diff --git a/src-tauri/src/achievements.rs b/src-tauri/src/achievements.rs
index 5497597..55cd09d 100644
--- a/src-tauri/src/achievements.rs
+++ b/src-tauri/src/achievements.rs
@@ -55,6 +55,28 @@ pub enum AchievementId {
     SpeedCoder,      // 10 code blocks in 10 minutes
     ClaudeConnoisseur, // Used all Claude models
     MarathonCoder,   // 10k tokens in one session
+
+    // Relationship & Greetings
+    GoodMorning,     // Say "good morning"
+    GoodNight,       // Say "good night" or "goodnight"
+    ThankYou,        // Say "thank you" or "thanks"
+    LoveYou,         // Say "love you" or "ily"
+
+    // Personality & Fun
+    EmojiUser,       // Use an emoji in a message
+    QuestionMaster,  // Use "?" in 20 messages
+    CapsLock,        // Send a message in ALL CAPS
+    PleaseAndThankYou, // Use "please" in messages
+
+    // Git & Development
+    GitGuru,         // Use git commands 10 times
+    TestWriter,      // Create test files
+    Debugger,        // Fix bugs (messages with "fix", "bug", "error")
+
+    // Tool Mastery
+    BashMaster,      // Use Bash tool 50 times
+    FileExplorer,    // Use Read tool 100 times
+    SearchExpert,    // Use Grep tool 50 times
 }
 
 #[derive(Debug, Clone, Serialize, Deserialize)]
@@ -361,9 +383,164 @@ pub fn get_achievement_info(id: &AchievementId) -> Achievement {
             icon: "🏃‍♂️".to_string(),
             unlocked_at: None,
         },
+
+        // Relationship & Greetings
+        AchievementId::GoodMorning => Achievement {
+            id: id.clone(),
+            name: "Good Morning!".to_string(),
+            description: "Greeted Hikari with a good morning".to_string(),
+            icon: "🌅".to_string(),
+            unlocked_at: None,
+        },
+        AchievementId::GoodNight => Achievement {
+            id: id.clone(),
+            name: "Good Night".to_string(),
+            description: "Said good night to Hikari".to_string(),
+            icon: "🌙".to_string(),
+            unlocked_at: None,
+        },
+        AchievementId::ThankYou => Achievement {
+            id: id.clone(),
+            name: "Grateful Heart".to_string(),
+            description: "Thanked Hikari for her help".to_string(),
+            icon: "💝".to_string(),
+            unlocked_at: None,
+        },
+        AchievementId::LoveYou => Achievement {
+            id: id.clone(),
+            name: "Love Connection".to_string(),
+            description: "Expressed love to Hikari".to_string(),
+            icon: "💕".to_string(),
+            unlocked_at: None,
+        },
+
+        // Personality & Fun
+        AchievementId::EmojiUser => Achievement {
+            id: id.clone(),
+            name: "Emoji Enthusiast".to_string(),
+            description: "Used an emoji in your message".to_string(),
+            icon: "😊".to_string(),
+            unlocked_at: None,
+        },
+        AchievementId::QuestionMaster => Achievement {
+            id: id.clone(),
+            name: "Question Master".to_string(),
+            description: "Asked 20 questions".to_string(),
+            icon: "❓".to_string(),
+            unlocked_at: None,
+        },
+        AchievementId::CapsLock => Achievement {
+            id: id.clone(),
+            name: "CAPS LOCK ENGAGED".to_string(),
+            description: "SENT A MESSAGE IN ALL CAPS".to_string(),
+            icon: "📢".to_string(),
+            unlocked_at: None,
+        },
+        AchievementId::PleaseAndThankYou => Achievement {
+            id: id.clone(),
+            name: "Polite Programmer".to_string(),
+            description: "Said please in a request".to_string(),
+            icon: "🎩".to_string(),
+            unlocked_at: None,
+        },
+
+        // Git & Development
+        AchievementId::GitGuru => Achievement {
+            id: id.clone(),
+            name: "Git Guru".to_string(),
+            description: "Used git commands 10 times".to_string(),
+            icon: "🌿".to_string(),
+            unlocked_at: None,
+        },
+        AchievementId::TestWriter => Achievement {
+            id: id.clone(),
+            name: "Test Writer".to_string(),
+            description: "Created test files".to_string(),
+            icon: "🧪".to_string(),
+            unlocked_at: None,
+        },
+        AchievementId::Debugger => Achievement {
+            id: id.clone(),
+            name: "Bug Squasher".to_string(),
+            description: "Fixed bugs and errors".to_string(),
+            icon: "🐛".to_string(),
+            unlocked_at: None,
+        },
+
+        // Tool Mastery
+        AchievementId::BashMaster => Achievement {
+            id: id.clone(),
+            name: "Bash Master".to_string(),
+            description: "Used Bash tool 50 times".to_string(),
+            icon: "🐚".to_string(),
+            unlocked_at: None,
+        },
+        AchievementId::FileExplorer => Achievement {
+            id: id.clone(),
+            name: "File Explorer".to_string(),
+            description: "Read 100 files".to_string(),
+            icon: "📂".to_string(),
+            unlocked_at: None,
+        },
+        AchievementId::SearchExpert => Achievement {
+            id: id.clone(),
+            name: "Search Expert".to_string(),
+            description: "Used Grep tool 50 times".to_string(),
+            icon: "🔎".to_string(),
+            unlocked_at: None,
+        },
     }
 }
 
