diff --git a/src/database/db.sqlite3 b/src/database/db.sqlite3
index b54da94..04fcd5a 100644
Binary files a/src/database/db.sqlite3 and b/src/database/db.sqlite3 differ
diff --git a/src/web/ai-helper.ts b/src/web/ai-helper.ts
new file mode 100644
index 0000000..c767602
--- /dev/null
+++ b/src/web/ai-helper.ts
@@ -0,0 +1,278 @@
+/**
+ * AI Helper for personality configuration
+ * Provides an intelligent assistant to help users create and refine personality prompts
+ */
+
+import { Hono } from "hono";
+import OpenAI from "openai";
+import { config } from "../core/config";
+import { createLogger } from "../core/logger";
+import { requireAuth } from "./session";
+import { JOEL_TOOLS, GIF_SEARCH_TOOL } from "../services/ai/tools";
+import { STYLE_MODIFIERS } from "../features/joel/personalities";
+
+const logger = createLogger("Web:AIHelper");
+
+/**
+ * System prompt for the AI helper - it knows about personality configuration
+ */
+const AI_HELPER_SYSTEM_PROMPT = `You are a helpful assistant for configuring AI personality prompts for "Joel", a Discord bot.
+Your job is to help users create effective system prompts that define Joel's personality and behavior.
+
+You have expert knowledge about:
+1. How system prompts work and best practices for writing them
+2. The available template variables users can use in their prompts
+3. The tools that Joel can use during conversations
+4. Style modifiers that affect Joel's behavior
+
+AVAILABLE TEMPLATE VARIABLES:
+Users can include these in their prompts - they will be replaced with actual values at runtime:
+- {author} - Display name of the user talking to Joel
+- {username} - Discord username
+- {userId} - Discord user ID
+- {channelName} - Current channel name
+- {channelId} - Current channel ID
+- {guildName} - Server name
+- {guildId} - Server ID
+- {messageContent} - The user's message
+- {memories} - Stored memories about the user (collected from past conversations)
+- {style} - Detected message style (story, snarky, insult, explicit, helpful)
+- {styleModifier} - Style-specific instructions based on the detected style
+- {timestamp} - Current date/time in ISO format
+
+AVAILABLE TOOLS (Joel can use these during conversations):
+${JOEL_TOOLS.map(t => `- ${t.function.name}: ${t.function.description}`).join('\n')}
+- ${GIF_SEARCH_TOOL.function.name}: ${GIF_SEARCH_TOOL.function.description} (only when GIF search is enabled)
+
+STYLE MODIFIERS (applied based on detected message intent):
+${Object.entries(STYLE_MODIFIERS).map(([style, modifier]) => `- ${style}: ${modifier.split('\n')[0]}`).join('\n')}
+
+TIPS FOR GOOD PROMPTS:
+1. Be specific about the personality traits you want
+2. Use {author} to personalize responses with the user's name
+3. Include {memories} if you want Joel to use remembered facts about users
+4. Define clear boundaries and behaviors
+5. Include example responses if helpful
+6. Consider how the style modifiers will interact with your base prompt
+
+When helping users, you should:
+- Explain concepts clearly
+- Provide examples when helpful
+- Suggest improvements to their prompts
+- Answer questions about variables and tools
+- Help them understand how Joel will interpret their prompts
+
+Keep responses helpful but concise. Format code/prompts in code blocks when showing examples.`;
+
+export function createAiHelperRoutes() {
+  const app = new Hono();
+
+  // Require authentication for all AI helper routes
+  app.use("/*", requireAuth);
+
+  // Get context information for the AI helper UI
+  app.get("/context", async (c) => {
+    return c.json({
+      variables: [
+        { name: "{author}", description: "Display name of the user" },
+        { name: "{username}", description: "Discord username" },
+        { name: "{userId}", description: "Discord user ID" },
+        { name: "{channelName}", description: "Current channel name" },
