diff --git a/lib/philomena/conversations.ex b/lib/philomena/conversations.ex
index 9f91a3b3..7b5d4e9d 100644
--- a/lib/philomena/conversations.ex
+++ b/lib/philomena/conversations.ex
@@ -4,23 +4,11 @@ defmodule Philomena.Conversations do
   """
 
   import Ecto.Query, warn: false
+  alias Ecto.Multi
   alias Philomena.Repo
 
   alias Philomena.Conversations.Conversation
 
-  @doc """
-  Returns the list of conversations.
-
-  ## Examples
-
-      iex> list_conversations()
-      [%Conversation{}, ...]
-
-  """
-  def list_conversations do
-    Repo.all(Conversation)
-  end
-
   @doc """
   Gets a single conversation.
 
@@ -49,9 +37,9 @@ defmodule Philomena.Conversations do
       {:error, %Ecto.Changeset{}}
 
   """
-  def create_conversation(attrs \\ %{}) do
+  def create_conversation(from, attrs \\ %{}) do
     %Conversation{}
-    |> Conversation.changeset(attrs)
+    |> Conversation.creation_changeset(from, attrs)
     |> Repo.insert()
   end
 
@@ -117,20 +105,19 @@ defmodule Philomena.Conversations do
     |> Repo.aggregate(:count, :id)
   end
 
-  alias Philomena.Conversations.Message
-
-  @doc """
-  Returns the list of messages.
-
-  ## Examples
-
-      iex> list_messages()
-      [%Message{}, ...]
-
-  """
-  def list_messages do
-    Repo.all(Message)
+  def mark_conversation_read(%Conversation{to_id: user_id} = conversation, %{id: user_id}) do
+    conversation
+    |> Conversation.read_changeset(%{to_read: true})
+    |> Repo.update()
   end
+  def mark_conversation_read(%Conversation{from_id: user_id} = conversation, %{id: user_id}) do
+    conversation
+    |> Conversation.read_changeset(%{from_read: true})
+    |> Repo.update()
+  end
+  def mark_conversation_read(_conversation, _user), do: {:ok, nil}
+
+  alias Philomena.Conversations.Message
 
   @doc """
   Gets a single message.
@@ -160,10 +147,21 @@ defmodule Philomena.Conversations do
       {:error, %Ecto.Changeset{}}
 
   """
-  def create_message(attrs \\ %{}) do
-    %Message{}
-    |> Message.changeset(attrs)
-    |> Repo.insert()
+  def create_message(conversation, user, attrs \\ %{}) do
+    message =
+      Ecto.build_assoc(conversation, :messages)
+      |> Message.creation_changeset(attrs, user)
+
+    conversation_query =
+      Conversation
+      |> where(id: ^conversation.id)
+
+    now = DateTime.utc_now()
+
+    Multi.new
+    |> Multi.insert(:message, message)
+    |> Multi.update_all(:conversation, conversation_query, set: [from_read: false, to_read: false, last_message_at: now])
+    |> Repo.isolated_transaction(:serializable)
   end
 
   @doc """
diff --git a/lib/philomena/conversations/conversation.ex b/lib/philomena/conversations/conversation.ex
index 5e82630b..62ddbed2 100644
--- a/lib/philomena/conversations/conversation.ex
+++ b/lib/philomena/conversations/conversation.ex
@@ -3,12 +3,15 @@ defmodule Philomena.Conversations.Conversation do
   import Ecto.Changeset
 
   alias Philomena.Users.User
+  alias Philomena.Conversations.Message
+  alias Philomena.Repo
 
   @derive {Phoenix.Param, key: :slug}
 
   schema "conversations" do
     belongs_to :from, User
     belongs_to :to, User
+    has_many :messages, Message
 
     field :title, :string
     field :to_read, :boolean, default: false
@@ -16,7 +19,8 @@ defmodule Philomena.Conversations.Conversation do
     field :to_hidden, :boolean, default: false
     field :from_hidden, :boolean, default: false
     field :slug, :string
-    field :last_message_at, :naive_datetime
+    field :last_message_at, :utc_datetime
+    field :recipient, :string, virtual: true
 
