diff --git a/packages/babel-plugin-transform-optional-chaining/src/index.js b/packages/babel-plugin-transform-optional-chaining/src/index.js
index 49ff4c81e7..9c4b7805a5 100644
--- a/packages/babel-plugin-transform-optional-chaining/src/index.js
+++ b/packages/babel-plugin-transform-optional-chaining/src/index.js
@@ -1,6 +1,78 @@
 import syntaxOptionalChaining from "babel-plugin-syntax-optional-chaining";
 
 export default function ({ types: t }) {
+  function optional(path, key, replacementPath, needsContext = false, loose = false) {
+    const { scope } = path;
+    const optionals = [path.node];
+
+    let objectPath = path.get(key);
+    while (objectPath.isMemberExpression()) {
+      const { node } = objectPath;
+      if (node.optional) {
+        optionals.push(node);
+      }
+
+      objectPath = objectPath.get("object");
+    }
+
+    for (let i = optionals.length - 1; i >= 0; i--) {
+      const node = optionals[i];
+      node.optional = false;
+
+      const replaceKey = i == 0 ? key : "object";
+      const atCall = needsContext && i == 0;
+
+      const chain = node[replaceKey];
+
+      let ref;
+      let check;
+      if (loose && atCall) {
+        // If we are using a loose transform (avoiding a Function#call) and we are at the call,
+        // we can avoid a needless memoize.
+        ref = chain;
+        check = ref;
+      } else {
+        ref = scope.maybeGenerateMemoised(chain);
+        if (ref) {
+          check = t.assignmentExpression("=", ref, chain);
+          node[replaceKey] = ref;
+        } else {
+          ref = chain;
+          check = chain;
+        }
+      }
+
+      // Ensure call expressions have the proper `this`
+      // `foo.bar()` has context `foo`.
+      if (atCall && t.isMemberExpression(chain)) {
+        if (loose) {
+          // To avoid a Function#call, we can instead re-grab the property from the context object.
+          // `a.?b.?()` translates roughly to `_a.b != null && _a.b()`
+          node.callee = chain
+        } else {
+          // Otherwise, we need to memoize the context object, and change the call into a Function#call.
+          // `a.?b.?()` translates roughly to `(_b = _a.b) != null && _b.call(_a)`
+          const { object } = chain;
+          const context = scope.generateUidIdentifierBasedOnNode(object);
+
+          scope.push({ id: context });
+          chain.object = t.assignmentExpression("=", context, object);
+
+          node.arguments.unshift(context);
+          node.callee = t.memberExpression(node.callee, t.identifier("call"));
+        }
+      }
+
+      replacementPath.replaceWith(t.conditionalExpression(
+        t.binaryExpression("==", check, t.nullLiteral()),
+        scope.buildUndefinedNode(),
+        replacementPath.node
+      ));
+
+      replacementPath = replacementPath.get("alternate");
+    }
+  }
+
   return {
     inherits: syntaxOptionalChaining,
 
@@ -10,28 +82,25 @@ export default function ({ types: t }) {
           return;
         }
 
-        const { scope, node } = path;
-        const { object } = node;
+        const replace = path.find(path => {
+          const { parentPath } = path;
+          if (parentPath.isStatement()) {
+            return true;
+          }
 
-        node.optional = false;
+          if (path.key == "left" && parentPath.isAssignmentExpression()) {
+            return false;
+          }
+          if (path.key == "object" && parentPath.isMemberExpression()) {
+            return false;
+          }
+          if (path.key == "callee" && (parentPath.isCallExpression() || parentPath.isNewExpression())) {
+            return false;
+          }
+          return true;
+        });
 
-        const ref = scope.generateUidIdentifierBasedOnNode(object);
-        scope.push({ id: ref });
-        node.object = ref;
-
-        let parent = path;
-        let expression = path;
-        while (parent.listKey === undefined) {
-          expression = parent;
-          parent = parent.parentPath;
-        }
-
-        const replace = parent.isExpression() ? parent : expression;
-        replace.replaceWith(t.conditionalExpression(
-          t.binaryExpression("==", t.assignmentExpression("=", ref, object), t.nullLiteral()),
-          scope.buildUndefinedNode(),
-          replace.node
-        ));
+        optional(path, "object", replace);
       },
 