+        { name: "{channelId}", description: "Current channel ID" },
+        { name: "{guildName}", description: "Server name" },
+        { name: "{guildId}", description: "Server ID" },
+        { name: "{messageContent}", description: "The user's message" },
+        { name: "{memories}", description: "Stored memories about the user" },
+        { name: "{style}", description: "Detected message style" },
+        { name: "{styleModifier}", description: "Style-specific instructions" },
+        { name: "{timestamp}", description: "Current date/time" },
+      ],
+      tools: [
+        ...JOEL_TOOLS.map(t => ({
+          name: t.function.name,
+          description: t.function.description,
+          parameters: t.function.parameters,
+        })),
+        {
+          name: GIF_SEARCH_TOOL.function.name,
+          description: GIF_SEARCH_TOOL.function.description + " (requires GIF search to be enabled)",
+          parameters: GIF_SEARCH_TOOL.function.parameters,
+        },
+      ],
+      styles: Object.entries(STYLE_MODIFIERS).map(([name, modifier]) => ({
+        name,
+        description: modifier,
+      })),
+    });
+  });
+
+  // Chat endpoint for the AI helper
+  app.post("/chat", async (c) => {
+    try {
+      const body = await c.req.json<{ 
+        message: string; 
+        history?: { role: "user" | "assistant"; content: string }[];
+        currentPrompt?: string;
+      }>();
+
+      if (!body.message) {
+        return c.json({ error: "Message is required" }, 400);
+      }
+
+      const client = new OpenAI({
+        baseURL: "https://openrouter.ai/api/v1",
+        apiKey: config.ai.openRouterApiKey,
+        defaultHeaders: {
+          "HTTP-Referer": "https://github.com/crunk-bun",
+          "X-Title": "Joel Bot - AI Helper",
+        },
+      });
+
+      // Build messages array with history
+      const messages: { role: "system" | "user" | "assistant"; content: string }[] = [
+        { role: "system", content: AI_HELPER_SYSTEM_PROMPT },
+      ];
+
+      // Add conversation history
+      if (body.history && body.history.length > 0) {
+        messages.push(...body.history);
+      }
+
+      // If there's a current prompt being edited, include it as context
+      let userMessage = body.message;
+      if (body.currentPrompt) {
+        userMessage = `[Current personality prompt being edited:\n\`\`\`\n${body.currentPrompt}\n\`\`\`]\n\n${body.message}`;
+      }
+
+      messages.push({ role: "user", content: userMessage });
+
+      const completion = await client.chat.completions.create({
+        model: config.ai.classificationModel, // Use the lighter model for helper
+        messages,
+        max_tokens: 1000,
+        temperature: 0.7,
+      });
+
+      const response = completion.choices[0]?.message?.content ?? "I couldn't generate a response. Please try again.";
+
+      return c.json({ response });
+    } catch (error) {
+      logger.error("AI helper chat error", error);
+      return c.json({ error: "Failed to generate response" }, 500);
+    }
+  });
+
+  // Generate a personality prompt based on description
+  app.post("/generate", async (c) => {
+    try {
+      const body = await c.req.json<{ 
+        description: string;
+        includeMemories?: boolean;
+        includeStyles?: boolean;
+      }>();
+
+      if (!body.description) {
+        return c.json({ error: "Description is required" }, 400);
+      }
+
+      const client = new OpenAI({
+        baseURL: "https://openrouter.ai/api/v1",
+        apiKey: config.ai.openRouterApiKey,
+        defaultHeaders: {
+          "HTTP-Referer": "https://github.com/crunk-bun",
+          "X-Title": "Joel Bot - AI Helper",
+        },
+      });
+
+      const generatePrompt = `Based on the following description, generate a complete system prompt for the Joel Discord bot personality.
