diff --git a/backend/src/routes/friends.js b/backend/src/routes/friends.js
index 9842778..4c7aea8 100644
--- a/backend/src/routes/friends.js
+++ b/backend/src/routes/friends.js
@@ -59,7 +59,8 @@ router.get('/', authMiddleware, asyncHandler(async (req, res) => {
   const challengeFriends = await query(
     `SELECT DISTINCT
       u.id, u.username, u.email,
-      (SELECT COUNT(*) FROM predictions WHERE user_id = u.id AND status = 'validated') as total_points
+      (SELECT COUNT(*) FROM predictions WHERE user_id = u.id AND status = 'validated') as total_points,
+      (SELECT status FROM friendships WHERE (user_id = ? AND friend_id = u.id) OR (user_id = u.id AND friend_id = ?) LIMIT 1) as friendship_status
     FROM users u
     WHERE u.id IN (
       SELECT DISTINCT cp.user_id 
@@ -79,7 +80,7 @@ router.get('/', authMiddleware, asyncHandler(async (req, res) => {
     )
     ${notInClause}
     ORDER BY u.username`,
-    [req.user.userId, req.user.userId, req.user.userId, req.user.userId, req.user.userId, req.user.userId, ...friends.map(f => f.id)]
+    [req.user.userId, req.user.userId, req.user.userId, req.user.userId, req.user.userId, req.user.userId, req.user.userId, req.user.userId, ...friends.map(f => f.id)]
   );
 
   res.json({ 
diff --git a/frontend/src/pages/Friends.jsx b/frontend/src/pages/Friends.jsx
index 793a084..b927e80 100644
--- a/frontend/src/pages/Friends.jsx
+++ b/frontend/src/pages/Friends.jsx
@@ -281,12 +281,12 @@ export default function Friends() {
                       </div>
                       <div style={{ display: 'flex', gap: '0.5rem', alignItems: 'center', flexShrink: 0, flexWrap: 'nowrap' }}>
                         <button
-                          className="btn btn-primary btn-sm"
+                          className={`btn btn-sm ${friend.friendship_status === 'pending' ? 'btn-secondary' : 'btn-primary'}`}
                           onClick={() => handleSendRequest(friend.id)}
-                          disabled={sending === friend.id}
+                          disabled={sending === friend.id || friend.friendship_status === 'pending'}
                           style={{ flexShrink: 0 }}
                         >
-                          {sending === friend.id ? 'Sending...' : 'Add Friend'}
+                          {sending === friend.id ? 'Sending...' : friend.friendship_status === 'pending' ? 'Pending' : 'Add Friend'}
                         </button>
                         <div style={{ color: 'var(--primary)', whiteSpace: 'nowrap' }}>{friend.total_points} points</div>
                       </div>