       "NewExpression|CallExpression"(path) {
@@ -39,29 +108,7 @@ export default function ({ types: t }) {
           return;
         }
 
-        const { scope, node } = path;
-        const { callee } = node;
-
-        node.optional = false;
-
-        const ref = scope.generateUidIdentifierBasedOnNode(callee);
-        scope.push({ id: ref });
-        node.callee = ref;
-
-        if (t.isMemberExpression(callee) && !t.isNewExpression(node)) {
-          const context = scope.generateUidIdentifierBasedOnNode(callee.object);
-          scope.push({ id: context });
-          callee.object = t.assignmentExpression("=", context, callee.object);
-
-          node.arguments.unshift(context);
-          node.callee = t.memberExpression(node.callee, t.identifier("call"));
-        }
-
-        path.replaceWith(t.conditionalExpression(
-          t.binaryExpression("==", t.assignmentExpression("=", ref, callee), t.nullLiteral()),
-          scope.buildUndefinedNode(),
-          node
-        ));
+        optional(path, "callee", path, path.isCallExpression(), this.opts.loose);
       },
     },
   };
diff --git a/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/assignement/actual.js b/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/assignement/actual.js
index b9405035c9..b7d9cee953 100644
--- a/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/assignement/actual.js
+++ b/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/assignement/actual.js
@@ -1,3 +1,7 @@
 a?.b = 42
 
 a?.b?.c?.d = 42
+
+a?.b?.c?.d++
+
+a?.b?.c?.d += 1
diff --git a/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/assignement/expected.js b/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/assignement/expected.js
index 86ba0f57ef..5670c0f0e1 100644
--- a/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/assignement/expected.js
+++ b/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/assignement/expected.js
@@ -1,5 +1,9 @@
-var _a, _a$b$c, _a$b, _a2;
+var _a, _a2, _a2$b, _a2$b$c, _a3, _a3$b, _a3$b$c, _a4, _a4$b, _a4$b$c;
 
 (_a = a) == null ? void 0 : _a.b = 42;
 
-(_a2 = a) == null ? void 0 : (_a$b = _a2.b) == null ? void 0 : (_a$b$c = _a$b.c) == null ? void 0 : _a$b$c.d = 42;
\ No newline at end of file
+(_a2 = a) == null ? void 0 : (_a2$b = _a2.b) == null ? void 0 : (_a2$b$c = _a2$b.c) == null ? void 0 : _a2$b$c.d = 42;
+
+(_a3 = a) == null ? void 0 : (_a3$b = _a3.b) == null ? void 0 : (_a3$b$c = _a3$b.c) == null ? void 0 : _a3$b$c.d++;
+
+(_a4 = a) == null ? void 0 : (_a4$b = _a4.b) == null ? void 0 : (_a4$b$c = _a4$b.c) == null ? void 0 : _a4$b$c.d += 1;
\ No newline at end of file
diff --git a/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/containers/expected.js b/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/containers/expected.js
index 811e1603a0..b0dc489b21 100644
--- a/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/containers/expected.js
+++ b/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/containers/expected.js
@@ -1,8 +1,8 @@
 var _user$address, _user$address2, _a, _a2;
 
 var street = (_user$address = user.address) == null ? void 0 : _user$address.street;
-(_user$address2 = user.address) == null ? void 0 : street = _user$address2.street;
+street = (_user$address2 = user.address) == null ? void 0 : _user$address2.street;
 
 test((_a = a) == null ? void 0 : _a.b, 1);
 
-1, (_a2 = a) == null ? void 0 : _a2.b, 2;
+1, (_a2 = a) == null ? void 0 : _a2.b, 2;
\ No newline at end of file
diff --git a/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/delete/expected.js b/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/delete/expected.js
index 49afe9cd6e..d1c9cb8617 100644
--- a/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/delete/expected.js
+++ b/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/delete/expected.js
@@ -1,5 +1,5 @@
-var _a, _a$b$c, _a$b, _a2;
+var _a, _a2, _a2$b, _a2$b$c;
 
