diff --git a/tildes/tildes/jinja.py b/tildes/tildes/jinja.py
index 26e68b8..c32ccd6 100644
--- a/tildes/tildes/jinja.py
+++ b/tildes/tildes/jinja.py
@@ -7,7 +7,7 @@ from typing import Any
 
 from pyramid.config import Configurator
 
-from tildes.lib.datetime import descriptive_timedelta
+from tildes.lib.datetime import adaptive_date, descriptive_timedelta
 from tildes.models.comment import Comment
 from tildes.models.group import Group
 from tildes.models.topic import Topic
@@ -36,7 +36,10 @@ def includeme(config: Configurator) -> None:
     settings["jinja2.trim_blocks"] = True
 
     # add custom jinja filters
-    settings["jinja2.filters"] = {"ago": descriptive_timedelta}
+    settings["jinja2.filters"] = {
+        "adaptive_date": adaptive_date,
+        "ago": descriptive_timedelta,
+    }
 
     # add custom jinja tests
     settings["jinja2.tests"] = {
diff --git a/tildes/tildes/lib/datetime.py b/tildes/tildes/lib/datetime.py
index e97d4ce..c0aaf05 100644
--- a/tildes/tildes/lib/datetime.py
+++ b/tildes/tildes/lib/datetime.py
@@ -130,3 +130,24 @@ def descriptive_timedelta(target: datetime, abbreviate: bool = False) -> str:
         result = result.replace(",", "")
 
     return result
+
+
+def adaptive_date(target: datetime, abbreviate: bool = False) -> str:
+    """Return a date string that switches from relative to absolute past a threshold."""
+    threshold = timedelta(days=7)
+
+    # if the date is more recent than threshold, return the relative "ago"-style string
+    if utc_now() - target < threshold:
+        return descriptive_timedelta(target, abbreviate)
+
+    # if abbreviating, use the short version of month name ("Dec" instead of "December")
+    if abbreviate:
+        format_str = "%b %-d"
+    else:
+        format_str = "%B %-d"
+
+    # only append the year if it's not the current year
+    if target.year != utc_now().year:
+        format_str += ", %Y"
+
+    return target.strftime(format_str)
diff --git a/tildes/tildes/templates/macros/comments.jinja2 b/tildes/tildes/templates/macros/comments.jinja2
index 2657bad..e36b82d 100644
--- a/tildes/tildes/templates/macros/comments.jinja2
+++ b/tildes/tildes/templates/macros/comments.jinja2
@@ -1,7 +1,7 @@
 {# Copyright (c) 2018 Tildes contributors <code@tildes.net> #}
 {# SPDX-License-Identifier: AGPL-3.0-or-later #}
 
-{% from 'datetime.jinja2' import time_ago_responsive %}
+{% from 'datetime.jinja2' import adaptive_date_responsive %}
 {% from 'links.jinja2' import username_linked %}
 
 {% macro render_single_comment(comment) %}
@@ -57,11 +57,11 @@
           </span>
         {% endif %}
 
-        {{ time_ago_responsive(comment.created_time, class_="comment-posted-time") }}
+        {{ adaptive_date_responsive(comment.created_time, class_="comment-posted-time") }}
 
         {% if comment.last_edited_time %}
           <span class="comment-edited-time">
-            (edited {{ time_ago_responsive(comment.last_edited_time) }})
+            (edited {{ adaptive_date_responsive(comment.last_edited_time) }})
           </span>
         {% endif %}
       {% else %}
diff --git a/tildes/tildes/templates/macros/datetime.jinja2 b/tildes/tildes/templates/macros/datetime.jinja2
index 0ddf716..80b31d2 100644
--- a/tildes/tildes/templates/macros/datetime.jinja2
+++ b/tildes/tildes/templates/macros/datetime.jinja2
@@ -1,19 +1,15 @@
 {# Copyright (c) 2018 Tildes contributors <code@tildes.net> #}
 {# SPDX-License-Identifier: AGPL-3.0-or-later #}
 
