diff --git a/lib/assert.js b/lib/assert.js
index 657ac6225d9833..e77ce6d66f2986 100644
--- a/lib/assert.js
+++ b/lib/assert.js
@@ -73,6 +73,22 @@ function lazyLoadComparison() {
   isPartialStrictEqual = comparison.isPartialStrictEqual;
 }
 
+function compareAsymetric(actual, expected) {
+  const isAsymetric = expected?.type === Symbol.for('blah');
+
+  if (!isAsymetric && typeof expected === 'object') {
+    for (const key of ObjectKeys(expected)) {
+      if (!compareAsymetric(actual[key], expected[key])) {
+        return false;
+      }
+    }
+
+    return true;
+  }
+
+  return (isAsymetric && expected.match(actual));
+}
+
 let warned = false;
 
 // The assert module provides functions that throw
@@ -171,7 +187,7 @@ assert.equal = function equal(actual, expected, message) {
     throw new ERR_MISSING_ARGS('actual', 'expected');
   }
   // eslint-disable-next-line eqeqeq
-  if (actual != expected && (!NumberIsNaN(actual) || !NumberIsNaN(expected))) {
+  if (!compareAsymetric(actual, expected) && (actual != expected && (!NumberIsNaN(actual) || !NumberIsNaN(expected)))) {
     innerFail({
       actual,
       expected,
@@ -313,7 +329,7 @@ assert.strictEqual = function strictEqual(actual, expected, message) {
   if (arguments.length < 2) {
     throw new ERR_MISSING_ARGS('actual', 'expected');
   }
-  if (!ObjectIs(actual, expected)) {
+  if (!ObjectIs(actual, expected) || !compareAsymetric(actual, expected)) {
     innerFail({
       actual,
       expected,
@@ -324,6 +340,39 @@ assert.strictEqual = function strictEqual(actual, expected, message) {
   }
 };
 
+assert.asymetric = {
+  any: function any(sample) {
+    return {
+      type: Symbol.for('blah'),
+      match: function match(other) {
+        if (sample === String) {
+          return typeof other === 'string' || other instanceof String;
+        }
+
+        if (sample === Number) {
+          return typeof other === 'number' || other instanceof Number;
+        }
+
+        if (sample === Object) {
+          return typeof other === 'number' || other instanceof Object;
+        }
+
+        return other instanceof sample;
+      },
+      getExpectedType() {
+        if (sample === String) return 'String';
+        if (sample === Number) return 'Number';
+        if (sample === Object) return 'Object';
+
+        https://github.com/jestjs/jest/blob/611d1a4ba0008d67b5dcda485177f0813b2b573e/packages/expect/src/asymmetricMatchers.ts#L27
+        return sample.toString();
+      },
+
+      toString() { return `Any<${this.getExpectedType()}>`; }
+    };
+  }
+};
+
 /**
  * The strict non-equivalence assertion tests for any strict inequality.
  * @param {any} actual
diff --git a/lib/internal/assert/assertion_error.js b/lib/internal/assert/assertion_error.js
index d654ca5038bbab..0a82c15f6ee04b 100644
--- a/lib/internal/assert/assertion_error.js
+++ b/lib/internal/assert/assertion_error.js
@@ -181,10 +181,20 @@ function isSimpleDiff(actual, inspectedActual, expected, inspectedExpected) {
 function createErrDiff(actual, expected, operator, customMessage) {
   operator = checkOperator(actual, expected, operator);
 
+  const newExpected = Object.keys(expected).reduce((acc, key) => {
+    const val = expected[key];
+    if (val?.type === Symbol.for('blah')) {
+      acc[key] = val.toString();
+      return acc;
+    }
+    acc[key] = expected[key];
+    return acc;
+  }, {});
+
   let skipped = false;
   let message = '';
   const inspectedActual = inspectValue(actual);
-  const inspectedExpected = inspectValue(expected);
+  const inspectedExpected = inspectValue(newExpected);
   const inspectedSplitActual = StringPrototypeSplit(inspectedActual, '\n');
   const inspectedSplitExpected = StringPrototypeSplit(inspectedExpected, '\n');
   const showSimpleDiff = isSimpleDiff(actual, inspectedSplitActual, expected, inspectedSplitExpected);
@@ -242,6 +252,19 @@ function addEllipsis(string) {
   return string;
 }
 
+function transformAsymetric(value) {
+  let newValue = value;
+  if (value?.type === Symbol.for('blah')) {
+    newValue = value.toString();
+  } else if (typeof value === 'object') {
+    for (const key in value) {
+      newValue[key] = transformAsymetric(value[key]);
+    }
+  }
+
+  return newValue;
+}
+
 class AssertionError extends Error {
   constructor(options) {
     validateObject(options, 'options');
@@ -258,6 +281,8 @@ class AssertionError extends Error {
       expected,
     } = options;
 
+    expected = transformAsymetric(expected);
+
     const limit = Error.stackTraceLimit;
     if (isErrorStackTraceLimitWritable()) Error.stackTraceLimit = 0;
 
diff --git a/lib/internal/util/comparisons.js b/lib/internal/util/comparisons.js
index 7eb9c72119eb92..8042c75cf808a5 100644
--- a/lib/internal/util/comparisons.js
+++ b/lib/internal/util/comparisons.js
@@ -182,6 +182,11 @@ function innerDeepEqual(val1, val2, mode, memos) {
     return val1 !== 0 || ObjectIs(val1, val2) || mode === kLoose;
   }
 
+  // TODO: prop "type" has to be a symbol itself
+  if (val2?.type === Symbol.for('blah')) {
+    return val2.match(val1);
+  }
+
   // Check more closely if val1 and val2 are equal.
   if (mode !== kLoose) {
     if (typeof val1 === 'number') {
diff --git a/test/parallel/test-assert-asymetric-matchers.mjs b/test/parallel/test-assert-asymetric-matchers.mjs
new file mode 100644
index 00000000000000..7d4618a6714101
--- /dev/null
+++ b/test/parallel/test-assert-asymetric-matchers.mjs
@@ -0,0 +1,44 @@
+import assert from 'node:assert';
+
+assert.equal('Node.js', assert.asymetric.any(String));
+assert.equal(new String('Node.js'), assert.asymetric.any(String));
+assert.equal(123, assert.asymetric.any(Number));
+assert.equal(4.56, assert.asymetric.any(Number));
+assert.equal(new Number(123), assert.asymetric.any(Number));
+assert.equal({name: 'foo'}, { name: assert.asymetric.any(Number) });
+assert.deepStrictEqual({
+  a: {
+    b: {
+      c: 42,
+      d: 'edy',
+      e: {
+        f: 'foo',
+        g: 'bar'
+      }
+    }
+  }
+}, {
+  a: {
+    b: {
+      c: assert.asymetric.any(Number),
+      d: assert.asymetric.any(String),
+      e: assert.asymetric.any(Object)
+    }
+  }
+});
+
+// assert.equal(123, assert.asymetric.any(String));
+// assert.equal('123', assert.asymetric.any(Number));
+// assert.strictEqual({name: 'foo'}, { name: assert.asymetric.any(String) });
+// assert.equal({name: 'bar'}, { name: assert.asymetric.any(Number) });
+// assert.throws(() => {
+//   assert.deepStrictEqual(
+//     {
+//       name: 'foo',
+//     },
+//     {
+//       name: assert.asymetric.any(Number),
+//     }
+//   );
+// });
+