diff --git a/src/interface/desktop/chat.html b/src/interface/desktop/chat.html
index 391160fc..ecd8ebf9 100644
--- a/src/interface/desktop/chat.html
+++ b/src/interface/desktop/chat.html
@@ -386,6 +386,9 @@
             let chatInput = document.getElementById("chat-input");
             chatInput.value = chatInput.value.trimStart();
 
+            let questionStarterSuggestions = document.getElementById("question-starters");
+            questionStarterSuggestions.style.display = "none";
+
             if (chatInput.value.startsWith("/") && chatInput.value.split(" ").length === 1) {
                 let chatTooltip = document.getElementById("chat-tooltip");
                 chatTooltip.style.display = "block";
@@ -468,6 +471,31 @@
                     return;
                 });
 
+            fetch(`${hostURL}/api/chat/starters?client=desktop`, { headers })
+                .then(response => response.json())
+                .then(data => {
+                    // Render chat options, if any
+                    if (data) {
+                        let questionStarterSuggestions = document.getElementById("question-starters");
+                        for (let index in data) {
+                            let questionStarter = data[index];
+                            let questionStarterButton = document.createElement('button');
+                            questionStarterButton.innerHTML = questionStarter;
+                            questionStarterButton.classList.add("question-starter");
+                            questionStarterButton.addEventListener('click', function() {
+                                questionStarterSuggestions.style.display = "none";
+                                document.getElementById("chat-input").value = questionStarter;
+                                chat();
+                            });
+                            questionStarterSuggestions.appendChild(questionStarterButton);
+                        }
+                        questionStarterSuggestions.style.display = "grid";
+                    }
+                })
+                .catch(err => {
+                    return;
+                });
+
             fetch(`${hostURL}/api/chat/options`, { headers })
                 .then(response => response.json())
                 .then(data => {
@@ -507,6 +535,9 @@
         <!-- Chat Body -->
         <div id="chat-body"></div>
 
+        <!-- Chat Suggestions -->
+        <div id="question-starters" style="display: none;"></div>
+
         <!-- Chat Footer -->
         <div id="chat-footer">
             <div id="chat-tooltip" style="display: none;"></div>
@@ -684,6 +715,28 @@
             margin: 10px;
         }
 
+        div#question-starters {
+            grid-template-columns: repeat(auto-fit, minmax(100px, 1fr));
+            grid-column-gap: 8px;
+        }
+
+        button.question-starter {
+            background: var(--background-color);
+            color: var(--main-text-color);
+            border: 1px solid var(--main-text-color);
+            border-radius: 5px;
+            padding: 5px;
+            font-size: 14px;
+            font-weight: 300;
+            line-height: 1.5em;
+            cursor: pointer;
+            transition: background 0.2s ease-in-out;
+            text-align: left;
+            max-height: 75px;
+            transition: max-height 0.3s ease-in-out;
+            overflow: hidden;
+        }
+
         code.chat-response {
             background: var(--primary-hover);
             color: var(--primary-inverse);
diff --git a/src/khoj/database/adapters/__init__.py b/src/khoj/database/adapters/__init__.py
index 0a263ed4..7fd04006 100644
--- a/src/khoj/database/adapters/__init__.py
+++ b/src/khoj/database/adapters/__init__.py
@@ -1,9 +1,9 @@
 import math
+import random
 import secrets
 from datetime import date, datetime, timezone
 from typing import List, Optional, Type
 
-# Import sync_to_async from Django Channels
 from asgiref.sync import sync_to_async
 from django.contrib.sessions.backends.db import SessionStore
 from django.db import models
@@ -28,6 +28,9 @@ from khoj.database.models import (
     SearchModelConfig,
     Subscription,
     UserConversationConfig,
+    OpenAIProcessorConversationConfig,
+    OfflineChatProcessorConversationConfig,
+    ReflectiveQuestion,
 )
 from khoj.search_filter.date_filter import DateFilter
 from khoj.search_filter.file_filter import FileFilter
@@ -337,6 +340,25 @@ class ConversationAdapters:
     async def get_openai_chat_config():
         return await OpenAIProcessorConversationConfig.objects.filter().afirst()
 