-{% macro time_ago(datetime) -%}
-<time datetime="{{ datetime.strftime('%Y-%m-%dT%H:%M:%SZ') }}" title="{{ datetime.strftime('%Y-%m-%d %H:%M:%S UTC') }}">{{ datetime|ago }}</time>
+{% macro time_ago(datetime, abbreviate=False) -%}
+<time datetime="{{ datetime.strftime('%Y-%m-%dT%H:%M:%SZ') }}" title="{{ datetime.strftime('%Y-%m-%d %H:%M:%S UTC') }}">{{ datetime|ago(abbreviate) }}</time>
 {%- endmacro %}
 
-{% macro time_ago_abbreviated(datetime) -%}
-<time datetime="{{ datetime.strftime('%Y-%m-%dT%H:%M:%SZ') }}" title="{{ datetime.strftime('%Y-%m-%d %H:%M:%S UTC') }}">{{ datetime|ago(abbreviate=True) }}</time>
-{%- endmacro %}
-
-{% macro time_ago_responsive(datetime, class_=None) -%}
+{% macro adaptive_date_responsive(datetime, class_=None) -%}
 <time
   class="time-responsive{{ ' '+class_ if class_ else '' }}"
   datetime="{{ datetime.strftime('%Y-%m-%dT%H:%M:%SZ') }}"
   title="{{ datetime.strftime('%Y-%m-%d %H:%M:%S UTC') }}"
-  data-abbreviated="{{ datetime|ago(abbreviate=True) }}"
-><span class="time-responsive-full">{{ datetime|ago(abbreviate=False) }}</span></time>
+  data-abbreviated="{{ datetime|adaptive_date(abbreviate=True) }}"
+><span class="time-responsive-full">{{ datetime|adaptive_date(abbreviate=False) }}</span></time>
 {%- endmacro %}
diff --git a/tildes/tildes/templates/macros/messages.jinja2 b/tildes/tildes/templates/macros/messages.jinja2
index 7b81726..2896e1d 100644
--- a/tildes/tildes/templates/macros/messages.jinja2
+++ b/tildes/tildes/templates/macros/messages.jinja2
@@ -1,7 +1,7 @@
 {# Copyright (c) 2018 Tildes contributors <code@tildes.net> #}
 {# SPDX-License-Identifier: AGPL-3.0-or-later #}
 
-{% from 'macros/datetime.jinja2' import time_ago %}
+{% from 'macros/datetime.jinja2' import adaptive_date_responsive %}
 {% from 'macros/links.jinja2' import username_linked %}
 
 {% macro render_message(message) %}
@@ -13,7 +13,7 @@
 
     <header>
       {{ username_linked(message.sender.username) }}
-      {{ time_ago(message.created_time) }}
+      {{ adaptive_date_responsive(message.created_time) }}
     </header>
 
     <div class="message-text"
diff --git a/tildes/tildes/templates/macros/topics.jinja2 b/tildes/tildes/templates/macros/topics.jinja2
index 47d773f..5e3faaf 100644
--- a/tildes/tildes/templates/macros/topics.jinja2
+++ b/tildes/tildes/templates/macros/topics.jinja2
@@ -1,7 +1,7 @@
 {# Copyright (c) 2018 Tildes contributors <code@tildes.net> #}
 {# SPDX-License-Identifier: AGPL-3.0-or-later #}
 
-{% from 'macros/datetime.jinja2' import time_ago_responsive %}
+{% from 'macros/datetime.jinja2' import adaptive_date_responsive %}
 {% from 'macros/links.jinja2' import group_linked, username_linked %}
 
 {% macro render_topic_for_listing(topic, show_group=False, rank=None) %}
@@ -78,7 +78,7 @@
 
