How to simplify the request to get the latest chats?

Question

Django

Hello to all! Looking at my old retrieve-a method of recent chats with users. This is complete trash, since several queries are made to the database, and two more cycles.

chatters = []
for message in Message.objects.filter(Q(user_from=user)|Q(user_to=user))\
        .order_by("created"):
    chatters.append(message.user_from)
    chatters.append(message.user_to)
counter = Counter(chain(chatters))
ordered = sorted(
                      set(chatters).union(chatters), 
                      key=lambda k: counter[k], 
                      reverse=True)
chatters=[]
for chatter in ordered:
    chatters.append(
        Message.objects.filter(
             Q(user_from=chatter,user_to=user)|Q(user_from=user,user_to=chatter))\
             .order_by("-created")[0])
chats = sorted(set(chatters),key=lambda k: k.created,reverse=True)

How to make it simpler, yes, so that you can pass it to the queryset Rest and add additional fields. The method works, but I understand that this is an overly loaded procedure with unnecessary movements. I think you need to use the capabilities of the database and ORM (such as distinct(), etc.)
Help, please!
Here's a shorter version:

chats = []
messages = Message.objects.filter(Q(user_from=user)|Q(user_to=user)).order_by("created")
chatters = set(messages.values_list('user_from', flat=True)).union(messages.values_list('user_to', flat=True))
for chatter in list(chain(chatters)):
  filtered = messages.filter(Q(user_from__id=chatter,user_to=user)|Q(user_from=user,user_to__id=chatter)).order_by("-created")
    if len(filtered)>0:
    	chats.append(filtered[0])