diff --git a/src/components/ContentGenerator/ContentGenerator.tsx b/src/components/ContentGenerator/ContentGenerator.tsx
index bc255b931..5c5dd0a45 100644
--- a/src/components/ContentGenerator/ContentGenerator.tsx
+++ b/src/components/ContentGenerator/ContentGenerator.tsx
@@ -6,9 +6,6 @@ import {
 } from 'lucide-react';
 import { useEffect, useId, useState, type FormEvent } from 'react';
 import { FormatItem } from './FormatItem';
-import { GuideOptions } from './GuideOptions';
-import { FineTuneCourse } from '../GenerateCourse/FineTuneCourse';
-import { CourseOptions } from './CourseOptions';
 import {
   clearFineTuneData,
   getCourseFineTuneData,
@@ -20,9 +17,10 @@ import { showLoginPopup } from '../../lib/popup';
 import { UpgradeAccountModal } from '../Billing/UpgradeAccountModal';
 import { useIsPaidUser } from '../../queries/billing';
 import { cn } from '../../lib/classname';
+import { QuestionAnswerChat } from './QuestionAnswerChat';
 
 const allowedFormats = ['course', 'guide', 'roadmap'] as const;
-type AllowedFormat = (typeof allowedFormats)[number];
+export type AllowedFormat = (typeof allowedFormats)[number];
 
 export function ContentGenerator() {
   const [isUpgradeModalOpen, setIsUpgradeModalOpen] = useState(false);
@@ -145,7 +143,10 @@ export function ContentGenerator() {
             id={titleFieldId}
             placeholder="Enter a topic"
             value={title}
-            onChange={(e) => setTitle(e.target.value)}
+            onChange={(e) => {
+              setTitle(e.target.value);
+              setShowFineTuneOptions(false);
+            }}
             className="block w-full rounded-xl border border-gray-200 bg-white p-4 outline-none placeholder:text-gray-500 focus:border-gray-500"
             required
             minLength={3}
@@ -172,48 +173,21 @@ export function ContentGenerator() {
           </div>
         </div>
 
-        {selectedFormat === 'guide' && (
-          <GuideOptions depth={depth} setDepth={setDepth} />
-        )}
-
-        {selectedFormat === 'course' && (
-          <CourseOptions
-            difficulty={difficulty}
-            setDifficulty={setDifficulty}
+        <label
+          className="flex items-center gap-2 rounded-xl border border-gray-200 bg-white p-4"
+          htmlFor={fineTuneOptionsId}
+        >
+          <input
+            type="checkbox"
+            id={fineTuneOptionsId}
+            checked={showFineTuneOptions}
+            onChange={(e) => setShowFineTuneOptions(e.target.checked)}
           />
-        )}
+          Answer the following questions for a better {selectedFormat}
+        </label>
 
-        {selectedFormat !== 'roadmap' && (
-          <>
-            <label
-              className={cn(
-                'flex items-center gap-2 border border-gray-200 bg-white p-4',
-                showFineTuneOptions && 'rounded-t-xl',
-                !showFineTuneOptions && 'rounded-xl',
-              )}
-              htmlFor={fineTuneOptionsId}
-            >
-              <input
-                type="checkbox"
-                id={fineTuneOptionsId}
-                checked={showFineTuneOptions}
-                onChange={(e) => setShowFineTuneOptions(e.target.checked)}
-              />
-              Explain more for a better result
-            </label>
-            {showFineTuneOptions && (
-              <FineTuneCourse
-                hasFineTuneData={showFineTuneOptions}
-                about={about}
-                goal={goal}
-                customInstructions={customInstructions}
-                setAbout={setAbout}
-                setGoal={setGoal}
-                setCustomInstructions={setCustomInstructions}
-                className="-mt-4.5 overflow-hidden rounded-b-xl border border-gray-200 bg-white [&_div:first-child_label]:border-t-0"
-              />
-            )}
-          </>
+        {showFineTuneOptions && (
+          <QuestionAnswerChat term={title} format={selectedFormat} />
         )}
 
         <button
diff --git a/src/components/ContentGenerator/CourseOptions.tsx b/src/components/ContentGenerator/CourseOptions.tsx
deleted file mode 100644
index 6f6df4432..000000000
--- a/src/components/ContentGenerator/CourseOptions.tsx
+++ /dev/null
@@ -1,79 +0,0 @@
-import { useId, useState } from 'react';
-import {
-  Select,
-  SelectContent,
-  SelectItem,
-  SelectTrigger,
-  SelectValue,
-} from '../Select';
-
-type CourseOptionsProps = {
-  difficulty: string;
-  setDifficulty: (difficulty: string) => void;
-};
-
-export function CourseOptions(props: CourseOptionsProps) {