       <div aria-label="Posted by">{{ username_linked(topic.user.username) }}</div>
 
-      <div aria-label="Post time">{{ time_ago_responsive(topic.created_time) }}</div>
+      <div aria-label="Post time">{{ adaptive_date_responsive(topic.created_time) }}</div>
     </footer>
 
     {{ topic_voting(topic) }}
diff --git a/tildes/tildes/templates/messages.jinja2 b/tildes/tildes/templates/messages.jinja2
index 660edd9..f969de7 100644
--- a/tildes/tildes/templates/messages.jinja2
+++ b/tildes/tildes/templates/messages.jinja2
@@ -3,7 +3,7 @@
 
 {% extends 'base_user_menu.jinja2' %}
 
-{% from 'macros/datetime.jinja2' import time_ago_responsive %}
+{% from 'macros/datetime.jinja2' import adaptive_date_responsive %}
 {% from 'macros/links.jinja2' import username_linked %}
 
 {% block title %}Message Inbox{% endblock %}
@@ -31,7 +31,7 @@
         <a href="{{ request.route_url('message_conversation', conversation_id36=conversation.conversation_id36) }}">{{ conversation.subject }}</a>
       </td>
       <td>{{ username_linked(conversation.other_user(request.user).username) }}</td>
-      <td class="text-right">{{ time_ago_responsive(conversation.last_activity_time) }}</td>
+      <td class="text-right">{{ adaptive_date_responsive(conversation.last_activity_time) }}</td>
       <td class="text-right">{{ conversation.num_replies + 1 }}</td>
     </tr>
   {% endfor %}
diff --git a/tildes/tildes/templates/topic.jinja2 b/tildes/tildes/templates/topic.jinja2
index 211ea03..615b4fa 100644
--- a/tildes/tildes/templates/topic.jinja2
+++ b/tildes/tildes/templates/topic.jinja2
@@ -4,7 +4,7 @@
 {% extends 'base.jinja2' %}
 
 {% from 'macros/comments.jinja2' import comment_label_options_template, render_comment_tree with context %}
-{% from 'macros/datetime.jinja2' import time_ago, time_ago_abbreviated, time_ago_responsive %}
+{% from 'macros/datetime.jinja2' import adaptive_date_responsive, time_ago %}
 {% from 'macros/forms.jinja2' import markdown_textarea %}
 {% from 'macros/links.jinja2' import group_linked, username_linked %}
 {% from 'macros/topics.jinja2' import topic_voting with context %}
@@ -20,7 +20,7 @@
 <header>
   {{ topic_voting(topic) }}
   <h1>{{ topic.title }}</h1>
-  <div class="topic-full-byline">Posted {{ time_ago_responsive(topic.created_time) }} by
+  <div class="topic-full-byline">Posted {{ adaptive_date_responsive(topic.created_time) }} by
     {% if request.has_permission('view_author', topic) %}
       {{ username_linked(topic.user.username) }}
     {% else %}
@@ -29,7 +29,7 @@
 
     {% if topic.last_edited_time %}
       <span class="text-italic">
-        (edited {{ time_ago_responsive(topic.last_edited_time) }})
+        (edited {{ adaptive_date_responsive(topic.last_edited_time) }})
       </span>
     {% endif %}
   </div>
@@ -306,7 +306,7 @@
     <dt>Last comment posted</dt>
     <dd>
       <a href="{{ comments.most_recent_comment.permalink }}" data-js-hide-sidebar-no-preventdefault>
-        {{ time_ago(topic.last_activity_time) }}
+        {{ adaptive_date_responsive(topic.last_activity_time) }}
       </a>
     </dd>
   {% else %}
@@ -326,7 +326,7 @@
               {{ username_linked(entry.user) }}
             {% endif %}
             {{ entry }}
-            <span class="topic-log-entry-time">({{ time_ago_abbreviated(entry.event_time) }})</span>
+            <span class="topic-log-entry-time">({{ time_ago(entry.event_time, abbreviate=True) }})</span>
           </li>
         {% endfor %}
         </ol>