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diff --git a/api/routes/__pycache__/auth_routes.cpython-311.pyc b/api/routes/__pycache__/auth_routes.cpython-311.pyc
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diff --git a/api/routes/__pycache__/conversation_routes.cpython-311.pyc b/api/routes/__pycache__/conversation_routes.cpython-311.pyc
index 1819319..94c2905 100644
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diff --git a/api/routes/conversation_routes.py b/api/routes/conversation_routes.py
index 1486be2..95783c0 100644
--- a/api/routes/conversation_routes.py
+++ b/api/routes/conversation_routes.py
@@ -1,9 +1,9 @@
+from typing import List
 from fastapi import APIRouter, Depends, HTTPException
 from fastapi.responses import StreamingResponse
 from pydantic import BaseModel
 from api.models.conversation import Message
-from api.utils.conversation_utils import create_conversation, add_message, get_conversation_by_id, rename_conversation, get_conversations_by_user, update_conversation_model
-from api.utils.llm_providers.openai import openai_generate_response
+from api.utils.conversation_utils import update_conversation_messages, create_conversation, add_message, get_conversation_by_id, get_conversations_by_user, update_conversation_model
 from api.utils.llm_utils import generate_response_stream
 from api.utils.auth_utils import get_current_user
 from api.models.user import User
@@ -40,6 +40,18 @@ async def add_message_route(conversation_id: str, message_create: MessageCreate,
     else:
         raise HTTPException(status_code=404, detail="Conversation not found")
 
+@router.put("/conversations/{conversation_id}/messages")
+async def update_messages_route(
+    conversation_id: str,
+    updated_messages: List[Message],
+    current_user: User = Depends(get_current_user),
+):
+    success = await update_conversation_messages(conversation_id, updated_messages, current_user.email)
+    if success:
+        return {"message": "Messages updated successfully"}
+    else:
+        raise HTTPException(status_code=404, detail="Conversation not found")
+
 @router.patch("/conversations/{conversation_id}")
 async def update_conversation_route(
     conversation_id: str,
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diff --git a/api/utils/__pycache__/conversation_utils.cpython-311.pyc b/api/utils/__pycache__/conversation_utils.cpython-311.pyc
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diff --git a/api/utils/__pycache__/db_utils.cpython-311.pyc b/api/utils/__pycache__/db_utils.cpython-311.pyc
index 50f6e3f..d5aa821 100644
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diff --git a/api/utils/__pycache__/llm_utils.cpython-311.pyc b/api/utils/__pycache__/llm_utils.cpython-311.pyc
index 7fe6921..b936cb2 100644
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diff --git a/api/utils/conversation_utils.py b/api/utils/conversation_utils.py
index 0a8bca2..6e8f06d 100644
--- a/api/utils/conversation_utils.py
+++ b/api/utils/conversation_utils.py
@@ -1,4 +1,6 @@
 from datetime import datetime, timezone
+from typing import List
+
 from api.utils.db_utils import get_db
 from api.models.conversation import Message, Conversation, LanguageModel
 from bson import ObjectId
@@ -74,4 +76,17 @@ async def update_conversation_model(conversation_id: str, model_provider: str, m
                 {"$set": update_fields}
             )
             return result.modified_count > 0
-    return False
\ No newline at end of file
+    return False
+
+async def update_conversation_messages(conversation_id: str, updated_messages: List[Message], user_email: str):
+    db = await get_db()
+    conversations_collection = db["conversations"]
+    conversation = await get_conversation_by_id(conversation_id, user_email)
+    if conversation:
+        await conversations_collection.update_one(
+            {"_id": ObjectId(conversation_id)},
+            {"$set": {"messages": [message.dict() for message in updated_messages]}},
+        )
+        return True
+    else:
+        return False
\ No newline at end of file
diff --git a/api/utils/llm_utils.py b/api/utils/llm_utils.py
index 4cf9a05..4c7bc2a 100644
--- a/api/utils/llm_utils.py
+++ b/api/utils/llm_utils.py
@@ -5,6 +5,8 @@
 from api.utils.llm_providers.anthropic import anthropic_generate_response, generate_conversation_name
 