-  const { difficulty, setDifficulty } = props;
-  const difficultySelectId = useId();
-
-  const difficultyOptions = [
-    {
-      label: 'Beginner',
-      value: 'beginner',
-      description: 'Covers fundamental concepts',
-    },
-    {
-      label: 'Intermediate',
-      value: 'intermediate',
-      description: 'Explore advanced topics',
-    },
-    {
-      label: 'Advanced',
-      value: 'advanced',
-      description: 'Deep dives into complex concepts',
-    },
-  ];
-
-  const selectedDifficulty = difficultyOptions.find(
-    (option) => option.value === difficulty,
-  );
-
-  return (
-    <div className="flex flex-col gap-2">
-      <label
-        htmlFor={difficultySelectId}
-        className="inline-block text-gray-500"
-      >
-        Choose difficulty level
-      </label>
-      <Select value={difficulty} onValueChange={setDifficulty}>
-        <SelectTrigger
-          id={difficultySelectId}
-          className="h-auto rounded-xl bg-white p-4 text-base"
-        >
-          {selectedDifficulty && (
-            <div className="flex flex-col gap-1">
-              <span>{selectedDifficulty.label}</span>
-            </div>
-          )}
-
-          {!selectedDifficulty && (
-            <SelectValue placeholder="Select a difficulty" />
-          )}
-        </SelectTrigger>
-        <SelectContent className="rounded-xl bg-white">
-          {difficultyOptions.map((option) => (
-            <SelectItem key={option.value} value={option.value}>
-              <div className="flex flex-col gap-1">
-                <span>{option.label}</span>
-                <span className="text-xs text-gray-500">
-                  {option.description}
-                </span>
-              </div>
-            </SelectItem>
-          ))}
-        </SelectContent>
-      </Select>
-    </div>
-  );
-}
diff --git a/src/components/ContentGenerator/GuideOptions.tsx b/src/components/ContentGenerator/GuideOptions.tsx
deleted file mode 100644
index 4c7801239..000000000
--- a/src/components/ContentGenerator/GuideOptions.tsx
+++ /dev/null
@@ -1,72 +0,0 @@
-import { useId } from 'react';
-import {
-  Select,
-  SelectContent,
-  SelectItem,
-  SelectTrigger,
-  SelectValue,
-} from '../Select';
-
-type GuideOptionsProps = {
-  depth: string;
-  setDepth: (depth: string) => void;
-};
-
-export function GuideOptions(props: GuideOptionsProps) {
-  const { depth, setDepth } = props;
-  const depthSelectId = useId();
-
-  const depthOptions = [
-    {
-      label: 'Essentials',
-      value: 'essentials',
-      description: 'Just the core concepts',
-    },
-    {
-      label: 'Detailed',
-      value: 'detailed',
-      description: 'In-depth explanation',
-    },
-    {
-      label: 'Complete',
-      value: 'complete',
-      description: 'Cover the topic fully',
-    },
-  ];
-
-  const selectedDepth = depthOptions.find((option) => option.value === depth);
-
-  return (
-    <div className="flex flex-col gap-2">
-      <label htmlFor={depthSelectId} className="inline-block text-gray-500">
-        Choose depth of content
-      </label>
-      <Select value={depth} onValueChange={setDepth}>
-        <SelectTrigger
-          id={depthSelectId}
-          className="h-auto rounded-xl bg-white p-4 text-base"
-        >
-          {selectedDepth && (
-            <div className="flex flex-col gap-1">
-              <span>{selectedDepth.label}</span>
-            </div>
-          )}
-
-          {!selectedDepth && <SelectValue placeholder="Select a depth" />}
-        </SelectTrigger>
-        <SelectContent className="rounded-xl bg-white">
-          {depthOptions.map((option) => (
-            <SelectItem key={option.value} value={option.value}>
-              <div className="flex flex-col gap-1">
-                <span>{option.label}</span>
-                <span className="text-xs text-gray-500">
-                  {option.description}
-                </span>
-              </div>
-            </SelectItem>
-          ))}
-        </SelectContent>
-      </Select>
-    </div>
-  );
-}
diff --git a/src/components/ContentGenerator/QuestionAnswerChat.tsx b/src/components/ContentGenerator/QuestionAnswerChat.tsx
new file mode 100644
index 000000000..fc4503d4c
--- /dev/null
+++ b/src/components/ContentGenerator/QuestionAnswerChat.tsx
@@ -0,0 +1,241 @@
+import { useQuery } from '@tanstack/react-query';
+import { queryClient } from '../../stores/query-client';
+import { aiQuestionSuggestionsOptions } from '../../queries/user-ai-session';
+import type { AllowedFormat } from './ContentGenerator';