+
+User's description: "${body.description}"
+
+Requirements:
+- The prompt should define a clear personality
+- Include {author} to personalize with the user's name
+${body.includeMemories ? '- Include {memories} to use stored facts about users' : ''}
+${body.includeStyles ? '- Include {style} and {styleModifier} for style-aware responses' : ''}
+- Be specific and actionable
+- Keep it focused but comprehensive
+
+Generate ONLY the system prompt text, no explanations or markdown code blocks.`;
+
+      const completion = await client.chat.completions.create({
+        model: config.ai.classificationModel,
+        messages: [
+          { role: "system", content: "You are an expert at writing AI system prompts. Generate clear, effective prompts based on user descriptions." },
+          { role: "user", content: generatePrompt },
+        ],
+        max_tokens: 800,
+        temperature: 0.8,
+      });
+
+      const generatedPrompt = completion.choices[0]?.message?.content ?? "";
+
+      return c.json({ prompt: generatedPrompt });
+    } catch (error) {
+      logger.error("AI helper generate error", error);
+      return c.json({ error: "Failed to generate prompt" }, 500);
+    }
+  });
+
+  // Improve an existing prompt
+  app.post("/improve", async (c) => {
+    try {
+      const body = await c.req.json<{ 
+        prompt: string;
+        feedback?: string;
+      }>();
+
+      if (!body.prompt) {
+        return c.json({ error: "Prompt is required" }, 400);
+      }
+
+      const client = new OpenAI({
+        baseURL: "https://openrouter.ai/api/v1",
+        apiKey: config.ai.openRouterApiKey,
+        defaultHeaders: {
+          "HTTP-Referer": "https://github.com/crunk-bun",
+          "X-Title": "Joel Bot - AI Helper",
+        },
+      });
+
+      const improvePrompt = `Review and improve the following system prompt for a Discord bot personality:
+
+Current prompt:
+"""
+${body.prompt}
+"""
+
+${body.feedback ? `User's feedback: "${body.feedback}"` : 'Improve clarity, effectiveness, and make sure it uses available features well.'}
+
+Available template variables: {author}, {username}, {userId}, {channelName}, {channelId}, {guildName}, {guildId}, {messageContent}, {memories}, {style}, {styleModifier}, {timestamp}
+
+Provide:
+1. The improved prompt (in a code block)
+2. Brief explanation of changes made
+
+Keep the same general intent but make it more effective.`;
+
+      const completion = await client.chat.completions.create({
+        model: config.ai.classificationModel,
+        messages: [
+          { role: "system", content: "You are an expert at improving AI system prompts. Provide clear improvements while maintaining the original intent." },
+          { role: "user", content: improvePrompt },
+        ],
+        max_tokens: 1200,
+        temperature: 0.7,
+      });
+
+      const response = completion.choices[0]?.message?.content ?? "";
+
+      return c.json({ response });
+    } catch (error) {
+      logger.error("AI helper improve error", error);
+      return c.json({ error: "Failed to improve prompt" }, 500);
+    }
+  });
+
+  return app;
+}
diff --git a/src/web/index.ts b/src/web/index.ts
index 019e8b7..f830c50 100644
--- a/src/web/index.ts
+++ b/src/web/index.ts
@@ -10,7 +10,8 @@ import type { BotClient } from "../core/client";
 import * as oauth from "./oauth";
 import * as session from "./session";
 import { createApiRoutes } from "./api";
-import { loginPage, dashboardPage, guildDetailPage } from "./templates";
+import { createAiHelperRoutes } from "./ai-helper";
+import { loginPage, dashboardPage, guildDetailPage, aiHelperPage } from "./templates";
 import { db } from "../database";
 import { personalities, botOptions } from "../database/schema";
 import { eq } from "drizzle-orm";
@@ -141,6 +142,29 @@ export function createWebServer(client: BotClient) {
   // Mount API routes
   app.route("/api", createApiRoutes(client));
 
+  // Mount AI helper routes
+  app.route("/ai-helper", createAiHelperRoutes());
+
+  // AI Helper page
+  app.get("/ai-helper", async (c) => {
+    const sessionId = session.getSessionCookie(c);
+    const sess = sessionId ? await session.getSession(sessionId) : null;
+
+    if (!sess) {
+      return c.redirect("/");
+    }
+
+    // Check for optional guild context
+    const guildId = c.req.query("guild");
+    let guildName: string | undefined;
+    
+    if (guildId && client.guilds.cache.has(guildId)) {
+      guildName = client.guilds.cache.get(guildId)?.name;
+    }
+
+    return c.html(aiHelperPage(guildId, guildName));
+  });
+
   // Dashboard - requires auth