-(_a = a) == null ? void 0 : delete _a.b;
+delete ((_a = a) == null ? void 0 : _a.b);
 
-(_a2 = a) == null ? void 0 : (_a$b = _a2.b) == null ? void 0 : (_a$b$c = _a$b.c) == null ? void 0 : delete _a$b$c.d;
\ No newline at end of file
+delete ((_a2 = a) == null ? void 0 : (_a2$b = _a2.b) == null ? void 0 : (_a2$b$c = _a2$b.c) == null ? void 0 : _a2$b$c.d);
\ No newline at end of file
diff --git a/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/function-call-loose/actual.js b/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/function-call-loose/actual.js
new file mode 100644
index 0000000000..9499c5f20e
--- /dev/null
+++ b/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/function-call-loose/actual.js
@@ -0,0 +1,7 @@
+foo?.(foo);
+
+foo?.bar()
+
+foo.bar?.(foo.bar, false)
+
+foo?.bar?.(foo.bar, true)
diff --git a/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/function-call-loose/expected.js b/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/function-call-loose/expected.js
new file mode 100644
index 0000000000..7c40785d92
--- /dev/null
+++ b/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/function-call-loose/expected.js
@@ -0,0 +1,9 @@
+var _foo, _foo2;
+
+foo == null ? void 0 : foo(foo);
+
+(_foo = foo) == null ? void 0 : _foo.bar();
+
+foo.bar == null ? void 0 : foo.bar(foo.bar, false);
+
+(_foo2 = foo) == null ? void 0 : _foo2.bar == null ? void 0 : _foo2.bar(foo.bar, true);
diff --git a/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/function-call-loose/options.json b/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/function-call-loose/options.json
new file mode 100644
index 0000000000..acc83616f9
--- /dev/null
+++ b/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/function-call-loose/options.json
@@ -0,0 +1,3 @@
+{
+  "plugins": [["transform-optional-chaining", {"loose": true}]]
+}
diff --git a/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/function-call/expected.js b/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/function-call/expected.js
index 0b6f985356..1df03edc8c 100644
--- a/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/function-call/expected.js
+++ b/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/function-call/expected.js
@@ -1,4 +1,4 @@
-var _foo, _foo2, _foo$bar, _foo3, _foo$bar2, _foo4, _foo5;
+var _foo, _foo2, _foo$bar, _foo3, _foo4, _foo4$bar, _foo5;
 
 (_foo = foo) == null ? void 0 : _foo(foo);
 
@@ -6,4 +6,4 @@ var _foo, _foo2, _foo$bar, _foo3, _foo$bar2, _foo4, _foo5;
 
 (_foo$bar = (_foo3 = foo).bar) == null ? void 0 : _foo$bar.call(_foo3, foo.bar, false);
 
-(_foo5 = _foo4 = foo) == null ? void 0 : (_foo$bar2 = _foo5.bar) == null ? void 0 : _foo$bar2.call(_foo4, foo.bar, true);
\ No newline at end of file
+(_foo4 = foo) == null ? void 0 : (_foo4$bar = (_foo5 = _foo4).bar) == null ? void 0 : _foo4$bar.call(_foo5, foo.bar, true);
\ No newline at end of file
diff --git a/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/member-access/actual.js b/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/member-access/actual.js
index 83447e76d5..d6a9752544 100644
--- a/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/member-access/actual.js
+++ b/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/member-access/actual.js
@@ -1,3 +1,11 @@
 foo?.bar
 
 a?.b.c?.d.e
+
+orders?.[0].price
+
+orders?.[0]?.price
+
+orders[client?.key].price
+
+orders[client.key]?.price
diff --git a/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/member-access/expected.js b/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/member-access/expected.js
index a8a381af7a..ffc9f8bc4e 100644
--- a/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/member-access/expected.js
+++ b/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/member-access/expected.js
@@ -1,5 +1,13 @@
-var _foo, _a$b$c, _a;
+var _foo, _a, _a$b$c, _orders, _orders2, _orders2$, _client, _orders$client$key;
 