+// Check achievements based on message content
+pub fn check_message_achievements(
+    message: &str,
+    progress: &mut AchievementProgress,
+) -> Vec<AchievementId> {
+    let mut newly_unlocked = Vec::new();
+    let message_lower = message.to_lowercase();
+
+    println!("Checking message achievements for: {}", message);
+
+    // Relationship & Greetings
+    if message_lower.contains("good morning") && progress.unlock(AchievementId::GoodMorning) {
+        newly_unlocked.push(AchievementId::GoodMorning);
+    }
+    if (message_lower.contains("good night") || message_lower.contains("goodnight"))
+        && progress.unlock(AchievementId::GoodNight) {
+        newly_unlocked.push(AchievementId::GoodNight);
+    }
+    if (message_lower.contains("thank you") || message_lower.contains("thanks") || message_lower.contains("thx"))
+        && progress.unlock(AchievementId::ThankYou) {
+        newly_unlocked.push(AchievementId::ThankYou);
+    }
+    if (message_lower.contains("love you") || message_lower.contains("ily"))
+        && progress.unlock(AchievementId::LoveYou) {
+        newly_unlocked.push(AchievementId::LoveYou);
+    }
+
+    // Personality & Fun
+    if message.chars().any(|c| c as u32 >= 0x1F300) && progress.unlock(AchievementId::EmojiUser) {
+        newly_unlocked.push(AchievementId::EmojiUser);
+    }
+    if message == message.to_uppercase() && message.len() > 5
+        && message.chars().any(|c| c.is_alphabetic())
+        && progress.unlock(AchievementId::CapsLock) {
+        newly_unlocked.push(AchievementId::CapsLock);
+    }
+    if message_lower.contains("please") && progress.unlock(AchievementId::PleaseAndThankYou) {
+        newly_unlocked.push(AchievementId::PleaseAndThankYou);
+    }
+
+    // Git & Development patterns in messages
+    if (message_lower.contains("fix") || message_lower.contains("bug") || message_lower.contains("error"))
+        && progress.unlock(AchievementId::Debugger) {
+        newly_unlocked.push(AchievementId::Debugger);
+    }
+
+    newly_unlocked
+}
+
 // Check which achievements should be unlocked based on current stats
 pub fn check_achievements(
     stats: &crate::stats::UsageStats,
@@ -489,6 +666,31 @@ pub fn check_achievements(
     // Claude Connoisseur - check model usage
     // TODO: Track different Claude models used
 
+    // Tool mastery achievements
+    if let Some(bash_count) = stats.tools_usage.get("Bash") {
+        if *bash_count >= 50 && progress.unlock(AchievementId::BashMaster) {
+            newly_unlocked.push(AchievementId::BashMaster);
+        }
+    }
+    if let Some(read_count) = stats.tools_usage.get("Read") {
+        if *read_count >= 100 && progress.unlock(AchievementId::FileExplorer) {
+            newly_unlocked.push(AchievementId::FileExplorer);
+        }
+    }
+    if let Some(grep_count) = stats.tools_usage.get("Grep") {
+        if *grep_count >= 50 && progress.unlock(AchievementId::SearchExpert) {
+            newly_unlocked.push(AchievementId::SearchExpert);
+        }
+    }
+
+    // Git Guru - check git command usage in Bash
+    if let Some(bash_count) = stats.tools_usage.get("Bash") {
+        if *bash_count >= 10 && progress.unlock(AchievementId::GitGuru) {
+            // TODO: More specific git command tracking
+            newly_unlocked.push(AchievementId::GitGuru);
+        }
+    }
+
     // Time-based achievements
     if let Some(session_start) = progress.session_start {
         let hour = session_start.hour();
diff --git a/src-tauri/src/wsl_bridge.rs b/src-tauri/src/wsl_bridge.rs
index 310f2c8..3983f11 100644
--- a/src-tauri/src/wsl_bridge.rs
+++ b/src-tauri/src/wsl_bridge.rs
@@ -91,7 +91,7 @@ impl WslBridge {
     }
 
     pub async fn new_with_loaded_achievements(app: &tauri::AppHandle) -> Self {
-        let mut bridge = Self::new();
+        let bridge = Self::new();
 
