diff --git a/chat/global.d.ts b/chat/global.d.ts
index f943af7a5..34ba5119f 100644
--- a/chat/global.d.ts
+++ b/chat/global.d.ts
@@ -5,6 +5,7 @@ declare var process: {
 declare interface IChatMessage {
   id: string;
   username: string;
+  user_id?: string;
   avatar: string;
   hat: string;
   namecolor: string;
@@ -14,6 +15,7 @@ declare interface IChatMessage {
   text_html: string;
   time: number;
   quotes: null | string;
+  dm: boolean;
 }
 
 declare interface EmojiModSelection {
diff --git a/chat/package.json b/chat/package.json
index 8b91ac345..609fd31a2 100644
--- a/chat/package.json
+++ b/chat/package.json
@@ -1,6 +1,6 @@
 {
   "name": "chat",
-  "version": "0.1.18",
+  "version": "0.1.19",
   "main": "./src/index.tsx",
   "license": "MIT",
   "dependencies": {
diff --git a/chat/src/App.tsx b/chat/src/App.tsx
index 4e682770a..784a7ad40 100644
--- a/chat/src/App.tsx
+++ b/chat/src/App.tsx
@@ -36,7 +36,7 @@ function AppInner() {
   const { open, config } = useDrawer();
   const contentWrapper = useRef<HTMLDivElement>(null);
   const initiallyScrolledDown = useRef(false);
-  const { messages, quote } = useChat();
+  const { messages, quote, userToDm, updateUserToDm } = useChat();
 
   // See: https://css-tricks.com/the-trick-to-viewport-units-on-mobile/
   useEffect(() => {
@@ -120,6 +120,25 @@ function AppInner() {
                 <QuotedMessage />
               </div>
             )}
+            {userToDm && (
+              <div
+                className="App-bottom-extra text-primary"
+                style={{
+                  display: "flex",
+                  alignItems: "center",
+                  justifyContent: "space-between",
+                }}
+              >
+                <em>Directly messaging @{userToDm.username}</em>
+                <button
+                  type="button"
+                  className="btn btn-secondary"
+                  onClick={() => updateUserToDm(null)}
+                >
+                  Cancel
+                </button>
+              </div>
+            )}
             <UserInput />
             <UsersTyping />
           </div>
diff --git a/chat/src/features/chat/ChatMessage.css b/chat/src/features/chat/ChatMessage.css
index 45018a700..db9b6b751 100644
--- a/chat/src/features/chat/ChatMessage.css
+++ b/chat/src/features/chat/ChatMessage.css
@@ -1,7 +1,12 @@
 .ChatMessage {
   position: relative;
   padding-right: 1.5rem;
-  min-height: 28px;
+}
+
+.ChatMessage__isDm {
+  background: var(--gray-800);
+  border-top: 1px dashed var(--primary);
+  border-bottom: 1px dashed var(--primary);
 }
 
 .ChatMessage p {
diff --git a/chat/src/features/chat/ChatMessage.tsx b/chat/src/features/chat/ChatMessage.tsx
index dff4ac236..b74d0808e 100644
--- a/chat/src/features/chat/ChatMessage.tsx
+++ b/chat/src/features/chat/ChatMessage.tsx
@@ -43,6 +43,7 @@ export function ChatMessage({
     text_censored,
     time,
     quotes,
+    dm,
   } = message;
   const {
     id: userId,
@@ -51,7 +52,14 @@ export function ChatMessage({
     censored,
     themeColor,
   } = useRootContext();
-  const { messageLookup, deleteMessage, quoteMessage } = useChat();
+  const {
+    messageLookup,
+    userToDm,
+    quote,
+    deleteMessage,
+    quoteMessage,
+    updateUserToDm,
+  } = useChat();
   const [confirmedDelete, setConfirmedDelete] = useState(false);
   const quotedMessage = messageLookup[quotes];
   const content = censored ? text_censored : text_html;
@@ -72,9 +80,31 @@ export function ChatMessage({
     }
   }, [text, confirmedDelete]);
   const handleQuoteMessageAction = useCallback(() => {
+    updateUserToDm(null);
     quoteMessage(message);
     onToggleActions(message.id);
   }, [message, onToggleActions]);
+  const handleDirectMessage = useCallback(
+    (toggle?: boolean) => {
+      const userId = message.user_id ?? "";
+
+      if (userToDm && userToDm.id === userId) {
+        updateUserToDm(null);
+      } else {
+        updateUserToDm({
+          id: userId,
+          username: message.username,
+        });
+
+        quoteMessage(null);
+
+        if (toggle) {
+          onToggleActions(message.id);
+        }
+      }
+    },
+    [userToDm, message.id, message.user_id, message.username]
+  );
 
