diff --git a/main.py b/main.py
index cba205c..5bf6ffa 100644
--- a/main.py
+++ b/main.py
@@ -15,7 +15,7 @@ import sentry_sdk
 from discord import app_commands
 from openai import OpenAI
 
-from misc import add_message_to_memory, chat, get_allowed_users
+from misc import add_message_to_memory, chat, get_allowed_users, should_respond_without_trigger, update_trigger_time
 from settings import Settings
 
 sentry_sdk.init(
@@ -79,8 +79,17 @@ class LoviBotClient(discord.Client):
 
         lowercase_message: str = incoming_message.lower() if incoming_message else ""
         trigger_keywords: list[str] = ["lovibot", "@lovibot", "<@345000831499894795>", "grok", "@grok"]
-        if any(trigger in lowercase_message for trigger in trigger_keywords):
-            logger.info("Received message: %s from: %s", incoming_message, message.author.name)
+        has_trigger_keyword: bool = any(trigger in lowercase_message for trigger in trigger_keywords)
+        should_respond: bool = has_trigger_keyword or should_respond_without_trigger(str(message.channel.id), message.author.name)
+
+        if should_respond:
+            # Update trigger time if they used a trigger keyword
+            if has_trigger_keyword:
+                update_trigger_time(str(message.channel.id), message.author.name)
+
+            logger.info(
+                "Received message: %s from: %s (trigger: %s, recent: %s)", incoming_message, message.author.name, has_trigger_keyword, not has_trigger_keyword
+            )
 
             async with message.channel.typing():
                 try:
diff --git a/misc.py b/misc.py
index b85e2ee..9ab2395 100644
--- a/misc.py
+++ b/misc.py
@@ -23,6 +23,9 @@ logger: logging.Logger = logging.getLogger(__name__)
 # A dictionary to store recent messages per channel with a maximum length per channel
 recent_messages: dict[str, deque[tuple[str, str, datetime.datetime]]] = {}
 
+# A dictionary to track the last time each user triggered the bot in each channel
+last_trigger_time: dict[str, dict[str, datetime.datetime]] = {}
+
 
 def get_allowed_users() -> list[str]:
     """Get the list of allowed users to interact with the bot.
@@ -74,6 +77,43 @@ def get_recent_messages(channel_id: int, threshold_minutes: int = 10) -> list[tu
     return [(user, message) for user, message, timestamp in recent_messages[str(channel_id)] if timestamp > threshold]
 
 
+def update_trigger_time(channel_id: str, user: str) -> None:
+    """Update the last trigger time for a user in a specific channel.
+
+    Args:
+        channel_id: The ID of the channel.
+        user: The user who triggered the bot.
+    """
+    if channel_id not in last_trigger_time:
+        last_trigger_time[channel_id] = {}
+
+    last_trigger_time[channel_id][user] = datetime.datetime.now(tz=datetime.UTC)
+    logger.info("Updated trigger time for user %s in channel %s", user, channel_id)
+
+
+def should_respond_without_trigger(channel_id: str, user: str, threshold_seconds: int = 40) -> bool:
+    """Check if the bot should respond to a user without requiring trigger keywords.
+
+    Args:
+        channel_id: The ID of the channel.
+        user: The user who sent the message.
+        threshold_seconds: The number of seconds to consider as "recent trigger".
+
+    Returns:
+        True if the bot should respond without trigger keywords, False otherwise.
+    """
+    if channel_id not in last_trigger_time:
+        return False
+
+    last_trigger: datetime.datetime = last_trigger_time[channel_id][user]
+    threshold: datetime.datetime = datetime.datetime.now(tz=datetime.UTC) - datetime.timedelta(seconds=threshold_seconds)
+
+    should_respond: bool = last_trigger > threshold
+    logger.info("User %s in channel %s last triggered at %s, should respond without trigger: %s", user, channel_id, last_trigger, should_respond)
+
+    return should_respond
+
+
 def extra_context(current_channel: MessageableChannel | InteractionChannel | None, user: User | Member) -> str:
     """Add extra context to the chat prompt.