diff --git a/crates/nu-data/src/base.rs b/crates/nu-data/src/base.rs
index 0f6f5f2d1f..f0b76d7acb 100644
--- a/crates/nu-data/src/base.rs
+++ b/crates/nu-data/src/base.rs
@@ -164,8 +164,8 @@ pub fn coerce_compare_primitive(
         (Date(left), Date(right)) => CompareValues::Date(*left, *right),
         (Date(left), Duration(right)) => CompareValues::DateDuration(*left, right.clone()),
         (Boolean(left), Boolean(right)) => CompareValues::Booleans(*left, *right),
-        (Boolean(left), Nothing) => CompareValues::Booleans(*left, false),
-        (Nothing, Boolean(right)) => CompareValues::Booleans(false, *right),
+        (Boolean(left), Nothing) => CompareValues::Ints(if *left { 1 } else { 0 }, -1),
+        (Nothing, Boolean(right)) => CompareValues::Ints(-1, if *right { 1 } else { 0 }),
         (String(left), Nothing) => CompareValues::String(left.clone(), std::string::String::new()),
         (Nothing, String(right)) => {
             CompareValues::String(std::string::String::new(), right.clone())
diff --git a/crates/nu-engine/tests/evaluate/subexpression.rs b/crates/nu-engine/tests/evaluate/subexpression.rs
index 20aa7c3ab1..d1713568f0 100644
--- a/crates/nu-engine/tests/evaluate/subexpression.rs
+++ b/crates/nu-engine/tests/evaluate/subexpression.rs
@@ -34,3 +34,21 @@ fn compare_to_nothing() {
     );
     assert_eq!(actual.out, "true");
 }
+
+#[test]
+fn compare_nothing_and_boolean() {
+    let actual = nu!(
+        cwd: ".",
+        r#"
+        if $true == $nothing {echo $true} {echo $false}
+        "#
+    );
+    assert_eq!(actual.out, "false");
+    let actual = nu!(
+        cwd: ".",
+        r#"
+        if $false == $nothing {echo $true} {echo $false}
+        "#
+    );
+    assert_eq!(actual.out, "false");
+}