 (_foo = foo) == null ? void 0 : _foo.bar;
 
-(_a = a) == null ? void 0 : (_a$b$c = _a.b.c) == null ? void 0 : _a$b$c.d.e;
\ No newline at end of file
+(_a = a) == null ? void 0 : (_a$b$c = _a.b.c) == null ? void 0 : _a$b$c.d.e;
+
+(_orders = orders) == null ? void 0 : _orders[0].price;
+
+(_orders2 = orders) == null ? void 0 : (_orders2$ = _orders2[0]) == null ? void 0 : _orders2$.price;
+
+orders[(_client = client) == null ? void 0 : _client.key].price;
+
+(_orders$client$key = orders[client.key]) == null ? void 0 : _orders$client$key.price;
\ No newline at end of file
diff --git a/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/memoize-loose/actual.js b/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/memoize-loose/actual.js
new file mode 100644
index 0000000000..ffe543adde
--- /dev/null
+++ b/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/memoize-loose/actual.js
@@ -0,0 +1,21 @@
+function test(foo) {
+  foo?.bar;
+
+  foo?.bar?.baz;
+
+  foo?.(foo);
+
+  foo?.bar()
+
+  foo.bar?.(foo.bar, false)
+
+  foo?.bar?.(foo.bar, true)
+
+  foo.bar?.baz(foo.bar, false)
+
+  foo?.bar?.baz(foo.bar, true)
+
+  foo.bar?.baz?.(foo.bar, false)
+
+  foo?.bar?.baz?.(foo.bar, true)
+}
diff --git a/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/memoize-loose/expected.js b/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/memoize-loose/expected.js
new file mode 100644
index 0000000000..66f4809d09
--- /dev/null
+++ b/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/memoize-loose/expected.js
@@ -0,0 +1,23 @@
+function test(foo) {
+  var _foo$bar, _foo$bar2, _foo$bar3, _foo$bar4, _foo$bar5;
+
+  foo == null ? void 0 : foo.bar;
+
+  foo == null ? void 0 : (_foo$bar = foo.bar) == null ? void 0 : _foo$bar.baz;
+
+  foo == null ? void 0 : foo(foo);
+
+  foo == null ? void 0 : foo.bar();
+
+  foo.bar == null ? void 0 : foo.bar(foo.bar, false);
+
+  foo == null ? void 0 : foo.bar == null ? void 0 : foo.bar(foo.bar, true);
+
+  (_foo$bar2 = foo.bar) == null ? void 0 : _foo$bar2.baz(foo.bar, false);
+
+  foo == null ? void 0 : (_foo$bar3 = foo.bar) == null ? void 0 : _foo$bar3.baz(foo.bar, true);
+
+  (_foo$bar4 = foo.bar) == null ? void 0 : _foo$bar4.baz == null ? void 0 : _foo$bar4.baz(foo.bar, false);
+
+  foo == null ? void 0 : (_foo$bar5 = foo.bar) == null ? void 0 : _foo$bar5.baz == null ? void 0 : _foo$bar5.baz(foo.bar, true);
+}
\ No newline at end of file
diff --git a/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/memoize-loose/options.json b/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/memoize-loose/options.json
new file mode 100644
index 0000000000..acc83616f9
--- /dev/null
+++ b/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/memoize-loose/options.json
@@ -0,0 +1,3 @@
+{
+  "plugins": [["transform-optional-chaining", {"loose": true}]]
+}
diff --git a/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/memoize/actual.js b/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/memoize/actual.js
new file mode 100644
index 0000000000..ffe543adde
--- /dev/null
+++ b/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/memoize/actual.js
@@ -0,0 +1,21 @@
+function test(foo) {
+  foo?.bar;
+
+  foo?.bar?.baz;
+
+  foo?.(foo);
+
+  foo?.bar()
+
+  foo.bar?.(foo.bar, false)
+
+  foo?.bar?.(foo.bar, true)
+
+  foo.bar?.baz(foo.bar, false)
+
+  foo?.bar?.baz(foo.bar, true)
+
+  foo.bar?.baz?.(foo.bar, false)
+
+  foo?.bar?.baz?.(foo.bar, true)
+}
diff --git a/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/memoize/expected.js b/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/memoize/expected.js
new file mode 100644
index 0000000000..d02f52f934
--- /dev/null
+++ b/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/memoize/expected.js
@@ -0,0 +1,23 @@
+function test(foo) {
+  var _foo$bar, _foo$bar2, _foo, _foo$bar3, _foo2, _foo$bar4, _foo$bar5, _foo$bar6, _foo$bar6$baz, _foo$bar7, _foo$bar8, _foo$bar8$baz, _foo$bar9;
+
+  foo == null ? void 0 : foo.bar;
+
+  foo == null ? void 0 : (_foo$bar = foo.bar) == null ? void 0 : _foo$bar.baz;
+
+  foo == null ? void 0 : foo(foo);
+
+  foo == null ? void 0 : foo.bar();
+
+  (_foo$bar2 = (_foo = foo).bar) == null ? void 0 : _foo$bar2.call(_foo, foo.bar, false);
+
+  foo == null ? void 0 : (_foo$bar3 = (_foo2 = foo).bar) == null ? void 0 : _foo$bar3.call(_foo2, foo.bar, true);
+
+  (_foo$bar4 = foo.bar) == null ? void 0 : _foo$bar4.baz(foo.bar, false);
+
+  foo == null ? void 0 : (_foo$bar5 = foo.bar) == null ? void 0 : _foo$bar5.baz(foo.bar, true);
+
+  (_foo$bar6 = foo.bar) == null ? void 0 : (_foo$bar6$baz = (_foo$bar7 = _foo$bar6).baz) == null ? void 0 : _foo$bar6$baz.call(_foo$bar7, foo.bar, false);
+
+  foo == null ? void 0 : (_foo$bar8 = foo.bar) == null ? void 0 : (_foo$bar8$baz = (_foo$bar9 = _foo$bar8).baz) == null ? void 0 : _foo$bar8$baz.call(_foo$bar9, foo.bar, true);
+}
\ No newline at end of file
diff --git a/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/new/expected.js b/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/new/expected.js
index cf631ecfd0..241badcfdd 100644
--- a/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/new/expected.js
+++ b/packages/babel-plugin-transform-optional-chaining/test/fixtures/general/new/expected.js
@@ -1,10 +1,10 @@
-var _a, _a$b$c, _a$b, _a2, _a3, _a$b$c2, _a$b2, _a4, _b, _a$b3, _a5;
+var _a, _a2, _a2$b, _a2$b$c, _a3, _a4, _a4$b, _a4$b$c, _b, _a5, _a5$b;
 
