Sql query for creating message list - php

Question

I am creating a message service with Laravel.
I want to display recent messages from all based on time. This is what I am trying to implement
The following are my tables
message table
message_user table
I tried the following code
SELECT DISTINCT user_id,sender
FROM (
SELECT DISTINCT message_user.user_id, messages.sender, messages.created_at
FROM messages
JOIN message_user ON message_user.message_id=messages.id AND message_user.user_id=225
UNION
SELECT DISTINCT message_user.user_id, messages.sender, messages.created_at FROM messages
JOIN message_user ON message_user.message_id=messages.id AND messages.sender=225 AND message_user.user_id NOT IN (
SELECT DISTINCT messages.sender
FROM messages
JOIN message_user ON message_user.message_id=messages.id AND message_user.user_id=225
)
) mytable
ORDER BY created_at
The problem is that the output is not in the expected format (that is not sorted based on created_at)
Following is the corresponding Laravel code I have tried
$id = $request->user()->id;
$user = User::find($id);
$buddylist = $user->messages()->select(DB::raw('message_user.user_id,messages.sender,messages.created_at'));
$subquery = Message::select(DB::raw(' messages.sender'))->join('message_user','messages.id','=','message_user.message_id') ->where("message_user.user_id",'=',$request->user()->id);
$mybuddy = Message::selectRaw('message_user.user_id,messages.sender,messages.created_at')
->join('message_user','messages.id','=','message_user.message_id')
->where("messages.sender",'=',$request->user()->id)
->whereNotIn('message_user.user_id', $subquery)
->union( $buddylist)
->groupBy('sender')
->groupBy('user_id')
->orderBy('created_at','desc')
->get();

Answer 1

If you have another column named 'receiver_id' what you could do is:
$query="select * from messages WHERE sender_id='user_id' or receiver_id='user_id' ORDER BY created_at asc";