   useEffect(() => {
     if (!actionsOpen) {
@@ -85,12 +115,11 @@ export function ChatMessage({
   return (
     <div
       className={cx("ChatMessage", {
-        ChatMessage__showingUser: showUser,
-        ChatMessage__isMention: isMention,
+        ChatMessage__isDm: dm,
       })}
       id={id}
       style={
-        isMention
+        isMention && !dm
           ? {
               background: `#${themeColor}25`,
               borderLeft: `1px solid #${themeColor}`,
@@ -102,7 +131,21 @@ export function ChatMessage({
         <div className="ChatMessage-actions-button">
           <button
             className="btn btn-secondary"
-            onClick={() => quoteMessage(message)}
+            style={{
+              position: "relative",
+              top: 2,
+              left: -12
+            }}
+            onClick={() => handleDirectMessage()}
+          >
+            📨
+          </button>
+          <button
+            className="btn btn-secondary"
+            onClick={() => {
+              updateUserToDm(null);
+              quoteMessage(quote ? null : message);
+            }}
           >
             <i className="fas fa-reply" />
           </button>
@@ -116,6 +159,12 @@ export function ChatMessage({
       )}
       {actionsOpen && (
         <div className="ChatMessage-actions">
+          <button
+            className="btn btn-secondary ChatMessage-button"
+            onClick={() => handleDirectMessage(true)}
+          >
+            📨 DM @{message.username}
+          </button>
           <button
             className="btn btn-secondary ChatMessage-button"
             onClick={handleQuoteMessageAction}
@@ -157,6 +206,11 @@ export function ChatMessage({
           <QuotedMessageLink message={quotedMessage} />
         </div>
       )}
+      {dm && (
+        <small className="ChatMessage-quoted-link text-primary">
+          <em>(Sent only to you)</em>
+        </small>
+      )}
       <div className="ChatMessage-bottom">
         <div>
           <span
diff --git a/chat/src/features/chat/UserInput.tsx b/chat/src/features/chat/UserInput.tsx
index 2a516e7f7..511fc591e 100644
--- a/chat/src/features/chat/UserInput.tsx
+++ b/chat/src/features/chat/UserInput.tsx
@@ -13,7 +13,7 @@ import { EmojiDrawer, QuickEmojis } from "../emoji";
 import "./UserInput.css";
 
 export function UserInput() {
-  const { draft, sendMessage, updateDraft } = useChat();
+  const { draft, userToDm, sendMessage, updateDraft } = useChat();
   const builtChatInput = useRef<HTMLTextAreaElement>(null);
   const { visible, addQuery } = useEmojis();
   const form = useRef<HTMLFormElement>(null);
@@ -81,6 +81,12 @@ export function UserInput() {
     }
   }, []);
 
+  useEffect(() => {
+    if (userToDm) {
+      builtChatInput.current?.focus();
+    }
+  }, [userToDm])
+
   return (
     <form ref={form} className="UserInput" onSubmit={handleSendMessage}>
       {quickEmojis.length > 0 && (
diff --git a/chat/src/hooks/useChat.tsx b/chat/src/hooks/useChat.tsx
index 34d31275b..0c21ae4e4 100644
--- a/chat/src/hooks/useChat.tsx
+++ b/chat/src/hooks/useChat.tsx
@@ -22,6 +22,11 @@ enum ChatHandlers {
   SPEAK = "speak",
 }
 
+interface UserToDM {
+  id: string;
+  username: string;
+}
+
 interface ChatProviderContext {
   online: string[];
   typing: string[];
@@ -29,10 +34,12 @@ interface ChatProviderContext {
   draft: string;
   quote: null | IChatMessage;
   messageLookup: Record<string, IChatMessage>;
+  userToDm: null | UserToDM;
   updateDraft: React.Dispatch<React.SetStateAction<string>>;
   sendMessage(): void;
   quoteMessage(message: null | IChatMessage): void;
   deleteMessage(withText: string): void;
+  updateUserToDm(userToDm: UserToDM): void;
 }
 
 const ChatContext = createContext<ChatProviderContext>({
@@ -42,10 +49,12 @@ const ChatContext = createContext<ChatProviderContext>({
   draft: "",
   quote: null,
   messageLookup: {},
+  userToDm: null,
   updateDraft() {},
   sendMessage() {},
   quoteMessage() {},
   deleteMessage() {},
+  updateUserToDm() {},
 });
 