   app.get("/", async (c) => {
     const sessionId = session.getSessionCookie(c);
diff --git a/src/web/templates/ai-helper.ts b/src/web/templates/ai-helper.ts
new file mode 100644
index 0000000..93e71c0
--- /dev/null
+++ b/src/web/templates/ai-helper.ts
@@ -0,0 +1,656 @@
+/**
+ * AI Helper page template
+ * Provides an interactive chat interface for personality configuration assistance
+ */
+
+import { page } from "./base";
+
+const aiHelperStyles = `
+  .ai-helper-container {
+    display: grid;
+    grid-template-columns: 1fr 350px;
+    gap: 24px;
+    margin-top: 24px;
+  }
+  
+  @media (max-width: 900px) {
+    .ai-helper-container {
+      grid-template-columns: 1fr;
+    }
+  }
+  
+  /* Chat section */
+  .chat-section {
+    display: flex;
+    flex-direction: column;
+    height: calc(100vh - 200px);
+    min-height: 500px;
+  }
+  
+  .chat-messages {
+    flex: 1;
+    overflow-y: auto;
+    padding: 16px;
+    background: #1a1a1a;
+    border: 1px solid #2a2a2a;
+    border-radius: 12px 12px 0 0;
+    display: flex;
+    flex-direction: column;
+    gap: 16px;
+  }
+  
+  .chat-message {
+    max-width: 85%;
+    padding: 12px 16px;
+    border-radius: 12px;
+    line-height: 1.5;
+  }
+  
+  .chat-message.user {
+    align-self: flex-end;
+    background: #5865F2;
+    color: white;
+  }
+  
+  .chat-message.assistant {
+    align-self: flex-start;
+    background: #252525;
+    color: #e0e0e0;
+  }
+  
+  .chat-message pre {
+    background: #1a1a1a;
+    padding: 12px;
+    border-radius: 6px;
+    overflow-x: auto;
+    margin: 8px 0;
+    font-size: 12px;
+  }
+  
+  .chat-message code {
+    background: #1a1a1a;
+    padding: 2px 6px;
+    border-radius: 4px;
+    font-size: 13px;
+  }
+  
+  .chat-input-container {
+    display: flex;
+    gap: 8px;
+    padding: 16px;
+    background: #1a1a1a;
+    border: 1px solid #2a2a2a;
+    border-top: none;
+    border-radius: 0 0 12px 12px;
+  }
+  
+  .chat-input {
+    flex: 1;
+    padding: 12px 16px;
+    border: 1px solid #3a3a3a;
+    border-radius: 8px;
+    background: #2a2a2a;
+    color: #e0e0e0;
+    font-size: 14px;
+    resize: none;
+    min-height: 44px;
+    max-height: 120px;
+  }
+  
+  .chat-input:focus {
+    outline: none;
+    border-color: #5865F2;
+  }
+  
+  .chat-send-btn {
+    padding: 12px 24px;
+    background: #5865F2;
+    color: white;
+    border: none;
+    border-radius: 8px;
+    cursor: pointer;
+    font-weight: 500;
+    transition: background 0.2s;
+  }
+  
+  .chat-send-btn:hover {
+    background: #4752C4;
+  }
+  
+  .chat-send-btn:disabled {
+    background: #4a4a4a;
+    cursor: not-allowed;
+  }
+  
+  /* Reference panel */
+  .reference-panel {
+    background: #1a1a1a;
+    border: 1px solid #2a2a2a;
+    border-radius: 12px;
+    padding: 20px;
+    height: fit-content;
+    max-height: calc(100vh - 200px);
+    overflow-y: auto;
+    position: sticky;
+    top: 20px;
+  }
+  
+  .reference-section {
+    margin-bottom: 24px;
+  }
+  
+  .reference-section:last-child {
+    margin-bottom: 0;
+  }
+  
+  .reference-section h4 {
+    margin: 0 0 12px 0;
+    color: #5865F2;
+    font-size: 14px;
+    text-transform: uppercase;
+    letter-spacing: 0.5px;
+  }
+  
+  .reference-item {
+    padding: 8px 10px;
+    background: #252525;
+    border-radius: 6px;
+    margin-bottom: 6px;
+    font-size: 13px;
+  }
+  
+  .reference-item code {
+    color: #4ade80;
+    background: #1a2a1a;
+    padding: 2px 6px;
+    border-radius: 4px;
+    font-size: 12px;
+  }
+  
+  .reference-item .desc {
+    color: #888;
+    font-size: 11px;
+    margin-top: 4px;
+  }
+  
+  .tool-item {
+    padding: 8px 10px;
+    background: #252535;
+    border-radius: 6px;
+    margin-bottom: 6px;
+  }
+  
+  .tool-item .name {
+    color: #a78bfa;
+    font-weight: 500;
+    font-size: 12px;
+  }
+  
+  .tool-item .desc {
+    color: #888;
+    font-size: 11px;
+    margin-top: 4px;
+  }
+  
+  /* Quick actions */
+  .quick-actions {
+    display: flex;
+    flex-wrap: wrap;
+    gap: 8px;
+    margin-bottom: 16px;
+  }
+  
+  .quick-action {
+    padding: 8px 14px;
+    background: #252525;
+    border: 1px solid #3a3a3a;
+    border-radius: 20px;
+    color: #b0b0b0;
+    font-size: 13px;
+    cursor: pointer;
+    transition: all 0.2s;
+  }
+  
+  .quick-action:hover {
+    background: #353535;
+    color: #fff;
+    border-color: #5865F2;
+  }
+  
+  /* Prompt editor panel */
+  .prompt-editor-panel {
+    margin-top: 16px;
+    padding: 16px;
+    background: #1a2a1a;
+    border-radius: 8px;
+    border: 1px solid #2a3a2a;
+  }
+  
