diff --git a/matchy/cogs/matcher.py b/matchy/cogs/matcher.py
index aa911c4..6db1da9 100644
--- a/matchy/cogs/matcher.py
+++ b/matchy/cogs/matcher.py
@@ -210,15 +210,28 @@ class MatcherCog(commands.Cog):
     async def run_hourly_tasks(self):
         """Run any hourly tasks we have"""
 
+        # Send a reminder for anything that will be active in 1 day
+        for (channel, _) in state.State.get_active_match_tasks(datetime.now() + timedelta(days=1)):
+            logger.info("Reminding about scheduled task in %s", channel)
+            msg_channel = self.bot.get_channel(int(channel))
+            await msg_channel.send(strings.reminder())
+
+        # Match groups for anything active right now
         for (channel, min) in state.State.get_active_match_tasks():
             logger.info("Scheduled match task triggered in %s", channel)
             msg_channel = self.bot.get_channel(int(channel))
             await match_groups_in_channel(msg_channel, min)
 
-        for (channel, _) in state.State.get_active_match_tasks(datetime.now() + timedelta(days=1)):
-            logger.info("Reminding about scheduled task in %s", channel)
+        # Send a reminder to threads for a match that happened two days ago
+        for (channel, _) in state.State.get_active_match_tasks(datetime.now() - timedelta(days=2)):
+            logger.info("Sending reminders to threads in %s", channel)
             msg_channel = self.bot.get_channel(int(channel))
-            await msg_channel.send(strings.reminder())
+            # Find any threads that need
+            for thread in msg_channel.threads:
+                # Only regard threads the bot created
+                # And that have no additional messages
+                if thread.owner.id == self.bot.user.id and thread.message_count <= 1:
+                    await thread.send(strings.thread_reminder())
 
 
 # Increment when adjusting the custom_id so we don't confuse old users
@@ -272,11 +285,14 @@ async def match_groups_in_channel(channel: discord.channel, min: int):
             strings.matched_up([m.mention for m in group]))
         # Set up a thread for this match if the bot has permissions to do so
         if channel.permissions_for(channel.guild.me).create_public_threads:
-            await channel.create_thread(
+            thread = await channel.create_thread(
                 name=strings.thread_title([m.display_name for m in group]),
                 message=message,
                 reason="Creating a matching thread")
 
+            # Send a message with a suggested time to the channel
+            await thread.send(f"{strings.thread_message()} {strings.time_suggestion()}")
+
     # Close off with a message
     await channel.send(strings.matching_done())
     # Save the groups to the history
diff --git a/matchy/cogs/strings.py b/matchy/cogs/strings.py
index a617194..258b071 100644
--- a/matchy/cogs/strings.py
+++ b/matchy/cogs/strings.py
@@ -145,6 +145,16 @@ Make sure you're /pause'd if you need to be, or /join in ASAP!""",
 ]
 
 
+@randomised
+def thread_reminder(): return [
+    "Hey friends, just checking in! No worries if you're too busy this week",
+    "Bork bork, quick reminder in case y'all forgot!",
+    "Hey matchees, how's your week going?",
+    "Hey everyone, don't forget to check in with eachother!",
+    "Quick friendly nudge, how're you all doing?",
+]
+
+
 @randomised
 def matching(): return [
     "Matchy is matching matchees...",
@@ -174,6 +184,36 @@ def matched_up(ms): return [
 ]
 
 
+@randomised
+def thread_message(): return [
+    "Hey peeps :)",
+    "How is everyone?",
+    "Bork!",
+    "Hey kiddos :)",
+    "Ahoy!",
+    "Great to see y'all here.",
+    "Icebreaker! What's your favourite pokemon?",
+    "I'm hungry, would a lasagna count as a sandwich?",
+    "What's your favourite keyboard key?",
+    "I'm confused thinking... Is a train just a sideways elevator?",
+    "Humans are weird, why do you have moustaches above your eyes?"
+]
+
+
+@randomised
+def time_suggestion(): return [
+    "Can I suggest a quick call on Wednesday?",
+    "Remember to organise a chat if you're up for it!",
+    "How about throwing something in the calendar for Friday?",
+    "Would 10am on Thursday work for people?",
+    "How about a call this afternoon?",
+    "Would a chat the start of a weekday work?",
+    "How's about organising a quick call sometime this week?",
+    "When's everyone available for a short hangout?",
+    "It's best to pick a time to drop in a call or meet up, if everyone is up for it!",
+]
+
+
 @randomised
 def thread_title(ms): return [
     f"{format_list(ms)}",
diff --git a/requirements.txt b/requirements.txt
index fdcdbe6..99d752f 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -1,8 +1,8 @@
-coverage==7.6.1
+coverage==7.6.10
 discord.py==2.4.0
 dpytest==0.7.0
 flake8==7.1.1
 pytest==8.3.3
-pytest-asyncio==0.24.0
+pytest-asyncio==0.25.2
 pytest-cov==5.0.0
 schema==0.7.7
\ No newline at end of file