diff --git a/src/parser/cxx/ast_interpreter.cc b/src/parser/cxx/ast_interpreter.cc
index 9f8e2be3..2f0bb3b3 100644
--- a/src/parser/cxx/ast_interpreter.cc
+++ b/src/parser/cxx/ast_interpreter.cc
@@ -122,6 +122,18 @@ struct ASTInterpreter::NewPlacementResult {};
 
 struct ASTInterpreter::NestedNamespaceSpecifierResult {};
 
+struct ASTInterpreter::ToBool {
+  ASTInterpreter& interp;
+
+  auto operator()(const StringLiteral*) const -> std::optional<bool> {
+    return true;
+  }
+
+  auto operator()(const auto& value) const -> std::optional<bool> {
+    return bool(value);
+  }
+};
+
 struct ASTInterpreter::UnitVisitor {
   ASTInterpreter& accept;
 
@@ -2193,10 +2205,17 @@ auto ASTInterpreter::ExpressionVisitor::operator()(BinaryExpressionAST* ast)
 auto ASTInterpreter::ExpressionVisitor::operator()(
     ConditionalExpressionAST* ast) -> ExpressionResult {
   auto conditionResult = accept(ast->condition);
-  auto iftrueExpressionResult = accept(ast->iftrueExpression);
-  auto iffalseExpressionResult = accept(ast->iffalseExpression);
 
-  return ExpressionResult{std::nullopt};
+  if (!conditionResult.has_value()) return std::nullopt;
+
+  if (accept.toBool(conditionResult.value())) {
+    auto result = accept(ast->iftrueExpression);
+    return result;
+  }
+
+  auto result = accept(ast->iffalseExpression);
+
+  return result;
 }
 
 auto ASTInterpreter::ExpressionVisitor::operator()(YieldExpressionAST* ast)
@@ -3176,4 +3195,8 @@ auto ASTInterpreter::evaluate(ExpressionAST* ast) -> std::optional<ConstValue> {
   return result;
 }
 
+auto ASTInterpreter::toBool(const ConstValue& value) -> std::optional<bool> {
+  return std::visit(ToBool{*this}, value);
+}
+
 }  // namespace cxx
diff --git a/src/parser/cxx/ast_interpreter.h b/src/parser/cxx/ast_interpreter.h
index a28a807f..73b83492 100644
--- a/src/parser/cxx/ast_interpreter.h
+++ b/src/parser/cxx/ast_interpreter.h
@@ -43,6 +43,8 @@ class ASTInterpreter {
 
   [[nodiscard]] auto evaluate(ExpressionAST* ast) -> std::optional<ConstValue>;
 
+  [[nodiscard]] auto toBool(const ConstValue& value) -> std::optional<bool>;
+
  private:
   using ExpressionResult = std::optional<ConstValue>;
 
@@ -116,6 +118,9 @@ class ASTInterpreter {
   struct AttributeSpecifierVisitor;
   struct AttributeTokenVisitor;
 
+  // ops
+  struct ToBool;
+
   // run on the base nodes
   [[nodiscard]] auto operator()(UnitAST* ast) -> UnitResult;
   [[nodiscard]] auto operator()(DeclarationAST* ast) -> DeclarationResult;
diff --git a/src/parser/cxx/type_checker.cc b/src/parser/cxx/type_checker.cc
index 152e53df..e78ccf0f 100644
--- a/src/parser/cxx/type_checker.cc
+++ b/src/parser/cxx/type_checker.cc
@@ -1624,8 +1624,6 @@ auto TypeChecker::Visitor::usual_arithmetic_conversion(ExpressionAST*& expr,
   (void)lvalue_to_rvalue_conversion(other);
   adjust_cv(other);
 
-  if (control()->is_same(expr->type, other->type)) return expr->type;
-
   ExpressionAST* savedExpr = expr;
   ExpressionAST* savedOther = other;
 
@@ -1991,8 +1989,15 @@ void TypeChecker::Visitor::check_subtraction(BinaryExpressionAST* ast) {
   }
 
   if (control()->is_pointer(ast->rightExpression->type)) {
-    if (control()->is_same(ast->leftExpression->type,
-                           ast->rightExpression->type)) {
+    auto leftElementType =
+        control()->get_element_type(ast->leftExpression->type);
+    (void)strip_cv(leftElementType);
+
+    auto rightElementType =
+        control()->get_element_type(ast->rightExpression->type);
+    (void)strip_cv(rightElementType);
+
+    if (control()->is_same(leftElementType, rightElementType)) {
       ast->type = control()->getLongIntType();  // TODO: ptrdiff_t
     } else {
       error(ast->opLoc,
diff --git a/tests/unit_tests/sema/subtraction_01.cc b/tests/unit_tests/sema/subtraction_01.cc
new file mode 100644
index 00000000..80706061
--- /dev/null
+++ b/tests/unit_tests/sema/subtraction_01.cc
@@ -0,0 +1,33 @@
+// RUN: %cxx -verify -fcheck %s
+
+auto main() -> int {
+  char* p;
+  const char* cp;
+  void* vp;
+  int i = 0;
+  short s = 0;
+
+  static_assert(__is_same(int, decltype('a' - '0')));
+  static_assert(__is_same(int, decltype('a' - 0)));
+  static_assert(__is_same(int, decltype('a' - s)));
+  static_assert(__is_same(long, decltype('a' - 1l)));
+  static_assert(__is_same(unsigned, decltype('a' - 1u)));
+
+  static_assert(__is_same(decltype(p), decltype(p - 0)));
+  static_assert(__is_same(decltype(p), decltype(p - i)));
+
+  static_assert(__is_same(long, decltype(p - p)));
+  static_assert(__is_same(long, decltype(p - cp)));
+
+  // clang-format off
+
+  // expected-error@1 {{'char*' and 'void*' are not pointers to compatible types}}
+  p - vp;
+
+  // expected-error@1 {{invalid operands to binary expression 'int' and 'char*'}}
+  0 - p;
+
+  // clang-format on
+
+  return 0;
+}
\ No newline at end of file