+import { Loader2Icon, SendIcon } from 'lucide-react';
+import { useRef, useState } from 'react';
+import { cn } from '../../lib/classname';
+import { flushSync } from 'react-dom';
+import { CheckIcon } from '../ReactIcons/CheckIcon';
+
+type QuestionAnswerChatProps = {
+  term: string;
+  format: AllowedFormat;
+};
+
+type QuestionAnswerChatMessage =
+  | { role: 'user'; answer: string }
+  | {
+      role: 'assistant';
+      question: string;
+      possibleAnswers: string[];
+    };
+
+export function QuestionAnswerChat(props: QuestionAnswerChatProps) {
+  const { term, format } = props;
+
+  const [questionAnswerChatMessages, setQuestionAnswerChatMessages] = useState<
+    QuestionAnswerChatMessage[]
+  >([]);
+  const [activeMessageIndex, setActiveMessageIndex] = useState(0);
+  const [message, setMessage] = useState('');
+  const [status, setStatus] = useState<'answering' | 'done'>('answering');
+
+  const scrollAreaRef = useRef<HTMLDivElement>(null);
+
+  const {
+    data: aiQuestionSuggestions,
+    isLoading: isLoadingAiQuestionSuggestions,
+  } = useQuery(aiQuestionSuggestionsOptions({ term, format }), queryClient);
+
+  const activeMessage = aiQuestionSuggestions?.questions[activeMessageIndex];
+
+  const scrollToBottom = () => {
+    if (!scrollAreaRef.current) {
+      return;
+    }
+
+    scrollAreaRef.current.scrollTo({
+      top: scrollAreaRef.current.scrollHeight,
+      behavior: 'instant',
+    });
+  };
+  const handleAnswerSelect = (answer: string) => {
+    const trimmedAnswer = answer.trim();
+    if (!activeMessage || !trimmedAnswer) {
+      return;
+    }
+
+    setQuestionAnswerChatMessages((prev) => {
+      return [
+        ...prev,
+        {
+          role: 'assistant',
+          ...activeMessage,
+        },
+        {
+          role: 'user',
+          answer: trimmedAnswer,
+        },
+      ];
+    });
+
+    setMessage('');
+
+    const hasMoreMessages =
+      activeMessageIndex < aiQuestionSuggestions.questions.length - 1;
+    if (!hasMoreMessages) {
+      setStatus('done');
+      return;
+    }
+
+    flushSync(() => {
+      setActiveMessageIndex(activeMessageIndex + 1);
+      setStatus('answering');
+    });
+
+    scrollToBottom();
+  };
+
+  const canGenerateNow =
+    // user can generate after answering 5 questions -> 5 * 2 messages (user and assistant)
+    !isLoadingAiQuestionSuggestions && questionAnswerChatMessages.length > 10;
+
+  return (
+    <>
+      <div className="relative h-[300px] w-full overflow-hidden rounded-xl border border-gray-200 bg-white">
+        {isLoadingAiQuestionSuggestions && (
+          <div className="absolute inset-0 flex items-center justify-center bg-white">
+            <div className="flex animate-pulse items-center gap-2 rounded-full border border-gray-200 bg-gray-50 p-2 px-4 text-sm">
+              <Loader2Icon className="size-4 animate-spin" />
+              <span>Generating personalized questions...</span>
+            </div>
+          </div>
+        )}
+
+        {!isLoadingAiQuestionSuggestions && status === 'done' && (
+          <div className="absolute inset-0 flex items-center justify-center bg-white">
+            <div className="flex flex-col items-center">
+              <CheckIcon additionalClasses="size-12" />
+              <p className="mt-3 text-lg">Preferences saved</p>
+              <p className="text-sm text-gray-500">
+                You can now start generating {format}
+              </p>
+            </div>
+          </div>
+        )}
+
+        {!isLoadingAiQuestionSuggestions && status === 'answering' && (
+          <div className="flex h-full w-full flex-col bg-white">
+            <div
+              ref={scrollAreaRef}
+              className="relative h-full w-full grow overflow-y-auto"
+            >
+              <div className="absolute inset-0 flex flex-col">
+                <div className="flex w-full grow flex-col justify-end gap-2 p-2">
+                  {questionAnswerChatMessages.map((message, index) => (
+                    <QuestionAnswerChatMessage
+                      key={index}
+                      role={message.role}
+                      question={
+                        message.role === 'assistant'
+                          ? message.question
+                          : undefined
+                      }
+                      answer={
+                        message.role === 'user' ? message.answer : undefined
+                      }
+                    />
+                  ))}
+