     timestamps(inserted_at: :created_at)
   end
@@ -27,4 +31,41 @@ defmodule Philomena.Conversations.Conversation do
     |> cast(attrs, [])
     |> validate_required([])
   end
+
+  def read_changeset(conversation, attrs) do
+    conversation
+    |> cast(attrs, [:from_read, :to_read])
+  end
+
+  @doc false
+  def creation_changeset(conversation, from, attrs) do
+    conversation
+    |> cast(attrs, [:title, :recipient])
+    |> validate_required([:title, :recipient])
+    |> validate_length(:title, max: 300, count: :bytes)
+    |> put_assoc(:from, from)
+    |> put_recipient()
+    |> set_slug()
+    |> set_last_message()
+    |> cast_assoc(:messages, with: {Message, :creation_changeset, [from]})
+  end
+
+  defp set_slug(changeset) do
+    changeset
+    |> change(slug: Ecto.UUID.generate())
+  end
+
+  defp set_last_message(changeset) do
+    changeset
+    |> change(last_message_at: DateTime.utc_now() |> DateTime.truncate(:second))
+  end
+
+  defp put_recipient(changeset) do
+    recipient = changeset |> get_field(:recipient)
+    user = Repo.get_by(User, name: recipient) |> IO.inspect()
+
+    changeset
+    |> put_change(:to, user)
+    |> validate_required(:to)
+  end
 end
diff --git a/lib/philomena/conversations/message.ex b/lib/philomena/conversations/message.ex
index 7ee9c008..80ac7487 100644
--- a/lib/philomena/conversations/message.ex
+++ b/lib/philomena/conversations/message.ex
@@ -20,4 +20,13 @@ defmodule Philomena.Conversations.Message do
     |> cast(attrs, [])
     |> validate_required([])
   end
+
+  @doc false
+  def creation_changeset(message, attrs, user) do
+    message
+    |> cast(attrs, [:body])
+    |> validate_required([:body])
+    |> put_assoc(:from, user)
+    |> validate_length(:body, max: 300_000, count: :bytes)
+  end
 end
diff --git a/lib/philomena_web/controllers/conversation/message_controller.ex b/lib/philomena_web/controllers/conversation/message_controller.ex
new file mode 100644
index 00000000..95145c44
--- /dev/null
+++ b/lib/philomena_web/controllers/conversation/message_controller.ex
@@ -0,0 +1,37 @@
+defmodule PhilomenaWeb.Conversation.MessageController do
+  use PhilomenaWeb, :controller
+
+  alias Philomena.Conversations.{Conversation, Message}
+  alias Philomena.Conversations
+  alias Philomena.Repo
+  import Ecto.Query
+
+  plug PhilomenaWeb.FilterBannedUsersPlug
+  plug :load_and_authorize_resource, model: Conversation, id_name: "conversation_id", id_field: "slug", persisted: true
+
+  def create(conn, %{"message" => message_params}) do
+    conversation = conn.assigns.conversation
+    user = conn.assigns.current_user
+
+    case Conversations.create_message(conversation, user, message_params) do
+      {:ok, _result} ->
+        count =
+          Message
+          |> where(conversation_id: ^conversation.id)
+          |> Repo.aggregate(:count, :id)
+
+        page =
+          Float.ceil(count / 25)
+          |> round()
+
+        conn
+        |> put_flash(:info, "Message successfully sent.")
+        |> redirect(to: Routes.conversation_path(conn, :show, conversation, page: page))
+
+      _error ->
+        conn
+        |> put_flash(:error, "There was an error posting your message")
+        |> redirect(external: conn.assigns.referrer)
+    end
+  end
+end
\ No newline at end of file
diff --git a/lib/philomena_web/controllers/conversation_controller.ex b/lib/philomena_web/controllers/conversation_controller.ex
index d4ffb4d9..8750180d 100644
--- a/lib/philomena_web/controllers/conversation_controller.ex
+++ b/lib/philomena_web/controllers/conversation_controller.ex
@@ -1,7 +1,7 @@
 defmodule PhilomenaWeb.ConversationController do
   use PhilomenaWeb, :controller
 
-  alias Philomena.Conversations.{Conversation, Message}
+  alias Philomena.{Conversations, Conversations.Conversation, Conversations.Message}
   alias Philomena.Textile.Renderer
   alias Philomena.Repo
   import Ecto.Query
@@ -24,6 +24,7 @@ defmodule PhilomenaWeb.ConversationController do
 
   def show(conn, _params) do
     conversation = conn.assigns.conversation
+    user = conn.assigns.current_user
 
     messages =
       Message
@@ -39,6 +40,38 @@ defmodule PhilomenaWeb.ConversationController do
     messages =
       %{messages | entries: Enum.zip(messages.entries, rendered)}
 