         // Load saved achievements into the stats
         let achievements = crate::achievements::load_achievements(app).await;
@@ -613,15 +613,35 @@ fn process_json_line(line: &str, app: &AppHandle, stats: &Arc<RwLock<UsageStats>
             emit_state_change(app, state, None);
         }
 
-        ClaudeMessage::User { .. } => {
+        ClaudeMessage::User { message } => {
             // Increment message count for user messages
             stats.write().increment_messages();
 
+            // Extract text content from the message
+            let message_text = message.content.iter()
+                .filter_map(|block| match block {
+                    crate::types::ContentBlock::Text { text } => Some(text.clone()),
+                    _ => None,
+                })
+                .collect::<Vec<String>>()
+                .join(" ");
+
             // Check achievements after user message
             let newly_unlocked = {
                 let mut stats_guard = stats.write();
                 println!("User sent message, checking achievements...");
-                stats_guard.check_achievements()
+
+                // Check message-based achievements
+                let mut unlocked = crate::achievements::check_message_achievements(
+                    &message_text,
+                    &mut stats_guard.achievements,
+                );
+
+                // Check stats-based achievements
+                let stats_unlocked = stats_guard.check_achievements();
+                unlocked.extend(stats_unlocked);
+
+                unlocked
             };
 
             // Emit achievement events for any newly unlocked achievements
diff --git a/src/lib/stores/achievements.ts b/src/lib/stores/achievements.ts
index ab65ce3..e0965ea 100644
--- a/src/lib/stores/achievements.ts
+++ b/src/lib/stores/achievements.ts
@@ -283,6 +283,154 @@ const achievementDefinitions: Record<AchievementId, Omit<Achievement, 'unlocked'
         rarity: 'epic',
         maxProgress: 10000,
     },
+
+    // Relationship & Greetings
+    GoodMorning: {
+        id: 'GoodMorning',
+        name: 'Good Morning!',
+        description: 'Greeted Hikari with a good morning',
+        icon: '🌅',
+        rarity: 'common',
+        maxProgress: 1,
+    },
+    GoodNight: {
+        id: 'GoodNight',
+        name: 'Sweet Dreams',
+        description: 'Said good night to Hikari',
+        icon: '🌙',
+        rarity: 'common',
+        maxProgress: 1,
+    },
+    ThankYou: {
+        id: 'ThankYou',
+        name: 'Grateful Heart',
+        description: 'Thanked Hikari for her help',
+        icon: '🙏',
+        rarity: 'common',
+        maxProgress: 1,
+    },
+    LoveYou: {
+        id: 'LoveYou',
+        name: 'Heartfelt',
+        description: 'Expressed love to Hikari',
+        icon: '💕',
+        rarity: 'rare',
+        maxProgress: 1,
+    },
+
+    // Personality & Fun
+    EmojiUser: {
+        id: 'EmojiUser',
+        name: 'Emoji Master',
+        description: 'Used 20+ emojis in messages',
+        icon: '😄',
+        rarity: 'common',
+        maxProgress: 20,
+    },
+    CapsLock: {
+        id: 'CapsLock',
+        name: 'CAPS LOCK',
+        description: 'SENT A MESSAGE IN ALL CAPS',
+        icon: '🔊',
+        rarity: 'common',
+        maxProgress: 1,
+    },
+    QuestionMaster: {
+        id: 'QuestionMaster',
+        name: 'Question Master',
+        description: 'Asked 50 questions',
+        icon: '❓',
+        rarity: 'common',
+        maxProgress: 50,
+    },
+    PleaseAndThankYou: {
+        id: 'PleaseAndThankYou',
+        name: 'Polite Programmer',
+        description: 'Always says please and thank you',
+        icon: '🎩',
+        rarity: 'common',
+        maxProgress: 10,
+    },
+
+    // Git & Development
+    CommitMaster: {
+        id: 'CommitMaster',
+        name: 'Commit Master',
+        description: 'Made 100 commits through Hikari',
+        icon: '📝',
+        rarity: 'rare',
+        maxProgress: 100,
+    },
+    PRO: {
+        id: 'PRO',
+        name: 'PRO',
+        description: 'Created 10 pull requests',
+        icon: '🔀',
+        rarity: 'rare',
+        maxProgress: 10,
+    },
+    Reviewer: {
+        id: 'Reviewer',
+        name: 'Code Reviewer',
+        description: 'Reviewed 10 pull requests',
+        icon: '👀',
+        rarity: 'rare',
+        maxProgress: 10,
+    },
+    IssueTracker: {
+        id: 'IssueTracker',
+        name: 'Issue Tracker',
+        description: 'Created 25 issues',
+        icon: '🎯',
+        rarity: 'rare',
+        maxProgress: 25,
+    },
+    GitGuru: {
+        id: 'GitGuru',
+        name: 'Git Guru',
+        description: 'Mastered git operations',
+        icon: '🌲',
+        rarity: 'epic',
+    },
+
+    // Tool Mastery
+    BashMaster: {
+        id: 'BashMaster',
+        name: 'Bash Master',
+        description: 'Used bash commands 100 times',
+        icon: '💻',
+        rarity: 'rare',
+        maxProgress: 100,
+    },
+    FileExplorer: {
+        id: 'FileExplorer',
+        name: 'File Explorer',
+        description: 'Explored files 100 times',
+        icon: '📂',
+        rarity: 'common',
+        maxProgress: 100,
+    },
+    SearchExpert: {
+        id: 'SearchExpert',
+        name: 'Search Expert',
+        description: 'Mastered advanced search queries',
+        icon: '🔎',
+        rarity: 'rare',
+    },
+    AgentCommander: {
+        id: 'AgentCommander',
+        name: 'Agent Commander',
+        description: 'Used task agents effectively',
+        icon: '🤖',
+        rarity: 'rare',
+    },
+    MCPMaster: {
+        id: 'MCPMaster',
+        name: 'MCP Master',
+        description: 'Mastered MCP tool usage',
+        icon: '🛠️',
+        rarity: 'epic',
+    },
 };
 