 async def generate_response_stream(conversation):
+    visible_messages = [message for message in conversation.messages if not message.hidden]
+    conversation.messages = visible_messages    
     collected_chunks = []
     if conversation.model.provider == "openai":
         async for chunk in openai_generate_response(conversation):
diff --git a/app/components/ConversationMessages.tsx b/app/components/ConversationMessages.tsx
index c1d82ae..7b2d4c5 100644
--- a/app/components/ConversationMessages.tsx
+++ b/app/components/ConversationMessages.tsx
@@ -1,5 +1,5 @@
 import React, { useEffect, useRef } from "react";
-import { Box, Text, VStack } from "@chakra-ui/react";
+import { Box, Text, VStack, Button } from "@chakra-ui/react";
 import ReactMarkdown from "react-markdown";
 import remarkGfm from "remark-gfm";
 import remarkMath from "remark-math";
@@ -12,10 +12,12 @@ import { Components } from "react-markdown";
 export interface Message {
   role: "user" | "assistant";
   content: string;
+  hidden?: boolean;
 }
 
 interface ConversationMessagesProps {
   messages: Message[];
+  handleHideMessage: (index: number) => Promise<void>;
   userName?: string;
 }
 
@@ -27,6 +29,7 @@ type MathComponents = {
 
 const ConversationMessages: React.FC<ConversationMessagesProps> = ({
   messages,
+  handleHideMessage,
   userName = "User",
 }) => {
   const messagesEndRef = useRef<HTMLDivElement>(null);
@@ -43,11 +46,15 @@ const ConversationMessages: React.FC<ConversationMessagesProps> = ({
           borderRadius="none"
           borderWidth="1px"
           p={4}
-          borderColor="black"
+          borderColor={message.hidden ? "gray.300" : "black"}
           alignSelf={message.role === "user" ? "flex-end" : "flex-start"}
           maxWidth="100%"
         >
-          <Text fontWeight="bold" mb={1}>
+          <Text
+            fontWeight="bold"
+            mb={1}
+            color={message.hidden ? "gray.500" : "inherit"}
+          >
             [{index}] {message.role === "user" ? userName : "Assistant"}
           </Text>
           <ReactMarkdown
@@ -87,6 +94,15 @@ const ConversationMessages: React.FC<ConversationMessagesProps> = ({
           >
             {message.content}
           </ReactMarkdown>
+          <Button
+            size="xs"
+            variant="ghost"
+            onClick={() => handleHideMessage(index)}
+            ml="auto"
+            mt={2}
+          >
+            hide
+          </Button>
         </Box>
       ))}
       <div ref={messagesEndRef} />
diff --git a/app/components/Sidebar.tsx b/app/components/Sidebar.tsx
index ff5ca44..3ab0f77 100644
--- a/app/components/Sidebar.tsx
+++ b/app/components/Sidebar.tsx
@@ -9,8 +9,9 @@ import {
   DrawerOverlay,
   useDisclosure,
   IconButton,
+  Text,
+  Divider,
 } from "@chakra-ui/react";
-
 import { ChevronRightIcon } from "@chakra-ui/icons";
 import { ConversationInfo } from "../utils";
 
@@ -19,14 +20,34 @@ interface SidebarProps {
   setConversationId: (id: string) => void;
 }
 
+const handleConversationClick = (
+  id: string,
+  setConversationId: (id: string) => void,
+  onClose: () => void
+) => {
+  setConversationId(id);
+  onClose();
+};
+
 const Sidebar = ({ conversations, setConversationId }: SidebarProps) => {
   const { isOpen, onOpen, onClose } = useDisclosure();
 
-  const handleConversationClick = (id: string) => {
-    setConversationId(id);
-    onClose();
+  const groupConversationsByDate = (conversations: ConversationInfo[]) => {
+    const groupedConversations: Record<string, ConversationInfo[]> = {};
+
+    conversations.forEach((conversation) => {
+      const date = new Date(conversation.created_at).toDateString();
+      if (!groupedConversations[date]) {
+        groupedConversations[date] = [];
+      }
+      groupedConversations[date].push(conversation);
+    });
+
+    return groupedConversations;
   };
 