+    @staticmethod
+    async def aget_conversation_starters(user: KhojUser):
+        all_questions = []
+        if await ReflectiveQuestion.objects.filter(user=user).aexists():
+            all_questions = await sync_to_async(ReflectiveQuestion.objects.filter(user=user).values_list)(
+                "question", flat=True
+            )
+
+        all_questions = await sync_to_async(ReflectiveQuestion.objects.filter(user=None).values_list)(
+            "question", flat=True
+        )
+
+        max_results = 3
+        all_questions = await sync_to_async(list)(all_questions)
+        if len(all_questions) < max_results:
+            return all_questions
+
+        return random.sample(all_questions, max_results)
+
     @staticmethod
     def get_valid_conversation_config(user: KhojUser):
         offline_chat_config = ConversationAdapters.get_offline_chat_conversation_config()
diff --git a/src/khoj/database/migrations/0020_reflectivequestion.py b/src/khoj/database/migrations/0020_reflectivequestion.py
new file mode 100644
index 00000000..aefb73bf
--- /dev/null
+++ b/src/khoj/database/migrations/0020_reflectivequestion.py
@@ -0,0 +1,36 @@
+# Generated by Django 4.2.7 on 2023-11-20 01:13
+
+from django.conf import settings
+from django.db import migrations, models
+import django.db.models.deletion
+
+
+class Migration(migrations.Migration):
+    dependencies = [
+        ("database", "0019_alter_googleuser_family_name_and_more"),
+    ]
+
+    operations = [
+        migrations.CreateModel(
+            name="ReflectiveQuestion",
+            fields=[
+                ("id", models.BigAutoField(auto_created=True, primary_key=True, serialize=False, verbose_name="ID")),
+                ("created_at", models.DateTimeField(auto_now_add=True)),
+                ("updated_at", models.DateTimeField(auto_now=True)),
+                ("question", models.CharField(max_length=500)),
+                (
+                    "user",
+                    models.ForeignKey(
+                        blank=True,
+                        default=None,
+                        null=True,
+                        on_delete=django.db.models.deletion.CASCADE,
+                        to=settings.AUTH_USER_MODEL,
+                    ),
+                ),
+            ],
+            options={
+                "abstract": False,
+            },
+        ),
+    ]
diff --git a/src/khoj/database/models/__init__.py b/src/khoj/database/models/__init__.py
index 92da3e6e..b0463df8 100644
--- a/src/khoj/database/models/__init__.py
+++ b/src/khoj/database/models/__init__.py
@@ -141,6 +141,11 @@ class Conversation(BaseModel):
     conversation_log = models.JSONField(default=dict)
 
 
+class ReflectiveQuestion(BaseModel):
+    question = models.CharField(max_length=500)
+    user = models.ForeignKey(KhojUser, on_delete=models.CASCADE, default=None, null=True, blank=True)
+
+
 class Entry(BaseModel):
     class EntryType(models.TextChoices):
         IMAGE = "image"
diff --git a/src/khoj/interface/web/chat.html b/src/khoj/interface/web/chat.html
index 7afa7bee..abab83ab 100644
--- a/src/khoj/interface/web/chat.html
+++ b/src/khoj/interface/web/chat.html
@@ -153,8 +153,8 @@ To get started, just start typing below. You can also type / to see a list of co
                     numOnlineReferences += onlineReference.organic.length;
                     for (let index in onlineReference.organic) {
                         let reference = onlineReference.organic[index];
-                    let polishedReference = generateOnlineReference(reference, index);
-                    referenceSection.appendChild(polishedReference);
+                        let polishedReference = generateOnlineReference(reference, index);
+                        referenceSection.appendChild(polishedReference);
                     }
                 }
 
