-aware in UTC for consistent comparison
+    if isinstance(date, datetime.datetime):
+        if date.tzinfo is None:
+            date = date.replace(tzinfo=datetime.timezone.utc)
+        date = date.replace(microsecond=0)
+    else:
+        # For date objects, convert to a UTC datetime at midnight
+        date = datetime.datetime.combine(
+            date, datetime.time.min, tzinfo=datetime.timezone.utc
+        )
+
+    now = datetime.datetime.now(datetime.timezone.utc).replace(microsecond=0)
 
     future = now < date
     delta = date - now if future else now - date
@@ -372,14 +384,14 @@ def is_today_in_date_range(
 
 def group_by_year_and_month(
     items: list[dict], date_key: str, reverse: bool = False
-) -> dict:  # noqa: C901
+) -> list[dict]:  # noqa: C901
     """
     Groups a list of items by year and month based on a date key in each item.
     """
 
     grouped = []
 
-    for item in items.get("items", []):
+    for item in items:
         if request_date := item.get(date_key):
             if isinstance(request_date, (datetime.datetime, datetime.date)):
                 request_datetime = request_date
@@ -438,9 +450,37 @@ def group_by_year_and_month(
         for month_group in year_group["items"]:
             month_group["items"].sort(
                 key=lambda x: (
-                    x.get(date_key)
+                    (
+                        x.get(date_key)
+                        if isinstance(
+                            x.get(date_key), (datetime.date, datetime.datetime)
+                        )
+                        else (
+                            get_date_from_string(x.get(date_key))
+                            if x.get(date_key) is not None
+                            else (
+                                datetime.datetime.max
+                                if reverse
+                                else datetime.datetime.min
+                            )
+                        )
+                    )
                     if isinstance(x.get(date_key), (datetime.date, datetime.datetime))
-                    else get_date_from_string(x.get(date_key))
+                    else (
+                        (
+                            get_date_from_string(x.get(date_key))
+                            if x.get(date_key) is not None
+                            else (
+                                datetime.datetime.max
+                                if reverse
+                                else datetime.datetime.min
+                            )
+                        )
+                        if isinstance(x.get(date_key), str)
+                        else (
+                            datetime.datetime.max if reverse else datetime.datetime.min
+                        )
+                    )
                 ),
                 reverse=reverse,
             )