+                  <QuestionAnswerChatMessage
+                    role="assistant"
+                    question={activeMessage?.question ?? ''}
+                  />
+
+                  {activeMessage && (
+                    <div>
+                      <p className="text-sm text-gray-500">
+                        Pick an answer from these or write it below
+                      </p>
+                      <div className="mt-2 flex flex-wrap gap-2 text-sm text-gray-500">
+                        {activeMessage.possibleAnswers.map((answer) => (
+                          <button
+                            type="button"
+                            key={answer}
+                            className="cursor-pointer rounded-lg bg-gray-100 p-1 px-2 hover:bg-gray-200"
+                            onClick={() => {
+                              handleAnswerSelect(answer);
+                            }}
+                          >
+                            {answer}
+                          </button>
+                        ))}
+                      </div>
+                    </div>
+                  )}
+                </div>
+              </div>
+            </div>
+
+            <div className="p-2">
+              <div
+                className="flex w-full items-center justify-between gap-2 rounded-lg border border-gray-200 bg-white p-2"
+                onSubmit={(e) => {
+                  e.preventDefault();
+                  handleAnswerSelect(message);
+                }}
+              >
+                <input
+                  value={message}
+                  onChange={(e) => setMessage(e.target.value)}
+                  className="w-full bg-transparent text-sm focus:outline-none"
+                  placeholder="Write your answer here..."
+                  autoFocus
+                  onKeyDown={(e) => {
+                    if (e.key === 'Enter' && !e.shiftKey) {
+                      e.preventDefault();
+                      handleAnswerSelect(message);
+                      setMessage('');
+                    }
+                  }}
+                />
+
+                <button
+                  type="button"
+                  className="flex size-7 shrink-0 items-center justify-center rounded-md hover:bg-gray-100 disabled:cursor-not-allowed disabled:opacity-50"
+                >
+                  <SendIcon className="size-4" />
+                </button>
+              </div>
+            </div>
+          </div>
+        )}
+      </div>
+
+      {canGenerateNow && status !== 'done' && (
+        <div className="flex w-full items-center rounded-lg border border-gray-200 bg-white p-2">
+          <p className="text-sm">
+            Keep answering for better output or{' '}
+            <button className="text-blue-500 underline underline-offset-2 hover:no-underline focus:outline-none">
+              Generate now.
+            </button>
+          </p>
+        </div>
+      )}
+    </>
+  );
+}
+
+type QuestionAnswerChatMessageProps = {
+  role: 'user' | 'assistant';
+  question?: string;
+  answer?: string;
+};
+
+function QuestionAnswerChatMessage(props: QuestionAnswerChatMessageProps) {
+  const { role, question, answer } = props;
+
+  return (
+    <div
+      className={cn(
+        'flex w-fit items-center gap-2 rounded-lg border p-2 text-pretty',
+        role === 'user' && 'self-end border-gray-200 bg-gray-300/30',
+        role === 'assistant' && 'border-yellow-200 bg-yellow-300/30',
+      )}
+    >
+      {role === 'assistant' && <div className="text-sm">{question}</div>}
+      {role === 'user' && <div className="text-sm">{answer}</div>}
+    </div>
+  );
+}
diff --git a/src/queries/user-ai-session.ts b/src/queries/user-ai-session.ts
new file mode 100644
index 000000000..83157ec9e
--- /dev/null
+++ b/src/queries/user-ai-session.ts
@@ -0,0 +1,30 @@
+import { queryOptions } from '@tanstack/react-query';
+import { httpGet } from '../lib/query-http';
+
+type AIQuestionSuggestionsQuery = {
+  term: string;
+  format: string;
+};
+
+export type AIQuestionSuggestionsResponse = {
+  questions: {
+    question: string;
+    possibleAnswers: string[];
+  }[];
+};
+
+export function aiQuestionSuggestionsOptions(
+  query: AIQuestionSuggestionsQuery,
+) {
+  return queryOptions({
+    queryKey: ['ai-question-suggestions', query],
+    queryFn: () => {
+      return httpGet<AIQuestionSuggestionsResponse>(
+        `/v1-ai-question-suggestions`,
+        query,
+      );
+    },
+    enabled: !!query.term && !!query.format,
+    refetchOnMount: false,
+  });
+}