diff --git a/src/tox-weechat-data.c b/src/tox-weechat-data.c
index b8ef54e..43f708a 100644
--- a/src/tox-weechat-data.c
+++ b/src/tox-weechat-data.c
@@ -120,6 +120,9 @@ tox_weechat_data_unsent_messages_json(struct t_tox_weechat_identity *identity)
          recipient;
          recipient = recipient->next_recipient)
     {
+        if (!(recipient->unsent_messages))
+            continue;
+
         char hex_id[TOX_CLIENT_ID_SIZE * 2 + 1];
         tox_weechat_bin2hex(recipient->recipient_id, TOX_CLIENT_ID_SIZE, hex_id);
 
@@ -204,9 +207,26 @@ tox_weechat_data_load_friend_requests(struct t_tox_weechat_identity *identity,
  */
 void
 tox_weechat_data_load_unsent_messages(struct t_tox_weechat_identity *identity,
-                                      json_t *friend_requests)
+                                      json_t *recipient_object)
 {
-    // TODO
+    tox_weechat_unsent_messages_free(identity);
+
+    const char *key;
+    json_t *message_array;
+    json_object_foreach(recipient_object, key, message_array)
+    {
+        uint8_t client_id[TOX_CLIENT_ID_SIZE];
+        tox_weechat_hex2bin(key, TOX_CLIENT_ID_SIZE * 2, (char *)client_id);
+
+        size_t index;
+        json_t *message;
+        json_array_foreach(message_array, index, message)
+        {
+            tox_weechat_add_unsent_message(identity,
+                                           client_id,
+                                           json_string_value(message));
+        }
+    }
 }
 
 /**
diff --git a/src/tox-weechat-friend-requests.c b/src/tox-weechat-friend-requests.c
index a3ba524..103d232 100644
--- a/src/tox-weechat-friend-requests.c
+++ b/src/tox-weechat-friend-requests.c
@@ -74,7 +74,8 @@ tox_weechat_friend_request_add(struct t_tox_weechat_identity *identity,
 void
 tox_weechat_friend_request_remove(struct t_tox_weechat_friend_request *request)
 {
-    struct t_tox_weechat_identity *identity = request->identity; if (request == identity->last_friend_request)
+    struct t_tox_weechat_identity *identity = request->identity;
+    if (request == identity->last_friend_request)
         identity->last_friend_request = request->prev_request;
 
     if (request->prev_request)
diff --git a/src/tox-weechat-messages.c b/src/tox-weechat-messages.c
index 737f7e1..e17e670 100644
--- a/src/tox-weechat-messages.c
+++ b/src/tox-weechat-messages.c
@@ -57,7 +57,7 @@ tox_weechat_unsent_message_recipient_new(struct t_tox_weechat_identity *identity
         return NULL;
 
     memcpy(recipient->recipient_id, id, TOX_CLIENT_ID_SIZE);
-
+    recipient->identity = identity;
     recipient->unsent_messages = recipient->last_unsent_message = NULL;
 
     recipient->prev_recipient = identity->last_unsent_message_recipient;
@@ -93,6 +93,7 @@ tox_weechat_add_unsent_message(struct t_tox_weechat_identity *identity,
         return;
 
     unsent_message->message = strdup(message);
+    unsent_message->recipient = recipient;
 
     unsent_message->prev_message = recipient->last_unsent_message;
     unsent_message->next_message = NULL;
@@ -105,6 +106,25 @@ tox_weechat_add_unsent_message(struct t_tox_weechat_identity *identity,
     recipient->last_unsent_message = unsent_message;
 }
 
+void
+tox_weechat_remove_unsent_message(struct t_tox_weechat_unsent_message *message)
+{
+    struct t_tox_weechat_unsent_message_recipient *recipient = message->recipient;
+    if (message == recipient->last_unsent_message)
+        recipient->last_unsent_message = message->prev_message;
+
+    if (message->prev_message)
+        message->prev_message->next_message = message->next_message;
+    else
+        recipient->unsent_messages = message->next_message;
+
+    if (message->next_message)
+        message->next_message->prev_message = message->prev_message;
+
+    free(message->message);
+    free(message);
+}
+
 /**
  * Sends a message to a friend. Does message splitting and queuing.
  */
@@ -128,3 +148,22 @@ tox_weechat_send_friend_message(struct t_tox_weechat_identity *identity,
     return rc;
 }
 
+void
+tox_weechat_unsent_messages_free(struct t_tox_weechat_identity *identity)
+{
+    struct t_tox_weechat_unsent_message_recipient *recipient;
+    for (recipient = identity->unsent_message_recipients;
+         recipient;
+         recipient = recipient->next_recipient)
+    {
+        while (recipient->unsent_messages)
+            tox_weechat_remove_unsent_message(recipient->unsent_messages);
+    }
+}
+
+void
+tox_weechat_attempt_message_flush(struct t_tox_weechat_identity *identity,
+                                  int32_t friend_number)
+{
+
+}
diff --git a/src/tox-weechat-messages.h b/src/tox-weechat-messages.h
index 8ebc743..88f9e46 100644
--- a/src/tox-weechat-messages.h
+++ b/src/tox-weechat-messages.h
@@ -27,6 +27,7 @@ struct t_tox_weechat_identity;
 struct t_tox_weechat_unsent_message_recipient
 {
     uint8_t recipient_id[TOX_CLIENT_ID_SIZE];
+    struct t_tox_weechat_identity *identity;
 
     struct t_tox_weechat_unsent_message *unsent_messages;
     struct t_tox_weechat_unsent_message *last_unsent_message;
@@ -37,7 +38,8 @@ struct t_tox_weechat_unsent_message_recipient
 
 struct t_tox_weechat_unsent_message
 {
-    const char *message;
+    char *message;
+    struct t_tox_weechat_unsent_message_recipient *recipient;
 
     struct t_tox_weechat_unsent_message *next_message;
     struct t_tox_weechat_unsent_message *prev_message;
@@ -53,4 +55,7 @@ tox_weechat_add_unsent_message(struct t_tox_weechat_identity *identity,
                                const uint8_t *recipient_id,
                                const char *message);
 
+void
+tox_weechat_unsent_messages_free(struct t_tox_weechat_identity *identity);
+
 #endif // TOX_WEECHAT_MESSAGES_H