 (_a = a) == null ? void 0 : new _a.b();
-(_a2 = a) == null ? void 0 : (_a$b = _a2.b) == null ? void 0 : (_a$b$c = _a$b.c) == null ? void 0 : new _a$b$c.d();
+(_a2 = a) == null ? void 0 : (_a2$b = _a2.b) == null ? void 0 : (_a2$b$c = _a2$b.c) == null ? void 0 : new _a2$b$c.d();
 
 (_a3 = a) == null ? void 0 : new _a3.b();
-(_a4 = a) == null ? void 0 : (_a$b2 = _a4.b) == null ? void 0 : (_a$b$c2 = _a$b2.c) == null ? void 0 : new _a$b$c2.d();
+(_a4 = a) == null ? void 0 : (_a4$b = _a4.b) == null ? void 0 : (_a4$b$c = _a4$b.c) == null ? void 0 : new _a4$b$c.d();
 
 (_b = b) == null ? void 0 : new _b(b);
-(_a5 = a) == null ? void 0 : (_a$b3 = _a5.b) == null ? void 0 : new _a$b3(a.b, true);
\ No newline at end of file
+(_a5 = a) == null ? void 0 : (_a5$b = _a5.b) == null ? void 0 : new _a5$b(a.b, true);
\ No newline at end of file