@@ -162,8 +162,8 @@ To get started, just start typing below. You can also type / to see a list of co
                     numOnlineReferences += onlineReference.knowledgeGraph.length;
                     for (let index in onlineReference.knowledgeGraph) {
                         let reference = onlineReference.knowledgeGraph[index];
-                    let polishedReference = generateOnlineReference(reference, index);
-                    referenceSection.appendChild(polishedReference);
+                        let polishedReference = generateOnlineReference(reference, index);
+                        referenceSection.appendChild(polishedReference);
                     }
                 }
 
@@ -426,6 +426,9 @@ To get started, just start typing below. You can also type / to see a list of co
             let chatInput = document.getElementById("chat-input");
             chatInput.value = chatInput.value.trimStart();
 
+            let questionStarterSuggestions = document.getElementById("question-starters");
+            questionStarterSuggestions.style.display = "none";
+
             if (chatInput.value.startsWith("/") && chatInput.value.split(" ").length === 1) {
                 let chatTooltip = document.getElementById("chat-tooltip");
                 chatTooltip.style.display = "block";
@@ -505,6 +508,31 @@ To get started, just start typing below. You can also type / to see a list of co
                     return;
                 });
 
+            fetch('/api/chat/starters')
+                .then(response => response.json())
+                .then(data => {
+                    // Render chat options, if any
+                    if (data) {
+                        let questionStarterSuggestions = document.getElementById("question-starters");
+                        for (let index in data) {
+                            let questionStarter = data[index];
+                            let questionStarterButton = document.createElement('button');
+                            questionStarterButton.innerHTML = questionStarter;
+                            questionStarterButton.classList.add("question-starter");
+                            questionStarterButton.addEventListener('click', function() {
+                                questionStarterSuggestions.style.display = "none";
+                                document.getElementById("chat-input").value = questionStarter;
+                                chat();
+                            });
+                            questionStarterSuggestions.appendChild(questionStarterButton);
+                        }
+                        questionStarterSuggestions.style.display = "grid";
+                    }
+                })
+                .catch(err => {
+                    return;
+                });
+
             // Fill query field with value passed in URL query parameters, if any.
             var query_via_url = new URLSearchParams(window.location.search).get("q");
             if (query_via_url) {
@@ -524,6 +552,9 @@ To get started, just start typing below. You can also type / to see a list of co
         <!-- Chat Body -->
         <div id="chat-body"></div>
 
+        <!-- Chat Suggestions -->
+        <div id="question-starters" style="display: none;"></div>
+
         <!-- Chat Footer -->
         <div id="chat-footer">
             <div id="chat-tooltip" style="display: none;"></div>
@@ -584,6 +615,28 @@ To get started, just start typing below. You can also type / to see a list of co
             margin: 10px;
         }
 
+        div#question-starters {
+            grid-template-columns: repeat(auto-fit, minmax(100px, 1fr));
+            grid-column-gap: 8px;
+        }
+
+        button.question-starter {
+            background: var(--background-color);
+            color: var(--main-text-color);
+            border: 1px solid var(--main-text-color);
+            border-radius: 5px;
+            padding: 5px;
+            font-size: 14px;
+            font-weight: 300;
+            line-height: 1.5em;
+            cursor: pointer;
+            transition: background 0.2s ease-in-out;
+            text-align: left;
+            max-height: 75px;
+            transition: max-height 0.3s ease-in-out;
+            overflow: hidden;
+        }
+
         button.reference-button {
             background: var(--background-color);
             color: var(--main-text-color);
diff --git a/src/khoj/routers/api.py b/src/khoj/routers/api.py
index 1b90127b..83955088 100644
--- a/src/khoj/routers/api.py
+++ b/src/khoj/routers/api.py
@@ -512,6 +512,17 @@ def update(
     return {"status": "ok", "message": "khoj reloaded"}
 
 
+@api.get("/chat/starters", response_class=Response)
+@requires(["authenticated"])
+async def chat_starters(
+    request: Request,
+    common: CommonQueryParams,
+) -> Response:
+    user: KhojUser = request.user.object
+    starter_questions = await ConversationAdapters.aget_conversation_starters(user)
+    return Response(content=json.dumps(starter_questions), media_type="application/json", status_code=200)
+
+
 @api.get("/chat/history")
 @requires(["authenticated"])
 def chat_history(