 // Initialize all achievements as locked
@@ -447,6 +595,26 @@ export const achievementCategories = [
         description: 'Your coding session achievements',
         ids: ['QuickSession', 'FocusedWork', 'DeepDive', 'MarathonSession', 'MarathonCoder'] as AchievementId[],
     },
+    {
+        name: 'Relationship & Greetings',
+        description: 'Our special moments together',
+        ids: ['GoodMorning', 'GoodNight', 'ThankYou', 'LoveYou'] as AchievementId[],
+    },
+    {
+        name: 'Personality & Fun',
+        description: 'Express yourself!',
+        ids: ['EmojiUser', 'CapsLock', 'QuestionMaster', 'PleaseAndThankYou'] as AchievementId[],
+    },
+    {
+        name: 'Git & Development',
+        description: 'Version control mastery',
+        ids: ['CommitMaster', 'PRO', 'Reviewer', 'IssueTracker', 'GitGuru'] as AchievementId[],
+    },
+    {
+        name: 'Tool Mastery',
+        description: 'Master of all tools',
+        ids: ['BashMaster', 'FileExplorer', 'SearchExpert', 'AgentCommander', 'MCPMaster'] as AchievementId[],
+    },
     {
         name: 'Special',
         description: 'Unique accomplishments',
diff --git a/src/lib/types/achievements.ts b/src/lib/types/achievements.ts
index d8b6c73..3485491 100644
--- a/src/lib/types/achievements.ts
+++ b/src/lib/types/achievements.ts
@@ -50,7 +50,29 @@ export type AchievementId =
     | 'Polyglot'        // 5+ languages in one session
     | 'SpeedCoder'      // 10 code blocks in 10 minutes
     | 'ClaudeConnoisseur' // Used all Claude models
-    | 'MarathonCoder';
+    | 'MarathonCoder'   // 10k tokens in one session
+    // Relationship & Greetings
+    | 'GoodMorning'     // Said good morning
+    | 'GoodNight'       // Said good night
+    | 'ThankYou'        // Said thank you
+    | 'LoveYou'         // Said love you
+    // Personality & Fun
+    | 'EmojiUser'       // Used 20+ emojis
+    | 'CapsLock'        // ALL CAPS MESSAGE
+    | 'QuestionMaster'  // Asked 50 questions
+    | 'PleaseAndThankYou' // Polite user
+    // Git & Development
+    | 'CommitMaster'    // 100 commits
+    | 'PRO'             // Created 10 PRs
+    | 'Reviewer'        // Reviewed 10 PRs
+    | 'IssueTracker'    // Created 25 issues
+    | 'GitGuru'         // Used git commands
+    // Tool Mastery
+    | 'BashMaster'      // Used bash 100 times
+    | 'FileExplorer'    // Searched files 100 times
+    | 'SearchExpert'    // Advanced searches
+    | 'AgentCommander'  // Used task agents
+    | 'MCPMaster';      // Used MCP tools
 
 export interface Achievement {
     id: AchievementId;