diff --git a/internal/webserver/handler_messages.go b/internal/webserver/handler_messages.go
index a697a13..70ca5d6 100644
--- a/internal/webserver/handler_messages.go
+++ b/internal/webserver/handler_messages.go
@@ -27,7 +27,7 @@ func (t MessageData) FocusedTweetID() scraper.TweetID {
 }
 
 func (app *Application) Messages(w http.ResponseWriter, r *http.Request) {
-	app.traceLog.Printf("'Lists' handler (path: %q)", r.URL.Path)
+	app.traceLog.Printf("'Messages' handler (path: %q)", r.URL.Path)
 
 	// TODO: what if no active user?
 
diff --git a/internal/webserver/static/styles.css b/internal/webserver/static/styles.css
index 64219eb..8ebc8bb 100644
--- a/internal/webserver/static/styles.css
+++ b/internal/webserver/static/styles.css
@@ -148,12 +148,15 @@ a.entity {
     color: var(--color-twitter-blue);
 }
 
-.tweet .text {
+.tweet .text, .dm-message-text-container .text {
     display: block;
     margin-bottom: 0.4em;
     margin-top: 0;
     overflow-wrap: anywhere;
 }
+.dm-message-text-container .text:last-child {
+    margin-bottom: 0;
+}
 #focused-tweet .text {
     font-size: 1.4em;
 }
@@ -651,39 +654,57 @@ ul.dropdown-items {
     box-sizing: border-box;
 }
 .chats-container .chat-list {
-    width: 30%;
+    flex-basis: 0;
+    flex-grow: 4;
     display: flex;
     flex-direction: column;
     overflow-y: scroll;
 }
 .chats-container .chat-list .chat {
     border-bottom: 1px solid var(--color-outline-gray);
-    padding: 0.5em;
+    padding: 1em 1em 0 1em;
     box-sizing: border-box;
+    cursor: pointer;
 }
+.chats-container .chat-list .chat .chat-preview-header {
+    display: flex;
+    align-items: center;
+    justify-content: space-between;
+}
+.chats-container .chat-list .chat .chat-preview-header .posted-at {
+    margin: 0;
+}
+.chats-container .chat-list .chat .chat-preview {
+    font-size: 0.9em;
+    color: var(--color-twitter-text-gray);
+    padding: 0 1em;
+    border-left: 1px solid var(--color-outline-gray);
+}
+
 .chats-container #chat-view {
-    width: 70%;
+    flex-basis: 0;
+    flex-grow: 7;
     border-left: 1px solid var(--color-outline-gray);
     overflow-y: scroll;
     padding: 0.5em;
     box-sizing: border-box;
 }
 .chats-container #chat-view .our-message {
-    justify-content: flex-end;
+    align-items: flex-end;
 }
 .dm-message-and-reacts-container {
     display: flex;
     flex-direction: column;
     margin: 1em 0;
 }
-p.dm-message-text {
+.dm-message-text-container {
     display: inline-block;
     padding: 1em;
     background-color: #ddd;
     border-radius: 1em;
     margin: 0;
 }
-.our-message p.dm-message-text {
+.our-message .dm-message-text-container {
     background-color: var(--color-twitter-blue-light);
 }
 .sender-profile-image-container {
@@ -708,3 +729,6 @@ p.dm-message-text {
 .our-message .dm-message-reactions {
     flex-direction: row-reverse;
 }
+.dm-message-and-reacts-container p.posted-at {
+    margin: 0 4.5em;
+}
diff --git a/internal/webserver/tpl/tweet_page_includes/chat_list.tpl b/internal/webserver/tpl/tweet_page_includes/chat_list.tpl
index db31cec..73a46af 100644
--- a/internal/webserver/tpl/tweet_page_includes/chat_list.tpl
+++ b/internal/webserver/tpl/tweet_page_includes/chat_list.tpl
@@ -3,14 +3,23 @@
     {{range .RoomIDs}}
       {{$room :=  (index $.Rooms .)}}
       <div class="chat" hx-get="/messages/{{$room.ID}}" hx-target="#chat-view" hx-swap="outerHTML" hx-push-url="true">
-        {{range $room.Participants}}
-          {{if (ne .UserID (active_user).ID)}}
-            <!-- This is some fuckery; I have no idea why "hx-target" is needed, but otherwise it targets the #chat-view. -->
-            <div class="click-eater" hx-trigger="click consume" hx-target="body">
-              {{template "author-info" (user .UserID)}}
-            </div>
+        <div class="chat-preview-header">
+          {{range $room.Participants}}
+            {{if (ne .UserID (active_user).ID)}}
+              <!-- This is some fuckery; I have no idea why "hx-target" is needed, but otherwise it targets the #chat-view. -->
+              <div class="click-eater" hx-trigger="click consume" hx-target="body">
+                {{template "author-info" (user .UserID)}}
+              </div>
+            {{end}}
           {{end}}
-        {{end}}
+          <div class="chat-preview-timestamp .posted-at-container">
+            <p class="posted-at">
+              {{$room.LastMessagedAt.Time.Format "Jan 2, 2006"}}
+              <br/>
+              {{$room.LastMessagedAt.Time.Format "3:04 pm"}}
+            </p>
+          </div>
+        </div>
         <p class="chat-preview">{{(index $.DMTrove.Messages $room.LastMessageID).Text}}</p>
       </div>
     {{end}}
diff --git a/internal/webserver/tpl/tweet_page_includes/chat_view.tpl b/internal/webserver/tpl/tweet_page_includes/chat_view.tpl
index b4b7bb6..09f3ee9 100644
--- a/internal/webserver/tpl/tweet_page_includes/chat_view.tpl
+++ b/internal/webserver/tpl/tweet_page_includes/chat_view.tpl
@@ -11,7 +11,7 @@
               <img class="profile-image" src="/content/{{$user.GetProfileImageLocalPath}}" />
             </a>
           </div>
-          <p class="dm-message-text">{{$message.Text}}</p>
+          <div class="dm-message-text-container">{{template "text-with-entities" $message.Text}}</div>
         </div>
         <div class="dm-message-reactions">
           {{range $message.Reactions}}
@@ -19,6 +19,9 @@
             <span title="{{$sender.DisplayName}} (@{{$sender.Handle}})">{{.Emoji}}</span>
           {{end}}
         </div>
+        <p class="posted-at">
+          {{$message.SentAt.Time.Format "Jan 2, 2006 @ 3:04 pm"}}
+        </p>
       </div>
     {{end}}
   </div>
diff --git a/pkg/persistence/dm_queries.go b/pkg/persistence/dm_queries.go
index 6f65e58..c77ac1c 100644
--- a/pkg/persistence/dm_queries.go
+++ b/pkg/persistence/dm_queries.go
@@ -1,6 +1,8 @@
 package persistence
 
 import (
+	"database/sql"
+	"errors"
 	"fmt"
 	"strings"
 
@@ -188,7 +190,10 @@ func (p Profile) GetChatRoomsPreview(id UserID) DMChatView {
 			panic(err)
 		}
 		err = p.DB.Get(&msg, q, args...)
-		if err != nil {
+		if errors.Is(err, sql.ErrNoRows) {
+			// TODO
+			fmt.Printf("No messages found in chat; skipping preview\n")
+		} else if err != nil {
 			panic(err)
 		}