-    render(conn, "show.html", conversation: conversation, messages: messages)
+    changeset =
+      %Message{}
+      |> Conversations.change_message()
+
+    conversation
+    |> Conversations.mark_conversation_read(user)
+
+    render(conn, "show.html", conversation: conversation, messages: messages, changeset: changeset)
+  end
+
+  def new(conn, params) do
+    changeset =
+      %Conversation{recipient: params["recipient"], messages: [%Message{}]}
+      |> Conversations.change_conversation()
+
+    render(conn, "new.html", changeset: changeset)
+  end
+
+  # Somewhat annoying, cast_assoc has no "limit" validation so we force it
+  # here to require exactly 1
+  def create(conn, %{"conversation" => %{"messages" => %{"0" => _message_params}} = conversation_params}) do
+    user = conn.assigns.current_user
+
+    case Conversations.create_conversation(user, conversation_params) do
+      {:ok, conversation} ->
+        conn
+        |> put_flash(:info, "Conversation successfully created.")
+        |> redirect(to: Routes.conversation_path(conn, :show, conversation))
+
+      {:error, changeset} ->
+        conn
+        |> render("new.html", changeset: changeset)
+    end
   end
 end
\ No newline at end of file
diff --git a/lib/philomena_web/router.ex b/lib/philomena_web/router.ex
index 4c512638..5773bfc1 100644
--- a/lib/philomena_web/router.ex
+++ b/lib/philomena_web/router.ex
@@ -55,7 +55,9 @@ defmodule PhilomenaWeb.Router do
     pipe_through [:browser, :ensure_totp, :protected]
 
     resources "/notifications", NotificationController, only: [:index, :delete]
-    resources "/conversations", ConversationController, only: [:index, :show]
+    resources "/conversations", ConversationController, only: [:index, :show, :new, :create] do
+      resources "/messages", Conversation.MessageController, only: [:create]
+    end
     resources "/images", ImageController, only: [] do
       resources "/vote", Image.VoteController, only: [:create, :delete], singleton: true
       resources "/fave", Image.FaveController, only: [:create, :delete], singleton: true
diff --git a/lib/philomena_web/templates/conversation/index.html.slime b/lib/philomena_web/templates/conversation/index.html.slime
index d64bf3e8..0cbc991c 100644
--- a/lib/philomena_web/templates/conversation/index.html.slime
+++ b/lib/philomena_web/templates/conversation/index.html.slime
@@ -5,6 +5,10 @@ elixir:
 h1 My Conversations
 .block
   .block__header
+    a href=Routes.conversation_path(@conn, :new)
+      i.fa.fa-paper-plane>
+      ' Create New Conversation
+
     = pagination
 
   .block__content
@@ -16,7 +20,7 @@ h1 My Conversations
           th.table--communication-list__options Options
       tbody
         = for c <- @conversations do
-          tr
+          tr class=conversation_class(@conn.assigns.current_user, c)
             td.table--communication-list__name
               => link c.title, to: Routes.conversation_path(@conn, :show, c)
 