+  .prompt-editor-panel h4 {
+    margin: 0 0 12px 0;
+    color: #4ade80;
+    font-size: 14px;
+  }
+  
+  .prompt-editor-panel textarea {
+    width: 100%;
+    min-height: 150px;
+    padding: 12px;
+    background: #252535;
+    border: 1px solid #3a3a3a;
+    border-radius: 6px;
+    color: #e0e0e0;
+    font-family: monospace;
+    font-size: 12px;
+    resize: vertical;
+  }
+  
+  .prompt-editor-panel textarea:focus {
+    outline: none;
+    border-color: #4ade80;
+  }
+  
+  .prompt-actions {
+    display: flex;
+    gap: 8px;
+    margin-top: 12px;
+  }
+  
+  .typing-indicator {
+    display: flex;
+    gap: 4px;
+    padding: 12px 16px;
+    align-self: flex-start;
+    background: #252525;
+    border-radius: 12px;
+  }
+  
+  .typing-indicator span {
+    width: 8px;
+    height: 8px;
+    background: #5865F2;
+    border-radius: 50%;
+    animation: typing 1.4s infinite;
+  }
+  
+  .typing-indicator span:nth-child(2) { animation-delay: 0.2s; }
+  .typing-indicator span:nth-child(3) { animation-delay: 0.4s; }
+  
+  @keyframes typing {
+    0%, 60%, 100% { transform: translateY(0); opacity: 0.6; }
+    30% { transform: translateY(-4px); opacity: 1; }
+  }
+  
+  .welcome-message {
+    text-align: center;
+    padding: 40px 20px;
+    color: #888;
+  }
+  
+  .welcome-message h3 {
+    color: #fff;
+    margin-bottom: 16px;
+  }
+  
+  .welcome-message p {
+    margin: 8px 0;
+  }
+`;
+
+const aiHelperScripts = `
+  let chatHistory = [];
+  let isProcessing = false;
+  
+  // Auto-resize textarea
+  const chatInput = document.getElementById('chat-input');
+  chatInput.addEventListener('input', function() {
+    this.style.height = 'auto';
+    this.style.height = Math.min(this.scrollHeight, 120) + 'px';
+  });
+  
+  // Send on Enter (Shift+Enter for newline)
+  chatInput.addEventListener('keydown', function(e) {
+    if (e.key === 'Enter' && !e.shiftKey) {
+      e.preventDefault();
+      sendMessage();
+    }
+  });
+  
+  async function sendMessage(customMessage) {
+    if (isProcessing) return;
+    
+    const input = document.getElementById('chat-input');
+    const message = customMessage || input.value.trim();
+    if (!message) return;
+    
+    isProcessing = true;
+    input.value = '';
+    input.style.height = 'auto';
+    
+    const sendBtn = document.getElementById('send-btn');
+    sendBtn.disabled = true;
+    
+    // Add user message
+    addMessage('user', message);
+    chatHistory.push({ role: 'user', content: message });
+    
+    // Show typing indicator
+    const messagesContainer = document.getElementById('chat-messages');
+    const typingDiv = document.createElement('div');
+    typingDiv.className = 'typing-indicator';
+    typingDiv.id = 'typing-indicator';
+    typingDiv.innerHTML = '<span></span><span></span><span></span>';
+    messagesContainer.appendChild(typingDiv);
+    messagesContainer.scrollTop = messagesContainer.scrollHeight;
+    
+    try {
+      // Get current prompt if any
+      const promptEditor = document.getElementById('current-prompt');
+      const currentPrompt = promptEditor ? promptEditor.value.trim() : '';
+      
+      const response = await fetch('/ai-helper/chat', {
+        method: 'POST',
+        headers: { 'Content-Type': 'application/json' },
+        body: JSON.stringify({
+          message,
+          history: chatHistory.slice(0, -1), // Don't include the message we just added
+          currentPrompt: currentPrompt || undefined
+        })
+      });
+      
+      const data = await response.json();
+      
+      // Remove typing indicator
+      document.getElementById('typing-indicator')?.remove();
+      
+      if (data.error) {
+        addMessage('assistant', 'Sorry, I encountered an error. Please try again.');
+      } else {
+        addMessage('assistant', data.response);
+        chatHistory.push({ role: 'assistant', content: data.response });
+      }
+    } catch (error) {
+      document.getElementById('typing-indicator')?.remove();
+      addMessage('assistant', 'Sorry, I couldn\\'t connect to the server. Please try again.');
+    }
+    
+    isProcessing = false;
+    sendBtn.disabled = false;
+    input.focus();
+  }
+  
+  function addMessage(role, content) {
+    const messagesContainer = document.getElementById('chat-messages');
+    const welcomeMessage = document.querySelector('.welcome-message');
+    if (welcomeMessage) welcomeMessage.remove();
+    
+    const messageDiv = document.createElement('div');
+    messageDiv.className = 'chat-message ' + role;
+    
+    // Basic markdown rendering
+    let html = content
