diff --git a/main.ts b/main.ts
index 81210f3..abb1802 100644
--- a/main.ts
+++ b/main.ts
@@ -44,7 +44,7 @@ app.use("/login", Express.static("public/login/login.html"));
 app.post("/join/dm/:nick", isLoggedIn, async (req, res) => {
   const nick = req.params.nick;
   var dms = await MongooseDal.getDirectMessagesForUser(UserSettings.nick, nick);
-  res.send({ nick: nick, messages: dms });
+  res.send({ nick: nick, messages: dms?.messages || [] });
 });
 
 app.post("/channel/join", isLoggedIn, async (req, res) => {
@@ -64,8 +64,6 @@ app.post("/channel/join", isLoggedIn, async (req, res) => {
   };
 
   var channelMessages = await MongooseDal.getMessagesForChannel(req.body.channel);
-  
-
   await MongooseDal.createChannel(channelMongo);
 
   channel.updateUsers(() => {
diff --git a/models/channel.ts b/models/channel.ts
index 6b1b8b8..e6cc07c 100644
--- a/models/channel.ts
+++ b/models/channel.ts
@@ -6,10 +6,10 @@ interface IMessage {
     created_at: Date;
 }
 
-interface IDirectMessage {
-    sender: string;
+interface IDirectMessages {
     owner: string;
-    message: string;
+    external_user: string;
+    messages: Array<IMessage>;
     created_at: Date;
 }
 
@@ -35,14 +35,14 @@ const channelSchema = new Schema<IChannel>({
     active: { type: Boolean, default: true }
 });
 
-const directMessageSchema = new Schema<IDirectMessage>({
+const directMessageSchema = new Schema<IDirectMessages>({
     owner: { type: String, required: true },
-    sender: { type: String, required: true },
-    message: { type: String, required: true },
+    external_user: { type: String, required: true },
+    messages: { type: [new Schema<IMessage>({ sender: String, message: String, created_at: { type: Date, default: Date.now } })], default: [] },
     created_at: { type: Date, default: Date.now }
 });
 
 const Channel = model<IChannel>('Channel', channelSchema);
-const DirectMessage = model<IDirectMessage>('DirectMessage', directMessageSchema);
+const DirectMessages = model<IDirectMessages>('DirectMessages', directMessageSchema);
 
-export { Channel, DirectMessage, IChannel, IMessage, IDirectMessage };
\ No newline at end of file
+export { Channel, DirectMessages, IChannel, IMessage, IDirectMessages };
\ No newline at end of file
diff --git a/public/login/login.html b/public/login/login.html
index 61015d1..8dc5355 100644
--- a/public/login/login.html
+++ b/public/login/login.html
@@ -42,7 +42,7 @@ <h1 class="text-xl mb-8">Login</h1>
         var password = document.getElementById('password').value;
 
         // POST with axios to /login
-        axios.post('/user/login', {
+        axios.post('http://127.0.0.1:3000/user/login', {
             username: username,
             password: password
         }).then((response) => {
diff --git a/public/main.js b/public/main.js
index fbd57f0..6d6a3d0 100644
--- a/public/main.js
+++ b/public/main.js
@@ -143,8 +143,12 @@ socket.on('channel:list', function (data) {
 socket.on('channel:parted', function (data) {
     $('#users').empty();
     $('#messages').empty();
+    // Sort the users by their modes
+    data.users.sort((a, b) => (a.modes > b.modes ? 1 : -1));
     $.each(data.users, function (index, user) {
-        $('#users').append('<li class="flex items-center space-x-4"><i class="fas fa-user"></i><span class="text-sm font-medium">' + user.nick + ' [' + user.modes + ']</span></li>');
+        $('#users').append('<li class="flex items-center space-x-4"onclick="openDirectMessage(\'' 
+            + user.user + '\')"><i class="fas fa-user"></i><span class="text-sm font-medium">' 
+            + user.nick + ' [' + user.modes + ']</span></li>');
     });
     $('#channel_name').text('ChanServe');
     selectedChannel = 'ChanServe';
@@ -152,11 +156,18 @@ socket.on('channel:parted', function (data) {
 });
 