diff --git a/lib/philomena_web/templates/conversation/message/_form.html.slime b/lib/philomena_web/templates/conversation/message/_form.html.slime
new file mode 100644
index 00000000..d8de7f2a
--- /dev/null
+++ b/lib/philomena_web/templates/conversation/message/_form.html.slime
@@ -0,0 +1,19 @@
+= form_for @changeset, Routes.conversation_message_path(@conn, :create, @conversation), fn f ->
+  .block
+    .block__header.block__header--js-tabbed
+      a.selected href="#" data-click-tab="write"
+        i.fa.fa-pencil-alt>
+        | Reply
+
+      a href="#" data-click-tab="preview"
+        i.fa.fa-eye>
+        | Preview
+
+    .block__tab.communication-edit__tab.selected data-tab="write"
+      = textarea f, :body, class: "input input--wide input--text js-preview-input js-toolbar-input", placeholder: "Your message", required: true
+
+    .block__tab.communication-edit__tab.hidden data-tab="preview"
+      | [Loading preview...]
+
+    .block__content.communication-edit__actions
+      = submit "Send", class: "button", autocomplete: "off", data: [disable_with: "Sending..."]
diff --git a/lib/philomena_web/templates/conversation/new.html.slime b/lib/philomena_web/templates/conversation/new.html.slime
new file mode 100644
index 00000000..3da0a3da
--- /dev/null
+++ b/lib/philomena_web/templates/conversation/new.html.slime
@@ -0,0 +1,41 @@
+h1 New Conversation
+.block
+  .block__header
+    => link "Conversations", to: Routes.conversation_path(@conn, :index)
+    ' &raquo;
+    span.block__header__title New Conversation
+
+= form_for @changeset, Routes.conversation_path(@conn, :create), fn f ->
+  = if @changeset.action do
+    .alert.alert-danger
+      p Oops, something went wrong! Please check the errors below.
+
+  .field
+    .fieldlabel Specify any user's exact name here, case-sensitive
+    = text_input f, :recipient, class: "input input--wide", placeholder: "Recipient", required: true
+    = error_tag f, :to
+
+  .field
+    = text_input f, :title, class: "input input--wide", placeholder: "Title", required: true
+    = error_tag f, :title
+
+  = inputs_for f, :messages, fn fm ->
+    .block
+      .block__header.block__header--js-tabbed
+        a.selected href="#" data-click-tab="write"
+          i.fa.fa-pencil-alt>
+          | Reply
+
+        a href="#" data-click-tab="preview"
+          i.fa.fa-eye>
+          | Preview
+
+      .block__tab.communication-edit__tab.selected data-tab="write"
+        = textarea fm, :body, class: "input input--wide input--text js-preview-input js-toolbar-input", placeholder: "Your message", required: true
+        = error_tag fm, :body
+
+      .block__tab.communication-edit__tab.hidden data-tab="preview"
+        | [Loading preview...]
+
+  .block__content.communication-edit__actions
+    = submit "Send", class: "button", autocomplete: "off", data: [disable_with: "Sending..."]
\ No newline at end of file
diff --git a/lib/philomena_web/templates/conversation/show.html.slime b/lib/philomena_web/templates/conversation/show.html.slime
index c9902bd0..3863e07a 100644
--- a/lib/philomena_web/templates/conversation/show.html.slime
+++ b/lib/philomena_web/templates/conversation/show.html.slime
@@ -1,7 +1,7 @@
 elixir:
   route = fn p -> Routes.conversation_path(@conn, :show, @conversation, p) end
   pagination = render PhilomenaWeb.PaginationView, "_pagination.html", page: @messages, route: route, conn: @conn
-  other = other_party(@current_user.id, @conversation)
+  other = other_party(@current_user, @conversation)
 
 h1 = @conversation.title
 .block
@@ -20,3 +20,14 @@ h1 = @conversation.title
 .block
   .block__header.block__header--light
     = pagination
+
+= if @messages.total_entries < 1_000 do
+  = render PhilomenaWeb.Conversation.MessageView, "_form.html", conversation: @conversation, changeset: @changeset, conn: @conn
+- else
+  div
+    h2 Okay, we're impressed
+    p You've managed to send over 1,000 messages in this conversation!
+    p We'd like to ask you to make a new conversation. Don't worry, this one won't go anywhere if you need to refer back to it.
+    p
+      => link "Click here", to: Routes.conversation_path(@conn, :new, receipient: other.name)
+      ' to make a new conversation with this user.
diff --git a/lib/philomena_web/views/conversation/message_view.ex b/lib/philomena_web/views/conversation/message_view.ex
new file mode 100644
index 00000000..6dc4e279
--- /dev/null
+++ b/lib/philomena_web/views/conversation/message_view.ex
@@ -0,0 +1,3 @@
+defmodule PhilomenaWeb.Conversation.MessageView do
+  use PhilomenaWeb, :view
+end
diff --git a/lib/philomena_web/views/conversation_view.ex b/lib/philomena_web/views/conversation_view.ex
index b4c2c1d7..973656de 100644
--- a/lib/philomena_web/views/conversation_view.ex
+++ b/lib/philomena_web/views/conversation_view.ex
@@ -1,9 +1,27 @@
 defmodule PhilomenaWeb.ConversationView do
   use PhilomenaWeb, :view
 
-  def other_party(user_id, %{to_id: user_id} = conversation),
+  def other_party(%{id: user_id}, %{to_id: user_id} = conversation),
     do: conversation.from
 
-  def other_party(_user_id, conversation),
+  def other_party(_user, conversation),
     do: conversation.to
+
+
+  def read_by?(%{id: user_id}, %{to_id: user_id} = conversation),
+    do: conversation.to_read
+
+  def read_by?(%{id: user_id}, %{from_id: user_id} = conversation),
+    do: conversation.from_read
+
+  def read_by?(_user, _conversation),
+    do: false
+
+
+  def conversation_class(user, conversation) do
+    case read_by?(user, conversation) do
+      false -> "warning"
+      _     -> nil
+    end
+  end
 end
\ No newline at end of file