diff --git a/apps/admin/src/components/ai/AiGeneratorDialog.tsx b/apps/admin/src/components/ai/AiGeneratorDialog.tsx
index e64d3a1..18156f3 100644
--- a/apps/admin/src/components/ai/AiGeneratorDialog.tsx
+++ b/apps/admin/src/components/ai/AiGeneratorDialog.tsx
@@ -26,6 +26,7 @@ interface AiGeneratorDialogProps {
         packDescription?: string | null;
         existingCategories?: string[];
         existingPacks?: string[];
+        existingQuestions?: string[];
         isExplicit?: boolean;
     };
     onGenerated: (result: any) => void;
@@ -71,7 +72,7 @@ export function AiGeneratorDialog({
                     toast.error('Pack name is required');
                     return;
                 }
-                const result = await generateQuestions(context.packName, count, undefined, tone, context.packDescription || undefined);
+                const result = await generateQuestions(context.packName, count, undefined, tone, context.packDescription || undefined, context.existingQuestions);
                 setGeneratedQuestions(result);
                 // Select all questions by default
                 setSelectedQuestionIndices(new Set(result.map((_, i) => i)));
diff --git a/apps/admin/src/components/ui/emoji-picker.tsx b/apps/admin/src/components/ui/emoji-picker.tsx
index b3d7982..4ded99c 100644
--- a/apps/admin/src/components/ui/emoji-picker.tsx
+++ b/apps/admin/src/components/ui/emoji-picker.tsx
@@ -1,5 +1,5 @@
 import { useState, useRef, useEffect } from 'react';
-import data from '@emoji-mart/data';
+import * as data from '@emoji-mart/data';
 import Picker from '@emoji-mart/react';
 import { Button } from './button';
 
diff --git a/apps/admin/src/lib/openai.ts b/apps/admin/src/lib/openai.ts
index b163380..c409d46 100644
--- a/apps/admin/src/lib/openai.ts
+++ b/apps/admin/src/lib/openai.ts
@@ -194,7 +194,8 @@ export async function generateQuestions(
     count: number = 10,
     intensity?: number,
     tone: ToneLevel = 3,
-    packDescription?: string
+    packDescription?: string,
+    existingQuestions?: string[]
 ): Promise<GeneratedQuestion[]> {
     const openai = getOpenAI();
     const isClean = tone === 0;
@@ -246,7 +247,14 @@ export async function generateQuestions(
         ? `\nPack Description: "${packDescription}"\nUse this description to guide the theme and style of questions.`
         : '';
 
-    const prompt = `Generate ${count} unique questions for a couples' intimacy question pack called "${packName}".${descriptionContext}
+    const existingQuestionsContext = existingQuestions && existingQuestions.length > 0
+        ? `\n\nEXISTING QUESTIONS IN THIS PACK (DO NOT DUPLICATE OR CREATE SIMILAR VARIATIONS):
+${existingQuestions.map((q, i) => `${i + 1}. ${q}`).join('\n')}
+
+CRITICAL: Generate completely NEW and DIFFERENT questions. Do not repeat any of the above questions or create minor variations of them. Each new question must offer a genuinely distinct activity or experience.`
+        : '';
+
+    const prompt = `Generate ${count} unique questions for a couples' intimacy question pack called "${packName}".${descriptionContext}${existingQuestionsContext}
 
 ${INTENSITY_GUIDE_SHORT}
 
diff --git a/apps/admin/src/pages/content/QuestionsPage.tsx b/apps/admin/src/pages/content/QuestionsPage.tsx
index cca2258..eb1b0de 100644
--- a/apps/admin/src/pages/content/QuestionsPage.tsx
+++ b/apps/admin/src/pages/content/QuestionsPage.tsx
@@ -440,7 +440,7 @@ export function QuestionsPage() {
                 open={aiDialogOpen}
                 onOpenChange={setAiDialogOpen}
                 type="questions"
-                context={{ packName: pack?.name, packDescription: pack?.description, isExplicit: pack?.is_explicit }}
+                context={{ packName: pack?.name, packDescription: pack?.description, isExplicit: pack?.is_explicit, existingQuestions: questions.map(q => q.text) }}
                 onGenerated={handleAiGenerated}
             />