+      .replace(/\`\`\`([\\s\\S]*?)\`\`\`/g, '<pre>$1</pre>')
+      .replace(/\`([^\`]+)\`/g, '<code>$1</code>')
+      .replace(/\\n/g, '<br>');
+    
+    messageDiv.innerHTML = html;
+    messagesContainer.appendChild(messageDiv);
+    messagesContainer.scrollTop = messagesContainer.scrollHeight;
+  }
+  
+  function quickAction(action) {
+    const actions = {
+      'explain-variables': 'Explain all the template variables I can use in my prompts and when to use each one.',
+      'explain-tools': 'What tools does Joel have access to? How do they work?',
+      'explain-styles': 'What are the different message styles and how do they affect responses?',
+      'example-prompt': 'Show me an example of a well-written personality prompt with explanations.',
+      'improve-prompt': 'Can you review my current prompt and suggest improvements?',
+      'create-sarcastic': 'Help me create a sarcastic but funny personality.',
+      'create-helpful': 'Help me create a helpful assistant personality.',
+      'create-character': 'Help me create a personality based on a fictional character.'
+    };
+    
+    if (actions[action]) {
+      sendMessage(actions[action]);
+    }
+  }
+  
+  async function generatePrompt() {
+    const description = document.getElementById('generate-description').value.trim();
+    if (!description) return;
+    
+    const btn = event.target;
+    btn.disabled = true;
+    btn.textContent = 'Generating...';
+    
+    try {
+      const includeMemories = document.getElementById('include-memories').checked;
+      const includeStyles = document.getElementById('include-styles').checked;
+      
+      const response = await fetch('/ai-helper/generate', {
+        method: 'POST',
+        headers: { 'Content-Type': 'application/json' },
+        body: JSON.stringify({ description, includeMemories, includeStyles })
+      });
+      
+      const data = await response.json();
+      
+      if (data.prompt) {
+        document.getElementById('current-prompt').value = data.prompt;
+        addMessage('assistant', 'I\\'ve generated a prompt based on your description! You can see it in the "Current Prompt" editor below. Feel free to ask me to modify it or explain any part.');
+        chatHistory.push({ role: 'assistant', content: 'Generated a new prompt based on user description.' });
+      }
+    } catch (error) {
+      addMessage('assistant', 'Sorry, I couldn\\'t generate the prompt. Please try again.');
+    }
+    
+    btn.disabled = false;
+    btn.textContent = 'Generate';
+  }
+  
+  async function improvePrompt() {
+    const prompt = document.getElementById('current-prompt').value.trim();
+    if (!prompt) {
+      addMessage('assistant', 'Please add a prompt to the editor first, then I can help improve it.');
+      return;
+    }
+    
+    sendMessage('Please review and improve my current prompt. Make it more effective while keeping the same general intent.');
+  }
+  
+  function copyPrompt() {
+    const prompt = document.getElementById('current-prompt').value;
+    navigator.clipboard.writeText(prompt);
+    
+    const btn = event.target;
+    const originalText = btn.textContent;
+    btn.textContent = 'Copied!';
+    setTimeout(() => btn.textContent = originalText, 2000);
+  }
+`;
+
+export function aiHelperPage(guildId?: string, guildName?: string): string {
+  return page({
+    title: "AI Personality Helper - Joel Bot",
+    styles: aiHelperStyles,
+    content: `
+      <div class="container">
+        <div class="header">
+          <div>
+            <h1>🧠 AI Personality Helper</h1>
+            <p style="color: #888; margin: 4px 0 0 0;">Get help creating and refining Joel's personality prompts</p>
+          </div>
+          <div class="user-info">
+            ${guildId ? `<span>Configuring: ${escapeHtml(guildName || guildId)}</span>` : ''}
+            <a href="/dashboard" class="btn btn-secondary btn-sm">← Back to Dashboard</a>
+          </div>
+        </div>
+        
+        <div class="quick-actions">
+          <button class="quick-action" onclick="quickAction('explain-variables')">📝 Variables</button>
+          <button class="quick-action" onclick="quickAction('explain-tools')">🔧 Tools</button>
+          <button class="quick-action" onclick="quickAction('explain-styles')">🎭 Styles</button>
+          <button class="quick-action" onclick="quickAction('example-prompt')">💡 Example</button>
+          <button class="quick-action" onclick="quickAction('create-sarcastic')">😏 Sarcastic</button>
+          <button class="quick-action" onclick="quickAction('create-helpful')">🤝 Helpful</button>
