diff --git a/src/dolores.py b/src/dolores.py
index 56e6ae3..5eb4e71 100644
--- a/src/dolores.py
+++ b/src/dolores.py
@@ -92,6 +92,24 @@ async def handle_news(message):
                         await ctx.reply(embed=embed)
 
 
+async def handle_question(message):
+    """
+    When someone reacts with a question mark to a message, Dolores will attempt
+    to explain the contents of the message in an informative simpler way.
+    Calls generate_explanation in the generation module.
+    """
+    ctx = await bot.get_context(message)
+
+    if os.environ["GENERATION_ENABLED"].lower() == "true":
+        text_instance = generation(bot)
+        logger.info(f"Generating explanation for message: {message.clean_content}")
+        explanation = text_instance.generate_explanation(
+            message.author.global_name, message.clean_content
+        )
+        if explanation != "":
+            await ctx.reply(explanation)
+
+
 # ---------------------------------------------------------------------------
 # Discord Events
 # ---------------------------------------------------------------------------
@@ -123,6 +141,18 @@ async def on_command_error(ctx, error):
         await ctx.send("An error occurred. Please try again.")
 
 
+@bot.event
+async def on_reaction_add(reaction, user):
+    """
+    on_reaction_add is a base function for handling when a reaction is added
+    to a message. Currently used to check for question mark reaction
+    """
+    if user == bot.user:
+        return
+    if reaction.emoji == "❓" or reaction.emoji == "❔":
+        await handle_question(reaction.message)
+
+
 @bot.event
 async def on_message(message):
     """
diff --git a/src/modules/generation.py b/src/modules/generation.py
index fd20e83..646a1bc 100644
--- a/src/modules/generation.py
+++ b/src/modules/generation.py
@@ -79,6 +79,41 @@ def generate_reply(self, person, message):
 
         return reply
 
+    def generate_explanation(self, person, message):
+        """
+        Generates a simpler more informative explanation to a given message.
+        """
+        # Add the user's message to the message history
+        message_history.append({"role": "user", "content": message, "name": person})
+
+        message_history.append(
+            {
+                "role": "system",
+                "content": "Attempt to explain the previous message if possible. Expand on what they are saying to provide a more informative response. Essentially, explain the contents of the message for somebody else who may not understand what the message is saying.",
+            }
+        )
+
+        try:
+            response = openai.chat.completions.create(
+                model=os.environ["OPENAI_MODEL"],
+                messages=system_messages + list(message_history),
+                max_tokens=int(os.environ.get("MAX_TOKENS", 150)),
+                temperature=float(os.environ.get("TEMPERATURE", 0.9)),
+                top_p=float(os.environ.get("TOP_P", 1.0)),
+                frequency_penalty=float(os.environ.get("FREQUENCY_PENALTY", 0.0)),
+                presence_penalty=float(os.environ.get("PRESENCE_PENALTY", 0.6)),
+            )
+            reply = response.choices[0].message.content
+            logger.info(f"Explanation generated: {reply}")
+            # Add the reply to the message history
+            message_history.append({"role": "assistant", "content": reply})
+        except Exception as e:
+            logger.error(f"Error generating explanation: {e}")
+            logger.error(f"Messages: {system_messages + list(message_history)}")
+            reply = ""
+
+        return reply
+
     def generate_snarky_comment(self):
         """
         Generates a snarky comment to be used when a user tries to use a command that does not exist.
@@ -183,3 +218,6 @@ async def generate_image(self, ctx, *, prompt: str):
         except Exception as e:
             logger.error(e)
             await ctx.respond(f"Error posting image to Discord: {e}.")
+
+    # @commands.slash_command(description="Restates a given message in a more informative way. Explans something.")
+    # async def explainthat(self, ctx)