diff --git a/src/daft-core/src/array/ops/cast.rs b/src/daft-core/src/array/ops/cast.rs
index a9b9b8c552..482f2ab168 100644
--- a/src/daft-core/src/array/ops/cast.rs
+++ b/src/daft-core/src/array/ops/cast.rs
@@ -14,8 +14,8 @@ use crate::{
             FixedShapeTensorArray, ImageArray, LogicalArray, LogicalArrayImpl, TensorArray,
             TimestampArray,
         },
-        DaftArrowBackedType, DaftLogicalType, DataType, Field, ImageMode, TimeUnit, UInt64Array,
-        Utf8Array,
+        DaftArrowBackedType, DaftLogicalType, DataType, Field, ImageMode, Int64Array, TimeUnit,
+        UInt64Array, Utf8Array,
     },
     series::{IntoSeries, Series},
     with_match_daft_logical_primitive_types,
@@ -255,14 +255,12 @@ where
 
 impl DateArray {
     pub fn cast(&self, dtype: &DataType) -> DaftResult<Series> {
-        // We need to handle casts that Arrow doesn't allow, but our type-system does
-
         let date_array = self
             .as_arrow()
             .clone()
             .to(arrow2::datatypes::DataType::Date32);
-
         match dtype {
+            DataType::Date => Ok(self.clone().into_series()),
             DataType::Utf8 => {
                 // TODO: we should move this into our own strftime kernel
                 let year_array = compute::temporal::year(&date_array)?;
@@ -279,11 +277,27 @@ impl DateArray {
                     .collect();
                 Ok(Utf8Array::from((self.name(), Box::new(date_str))).into_series())
             }
+            DataType::Int32 => Ok(self.physical.clone().into_series()),
             DataType::Float32 => self.cast(&DataType::Int32)?.cast(&DataType::Float32),
             DataType::Float64 => self.cast(&DataType::Int32)?.cast(&DataType::Float64),
+            DataType::Timestamp(tu, _) => {
+                let days_to_unit: i64 = match tu {
+                    TimeUnit::Nanoseconds => 24 * 3_600_000_000_000,
+                    TimeUnit::Microseconds => 24 * 3_600_000_000,
+                    TimeUnit::Milliseconds => 24 * 3_600_000,
+                    TimeUnit::Seconds => 24 * 3_600,
+                };
+
+                let units_per_day = Int64Array::from(("units", vec![days_to_unit])).into_series();
+                let unit_since_epoch = ((&self.physical.clone().into_series()) * &units_per_day)?;
+                unit_since_epoch.cast(dtype)
+            }
             #[cfg(feature = "python")]
             DataType::Python => cast_logical_to_python_array(self, dtype),
-            _ => arrow_cast(&self.physical, dtype),
+            _ => Err(DaftError::TypeError(format!(
+                "Cannot cast Date to {}",
+                dtype
+            ))),
         }
     }
 }
@@ -348,9 +362,7 @@ impl TimestampArray {
     pub fn cast(&self, dtype: &DataType) -> DaftResult<Series> {
         match dtype {
             DataType::Timestamp(..) => arrow_logical_cast(self, dtype),
-            DataType::Date => Err(DaftError::TypeError(
-                "Cannot cast Timestamp to Date, use .date() instead.".to_string(),
-            )),
+            DataType::Date => Ok(self.date()?.into_series()),
             DataType::Utf8 => {
                 let DataType::Timestamp(unit, timezone) = self.data_type() else {
                     panic!("Wrong dtype for TimestampArray: {}", self.data_type())
diff --git a/src/daft-core/src/datatypes/binary_ops.rs b/src/daft-core/src/datatypes/binary_ops.rs
index 3353bde863..7ef1818c30 100644
--- a/src/daft-core/src/datatypes/binary_ops.rs
+++ b/src/daft-core/src/datatypes/binary_ops.rs
@@ -40,11 +40,16 @@ impl DataType {
                 (s, o) if s.is_physical() && o.is_physical() => {
                     Ok((Boolean, None, try_physical_supertype(s, o)?))
                 }
-                (Timestamp(..) | Date, Timestamp(..) | Date) => {
+                (Timestamp(..), Timestamp(..)) => {
                     let intermediate_type = try_get_supertype(self, other)?;
                     let pt = intermediate_type.to_physical();
                     Ok((Boolean, Some(intermediate_type), pt))
                 }
+                (Timestamp(..), Date) | (Date, Timestamp(..)) => {
+                    let intermediate_type = Date;
+                    let pt = intermediate_type.to_physical();
+                    Ok((Boolean, Some(intermediate_type), pt))
+                }
                 _ => Err(DaftError::TypeError(format!(
                     "Cannot perform comparison on types: {}, {}",
                     self, other
diff --git a/tests/series/test_cast.py b/tests/series/test_cast.py
index 62b4e6ebad..e07769d4ce 100644
--- a/tests/series/test_cast.py
+++ b/tests/series/test_cast.py
@@ -760,3 +760,13 @@ def test_series_cast_struct_add_col() -> None:
     casted = series.cast(cast_to)
     assert casted.datatype() == cast_to
     assert casted.to_pylist() == [{**x, "baz": None} for x in data.to_pylist()]
+
+
+def test_cast_date_to_timestamp():
+    from datetime import date
+
+    input = Series.from_pylist([date(2022, 1, 6)])
+    casted = input.cast(DataType.timestamp("us", "UTC"))
+    # DO ASSERT AS TIMESTAMP
+    back = casted.dt.date()
+    assert (input == back).to_pylist() == [True]
diff --git a/tests/series/test_comparisons.py b/tests/series/test_comparisons.py
index eca23a53cd..811670de40 100644
--- a/tests/series/test_comparisons.py
+++ b/tests/series/test_comparisons.py
@@ -714,8 +714,14 @@ def test_compare_timestamps_and_int():
 
 def test_compare_timestamps_tz_date():
     tz1 = Series.from_pylist([datetime(2022, 1, 1, tzinfo=pytz.utc)])
-    Series.from_pylist([date(2022, 1, 1)])
-    assert (tz1 == tz1).to_pylist() == [True]
+    tz2 = Series.from_pylist([date(2022, 1, 1)])
+    assert (tz1 == tz2).to_pylist() == [True]
+
+
+def test_compare_lt_timestamps_tz_date():
+    tz1 = Series.from_pylist([datetime(2022, 1, 1, tzinfo=pytz.utc)])
+    tz2 = Series.from_pylist([date(2022, 1, 6)])
+    assert (tz1 < tz2).to_pylist() == [True]
 
 
 @pytest.mark.parametrize("tu1, tu2", itertools.product(["ns", "us", "ms"], repeat=2))