+          <button class="quick-action" onclick="quickAction('create-character')">🎬 Character</button>
+        </div>
+        
+        <div class="ai-helper-container">
+          <div>
+            <!-- Chat section -->
+            <div class="chat-section">
+              <div class="chat-messages" id="chat-messages">
+                <div class="welcome-message">
+                  <h3>👋 Hi! I'm here to help you create personality prompts.</h3>
+                  <p>Ask me anything about:</p>
+                  <p>• Template variables and how to use them</p>
+                  <p>• Available tools Joel can use</p>
+                  <p>• Style modifiers and their effects</p>
+                  <p>• Best practices for prompt writing</p>
+                  <p style="margin-top: 16px; color: #5865F2;">Try one of the quick action buttons above, or just ask a question!</p>
+                </div>
+              </div>
+              <div class="chat-input-container">
+                <textarea 
+                  id="chat-input" 
+                  class="chat-input" 
+                  placeholder="Ask about variables, tools, or get help with your prompt..."
+                  rows="1"
+                ></textarea>
+                <button id="send-btn" class="chat-send-btn" onclick="sendMessage()">Send</button>
+              </div>
+            </div>
+            
+            <!-- Prompt editor -->
+            <div class="prompt-editor-panel">
+              <h4>📋 Current Prompt (Working Area)</h4>
+              <textarea id="current-prompt" placeholder="Paste or write your prompt here. The AI helper can see this and help you improve it."></textarea>
+              <div class="prompt-actions">
+                <button class="btn btn-sm" onclick="improvePrompt()">✨ Improve This</button>
+                <button class="btn btn-sm btn-secondary" onclick="copyPrompt()">📋 Copy</button>
+              </div>
+            </div>
+            
+            <!-- Quick generate -->
+            <div class="card" style="margin-top: 16px;">
+              <h3>⚡ Quick Generate</h3>
+              <p style="color: #888; margin-bottom: 12px;">Describe the personality you want and I'll generate a prompt for you.</p>
+              <div class="form-group">
+                <textarea id="generate-description" placeholder="e.g., A grumpy wizard who speaks in riddles and gets annoyed easily..." style="min-height: 80px;"></textarea>
+              </div>
+              <div style="display: flex; gap: 16px; align-items: center; flex-wrap: wrap;">
+                <label style="display: flex; align-items: center; gap: 8px; cursor: pointer; color: #888;">
+                  <input type="checkbox" id="include-memories" checked style="width: 16px; height: 16px;">
+                  Include memories
+                </label>
+                <label style="display: flex; align-items: center; gap: 8px; cursor: pointer; color: #888;">
+                  <input type="checkbox" id="include-styles" checked style="width: 16px; height: 16px;">
+                  Include style handling
+                </label>
+                <button class="btn" onclick="generatePrompt()">Generate</button>
+              </div>
+            </div>
+          </div>
+          
+          <!-- Reference panel -->
+          <div class="reference-panel">
+            <div class="reference-section">
+              <h4>📝 Template Variables</h4>
+              <div class="reference-item">
+                <code>{author}</code>
+                <div class="desc">User's display name</div>
+              </div>
+              <div class="reference-item">
+                <code>{username}</code>
+                <div class="desc">Discord username</div>
+              </div>
+              <div class="reference-item">
+                <code>{memories}</code>
+                <div class="desc">Stored memories about user</div>
+              </div>
+              <div class="reference-item">
+                <code>{style}</code>
+                <div class="desc">Detected message style</div>
+              </div>
+              <div class="reference-item">
+                <code>{styleModifier}</code>
+                <div class="desc">Style instructions</div>
+              </div>
+              <div class="reference-item">
+                <code>{channelName}</code>
+                <div class="desc">Current channel</div>
+              </div>
+              <div class="reference-item">
+                <code>{guildName}</code>
+                <div class="desc">Server name</div>