+  const groupedConversations = groupConversationsByDate(conversations);
+
   return (
     <>
       <IconButton
@@ -39,31 +60,57 @@ const Sidebar = ({ conversations, setConversationId }: SidebarProps) => {
         variant="ghost"
         height="100px"
       />
-      <Drawer isOpen={isOpen} onClose={onClose} placement="left" >
-        {/* <DrawerOverlay> */}
-        <DrawerContent>
-          <DrawerBody>
-            <Box w="100%" h="100vh" bg="white">
-              <VStack w="100%" align="stretch" spacing={1} pt={5}>
-                {conversations.map((conversation) => (
-                  <Button
-                    paddingLeft={2}
-                    justifyContent="flex-start"
-                    key={conversation.id}
-                    variant="ghost"
-                    borderRadius="none"
-                    pr={0}
-                    height={8}
-                    onClick={() => handleConversationClick(conversation.id)}
-                  >
-                    {conversation.name}
-                  </Button>
-                ))}
-              </VStack>
-            </Box>
-          </DrawerBody>
-        </DrawerContent>
-        {/* </DrawerOverlay> */}
+      <Drawer isOpen={isOpen} onClose={onClose} placement="left">
+        <DrawerOverlay>
+          <DrawerContent>
+            <DrawerBody>
+              <Box w="100%" h="100vh" bg="white">
+                <VStack w="100%" align="stretch" spacing={1} pt={5}>
+                  {Object.entries(groupedConversations).map(
+                    ([date, conversationsOnDate]) => (
+                      <Box key={date}>
+                        <Text fontSize="xs" fontWeight="semibold" ml={2} mb={1}>
+                          {date}
+                        </Text>
+                        {conversationsOnDate.map((conversation) => (
+                          <Button
+                            key={conversation.id}
+                            paddingLeft={4}
+                            justifyContent="flex-start"
+                            variant="ghost"
+                            borderRadius="none"
+                            pr={0}
+                            height={8}
+                            width='200px'
+                            onClick={() =>
+                              handleConversationClick(
+                                conversation.id,
+                                setConversationId,
+                                onClose
+                              )
+                            }
+                          >
+                            <Text
+                              fontSize="sm"
+                              fontWeight="semibold"
+                              whiteSpace="nowrap"
+                              overflow="hidden"
+                              textOverflow="ellipsis"
+                              maxW="200px"
+                            >
+                              {conversation.name}
+                            </Text>
+                          </Button>
+                        ))}
+                        <Divider />
+                      </Box>
+                    )
+                  )}
+                </VStack>
+              </Box>
+            </DrawerBody>
+          </DrawerContent>
+        </DrawerOverlay>
       </Drawer>
     </>
   );
diff --git a/app/page.tsx b/app/page.tsx
index 6c23d54..6be55f3 100644
--- a/app/page.tsx
+++ b/app/page.tsx
@@ -48,6 +48,30 @@ export default function Home() {
     setTextValue(event.target.value);
   };
 
+  const handleHideMessage = async (index: number) => {
+    try {
+      const updatedMessages = messages.map((msg, i) =>
+        i === index ? { ...msg, hidden: !msg.hidden } : msg
+      );
+      await fetch(
+        `${process.env.BACKEND_URL}/conversations/${conversationId}/messages`,
+        {
+          method: "PUT",
+          headers: {
+            "Content-Type": "application/json",
+            Authorization: `Bearer ${cookies.token}`,
+          },
+          body: JSON.stringify({ messages: updatedMessages }),
+          mode: "cors",
+          credentials: "include",
+        }
+      );
+      setMessages(updatedMessages);
+    } catch (error) {
+      console.error("Error toggling message visibility:", error);
+    }
+  };
+
   useEffect(() => {
     const token = searchParams.get("token");
 
@@ -139,7 +163,10 @@ export default function Home() {
           justify="space-between"
         >
           <Box width="100%" pt={2} pb={2}>
-            <ConversationMessages messages={messages} />
+            <ConversationMessages
+              messages={messages}
+              handleHideMessage={handleHideMessage}
+            />
           </Box>
         </VStack>
       </Center>