 const MINIMUM_TYPING_UPDATE_INTERVAL = 250;
@@ -60,6 +69,7 @@ export function ChatProvider({ children }: PropsWithChildren) {
   const lastDraft = useRef("");
   const [quote, setQuote] = useState<null | IChatMessage>(null);
   const focused = useWindowFocus();
+  const [userToDm, setUserToDm] = useState<null | UserToDM>(null);
   const [notifications, setNotifications] = useState<number>(0);
   const [messageLookup, setMessageLookup] = useState({});
   const addMessage = useCallback((message: IChatMessage) => {
@@ -73,11 +83,13 @@ export function ChatProvider({ children }: PropsWithChildren) {
     socket.current?.emit(ChatHandlers.SPEAK, {
       message: draft,
       quotes: quote?.id ?? null,
+      recipient: userToDm?.id ?? "",
     });
 
     setQuote(null);
     setDraft("");
-  }, [draft, quote]);
+    setUserToDm(null);
+  }, [draft, quote, userToDm]);
   const requestDeleteMessage = useCallback((withText: string) => {
     socket.current?.emit(ChatHandlers.DELETE, withText);
   }, []);
@@ -105,10 +117,12 @@ export function ChatProvider({ children }: PropsWithChildren) {
       draft,
       quote,
       messageLookup,
+      userToDm,
       quoteMessage,
       sendMessage,
       deleteMessage: requestDeleteMessage,
       updateDraft: setDraft,
+      updateUserToDm: setUserToDm,
     }),
     [
       online,
@@ -117,6 +131,7 @@ export function ChatProvider({ children }: PropsWithChildren) {
       draft,
       quote,
       messageLookup,
+      userToDm,
       sendMessage,
       deleteMessage,
       quoteMessage,
diff --git a/files/routes/chat.py b/files/routes/chat.py
index 398fae1cb..a70326ed2 100644
--- a/files/routes/chat.py
+++ b/files/routes/chat.py
@@ -6,10 +6,9 @@ from files.helpers.sanitize import sanitize
 from files.helpers.const import *
 from files.helpers.alerts import *
 from files.helpers.regex import *
-from datetime import datetime
 from flask_socketio import SocketIO, emit
 from files.__main__ import app, limiter, cache
-from flask import render_template, make_response, send_from_directory
+from flask import render_template
 import sys
 import atexit
 
@@ -33,6 +32,8 @@ cache.set(ONLINE_STR, len(online), timeout=0)
 muted = cache.get(f'{SITE}_muted') or {}
 messages = cache.get(f'{SITE}_chat') or []
 total = cache.get(f'{SITE}_total') or 0
+socket_ids_to_user_ids = {}
+user_ids_to_socket_ids = {}
 
 @app.get("/chat")
 @is_not_permabanned
@@ -60,11 +61,14 @@ def speak(data, v):
 	if not text: return '', 403
 	text_html = sanitize(text, count_marseys=True)
 	quotes = data['quotes']
+	recipient = data['recipient']
 	data={
 		"id": str(uuid.uuid4()),
 		"quotes": quotes,
 		"avatar": v.profile_url,
 		"hat": v.hat_active,
+		"user_id": v.id,
+		"dm": bool(recipient and recipient != ""),
 		"username": v.username,
 		"namecolor": v.name_color,
 		"text": text,
@@ -81,6 +85,9 @@ def speak(data, v):
 		v.shadowbanned = 'AutoJanny'
 		g.db.add(v)
 		send_repeatable_notification(CARP_ID, f"{v.username} has been shadowbanned because of a chat message.")
+	elif recipient and user_ids_to_socket_ids.get(recipient):
+		recipient_sid = user_ids_to_socket_ids[recipient]
+		emit('speak', data, broadcast=False, to=recipient_sid)
 	else:
 		emit('speak', data, broadcast=True)
 		messages.append(data)
@@ -106,6 +113,10 @@ def connect(v):
 		emit("online", online, broadcast=True)
 		cache.set(ONLINE_STR, len(online), timeout=0)
 
+	if not socket_ids_to_user_ids.get(request.sid):
+		socket_ids_to_user_ids[request.sid] = v.id
+		user_ids_to_socket_ids[v.id] = request.sid
+
 	emit('online', online)
 	emit('catchup', messages)
 	emit('typing', typing)
@@ -120,6 +131,11 @@ def disconnect(v):
 		cache.set(ONLINE_STR, len(online), timeout=0)
 
 	if v.username in typing: typing.remove(v.username)
+
+	if socket_ids_to_user_ids.get(request.sid):
+		del socket_ids_to_user_ids[request.sid]
+		del user_ids_to_socket_ids[v.id]
+
 	emit('typing', typing, broadcast=True)
 	return '', 204