+              </div>
+              <div class="reference-item">
+                <code>{timestamp}</code>
+                <div class="desc">Current date/time</div>
+              </div>
+            </div>
+            
+            <div class="reference-section">
+              <h4>🔧 Available Tools</h4>
+              <div class="tool-item">
+                <div class="name">lookup_user_memories</div>
+                <div class="desc">Look up what's remembered about a user</div>
+              </div>
+              <div class="tool-item">
+                <div class="name">save_memory</div>
+                <div class="desc">Save info about a user for later</div>
+              </div>
+              <div class="tool-item">
+                <div class="name">search_memories</div>
+                <div class="desc">Search all memories by keyword</div>
+              </div>
+              <div class="tool-item">
+                <div class="name">get_memory_stats</div>
+                <div class="desc">Get memory statistics</div>
+              </div>
+              <div class="tool-item">
+                <div class="name">search_gif</div>
+                <div class="desc">Search for GIFs (when enabled)</div>
+              </div>
+            </div>
+            
+            <div class="reference-section">
+              <h4>🎭 Message Styles</h4>
+              <div class="reference-item">
+                <code>story</code>
+                <div class="desc">Creative storytelling mode</div>
+              </div>
+              <div class="reference-item">
+                <code>snarky</code>
+                <div class="desc">Sarcastic and witty</div>
+              </div>
+              <div class="reference-item">
+                <code>insult</code>
+                <div class="desc">Brutal roast mode</div>
+              </div>
+              <div class="reference-item">
+                <code>explicit</code>
+                <div class="desc">Unfiltered adult content</div>
+              </div>
+              <div class="reference-item">
+                <code>helpful</code>
+                <div class="desc">Actually useful responses</div>
+              </div>
+            </div>
+          </div>
+        </div>
+      </div>
+    `,
+    scripts: aiHelperScripts,
+  });
+}
+
+function escapeHtml(text: string): string {
+  return text
+    .replace(/&/g, '&amp;')
+    .replace(/</g, '&lt;')
+    .replace(/>/g, '&gt;')
+    .replace(/"/g, '&quot;')
+    .replace(/'/g, '&#039;');
+}
diff --git a/src/web/templates/dashboard.ts b/src/web/templates/dashboard.ts
index 3b250de..aaa3298 100644
--- a/src/web/templates/dashboard.ts
+++ b/src/web/templates/dashboard.ts
@@ -38,6 +38,7 @@ export function dashboardPage(user: User, guilds: Guild[]): string {
           <h1>🤖 Joel Bot Dashboard</h1>
           <div class="user-info">
             <span>${user.global_name || user.username}</span>
+            <a href="/ai-helper" class="btn btn-sm" style="background: #9333ea;">🧠 AI Helper</a>
             <button class="btn btn-secondary btn-sm" hx-post="/auth/logout" hx-redirect="/">Logout</button>
           </div>
         </div>
@@ -86,11 +87,15 @@ export function guildDetailPage(guildId: string, guildName: string, options: Bot
       <!-- System Prompts Tab -->
       <div id="tab-prompts" class="tab-content active">
         <div class="card">
-          <h3>Custom System Prompts</h3>
-          <p style="color: #888; margin-bottom: 20px;">
-            Create custom personalities for Joel by defining different system prompts.
-            The active personality will be used when Joel responds in this server.
-          </p>
+          <div style="display: flex; justify-content: space-between; align-items: center; margin-bottom: 16px;">
+            <div>
+              <h3 style="margin: 0;">Custom System Prompts</h3>
+              <p style="color: #888; margin: 8px 0 0 0;">
+                Create custom personalities for Joel by defining different system prompts.
+              </p>
+            </div>
+            <a href="/ai-helper?guild=${guildId}" class="btn btn-sm" style="background: #9333ea;">🧠 AI Helper</a>
+          </div>
           
           <div id="personalities-list">
             ${personalities.length === 0 
diff --git a/src/web/templates/index.ts b/src/web/templates/index.ts
index f087392..fb4f87e 100644
--- a/src/web/templates/index.ts
+++ b/src/web/templates/index.ts
@@ -11,3 +11,4 @@ export {
   viewPromptModal, 
   editPromptModal 
 } from "./dashboard";
+export { aiHelperPage } from "./ai-helper";