 socket.on('channel:joined', function (data) {
+    if(!data.users || data.users.length <= 1){
+        openDirectMessage(data.channel);
+        return;
+    }
     data.channel[0] == '#' ? selectedChannel = data.channel.substring(1) : selectedChannel = data.channel;
     $('#users').empty();
     $('#messages').empty();
+    data.users.sort((a, b) => (a.modes > b.modes ? 1 : -1));
     $.each(data.users, function (index, user) {
-        $('#users').append('<li class="flex items-center space-x-4"><i class="fas fa-user"></i><span class="text-sm font-medium">' + user.nick + ' [' + user.modes + ']</span></li>');
+        $('#users').append('<li class="flex items-center space-x-4"onclick="openDirectMessage(\'' 
+            + user.nick + '\')"><i class="fas fa-user"></i><span class="text-sm font-medium">' 
+            + user.nick + ' [' + user.modes + ']</span></li>');
     });
     // add to channels if not exists
     if(!channels.filter(channel => channel.name == data.channel).length > 0){
diff --git a/services/mongo.ts b/services/mongo.ts
index 64a38a0..060bac1 100644
--- a/services/mongo.ts
+++ b/services/mongo.ts
@@ -1,6 +1,6 @@
 // Mongoose controller
 import mongoose from "mongoose";
-import { Channel, DirectMessage, IChannel, IMessage, IDirectMessage } from "../models/channel";
+import { Channel, DirectMessages, IChannel, IMessage } from "../models/channel";
 import { MessageQueue, IMessageQueue } from "../models/messageQueue";
 
 // MONGODB MONGOOS DAL CLASS
@@ -31,10 +31,6 @@ const MongooseDal = {
 
         return Channel.updateOne( { name: channelName }, { $push: { messages: message }, updated_at: new Date() });
     },
-    addDirectMessage: async (message: IDirectMessage) => {
-        console.log(message);
-        return await DirectMessage.create(message);
-    },
     getChannelsForUser: async (username: string) => {
        return await Channel.find({ owner: username, active: true }, { name: 1, updated_at: 1 });
     },
@@ -42,8 +38,16 @@ const MongooseDal = {
         var messages =  await Channel.findOne({ name: channelName }, { messages: 1 });
         return messages;
     },
-    getDirectMessagesForUser: async (owner: string, sender: string) => {
-        return await DirectMessage.find({ owner, sender });
+    getDirectMessagesForUser: async (owner: string, external_user: string) => {
+        return await DirectMessages.findOne({ owner, external_user }, { messages: 1 });
+    },
+    addDirectMessage: async (owner:string, external_user:string, message:IMessage) => {
+        const directMessage = await DirectMessages.findOne({ owner, external_user });
+        if (!directMessage) {
+            return await DirectMessages.create({ owner, external_user, messages: [message] });
+        } else {
+            return await DirectMessages.updateOne({ owner, external_user }, { $push: { messages: message } });
+        }
     },
     addMessageToQueue: async (message: IMessageQueue) => {
         return await MessageQueue.create(message);
diff --git a/services/socket.ts b/services/socket.ts
index d00744a..c3a3ae5 100644
--- a/services/socket.ts
+++ b/services/socket.ts
@@ -1,6 +1,6 @@
 import { Client } from "irc-framework";
 import { Server } from "socket.io";
-import { IDirectMessage, IMessage } from "../models/channel";
+import { IDirectMessages, IMessage } from "../models/channel";
 import UserSettings from "../config";
 import MongooseDal from "./mongo";
 import Utils from "./utils";
@@ -52,15 +52,14 @@ export class SocketService {
 
       // Direct Message
       socket.on("client:direct", async (message) => {
-        const directMessage: IDirectMessage = {
-          sender: message.from,
-          owner: message.to,
-          message: message.message,
-          created_at: new Date(),
-        };
-
-        await MongooseDal.addDirectMessage(directMessage);
-        this.ircClient.say(message.to, message.message);
+        const owner = UserSettings.nick; // TODO : get session user
+        const directMessage: IMessage = {
+            sender: owner,
+            message: message.message,
+            created_at: new Date(),
+          };
+          await MongooseDal.addDirectMessage(owner, message.to, directMessage);
+          this.ircClient.say(message.to, message.message);
       });
 
     });
@@ -84,14 +83,13 @@ export class SocketService {
   }
 
   async sendDirectMessageAsync(message: string, nick: string) {
-    const directMessage: IDirectMessage = {
-      sender: nick,
-      owner: UserSettings.nick,
-      message: message,
-      created_at: new Date(),
-    };
-
-    await MongooseDal.addDirectMessage(directMessage);
+    const owner = UserSettings.nick; // TODO : get session user
+    const directMessage: IMessage = {
+        sender: nick,
+        message: message,
+        created_at: new Date(),
+      };
+      await MongooseDal.addDirectMessage(owner, nick, directMessage);
 
     console.log("sending direct message to " + nick);
     this.io.emit("chat:direct", {