diff --git a/BotSecrets.json.template b/BotSecrets.json.template
index b5c2766..c676f43 100644
--- a/BotSecrets.json.template
+++ b/BotSecrets.json.template
@@ -9,6 +9,7 @@
     "WeatherKey": "",
     "GeocodeKey": "",
     "AzureTranslateKey": "",
+    "ApiNinjasKey" : "",
     "ClassArchiveCategoryIds": [],
     "ClassNotifsChannelId": ""
 }
diff --git a/bot/bot_secrets.py b/bot/bot_secrets.py
index 4f3f395..766aa63 100644
--- a/bot/bot_secrets.py
+++ b/bot/bot_secrets.py
@@ -17,6 +17,7 @@ def __init__(self) -> None:
         self._weather_key: str | None = None
         self._geocode_key: str | None = None
         self._azure_translate_key: str | None = None
+        self._api_ninjas_key: str | None = None
         self._startup_log_channel_ids: list[int] | None = None
         self._error_log_channel_ids: list[int] | None = None
         self._class_archive_category_ids: list[int] | None = None
@@ -151,6 +152,18 @@ def azure_translate_key(self, value: str | None) -> None:
             raise ConfigAccessError("azure_translate_key has already been initialized")
         self._azure_translate_key = value
 
+    @property
+    def api_ninjas_key(self) -> str:
+        if not self._api_ninjas_key:
+            raise ConfigAccessError("api_ninjas_key has not been initialized")
+        return self._api_ninjas_key
+
+    @api_ninjas_key.setter
+    def api_ninjas_key(self, value: str | None) -> None:
+        if self._api_ninjas_key:
+            raise ConfigAccessError("api_ninjas_key has already been initialized")
+        self._api_ninjas_key = value
+
     @property
     def class_archive_category_ids(self) -> list[int]:
         if not self._class_archive_category_ids:
@@ -188,6 +201,7 @@ def load_development_secrets(self, lines: str) -> None:
         self.weather_key = secrets["WeatherKey"]
         self.geocode_key = secrets["GeocodeKey"]
         self.azure_translate_key = secrets["AzureTranslateKey"]
+        self.api_ninjas_key = secrets["ApiNinjasKey"]
         self.class_archive_category_ids = secrets["ClassArchiveCategoryIds"]
         self.class_notifs_channel_id = secrets["ClassNotifsChannelId"]
 
@@ -210,6 +224,7 @@ def load_production_secrets(self) -> None:
         self.weather_key = os.environ.get("WEATHER_KEY")  # type: ignore
         self.geocode_key = os.environ.get("GEOCODE_KEY")  # type: ignore
         self.azure_translate_key = os.environ.get("AZURE_TRANSLATE_KEY")  # type: ignore
+        self.api_ninjas_key = os.environ.get("API_NINJAS_KEY")  # type: ignore
         self.class_archive_category_ids = [
             int(n) for n in os.environ.get("CLASS_ARCHIVE_CATEGORY_IDS").split(",")  # type: ignore
         ]
diff --git a/bot/cogs/dad_joke_cog.py b/bot/cogs/dad_joke_cog.py
new file mode 100644
index 0000000..c7a7a8d
--- /dev/null
+++ b/bot/cogs/dad_joke_cog.py
@@ -0,0 +1,97 @@
+import logging
+import random
+
+import aiohttp
+import discord
+import discord.ext.commands as commands
+
+import bot.extensions as ext
+from bot.consts import Colors
+
+log = logging.getLogger(__name__)
+DAD_JOKE_URL = 'https://icanhazdadjoke.com/'
+
+REQ_HEADERS = {
+    'User-Agent': 'SockBot (https://github.com/Jay-Madden/SockBot)',
+    'Accept' : 'application/json'
+}
+
+class DadJokeCog(commands.Cog):
+
+    def __init__(self, bot):
+        self.bot = bot
+    
+    ##########################
+    # USER EXECUTABLE COMMANDS    
+    # Random Dad Joke
+    @ext.group(case_insensitive=True, invoke_without_command=True, aliases=['dad', 'dj'])
+    @ext.long_help(
+        """
+        This command provides a random dad joke.
+        """
+    )
+    @ext.short_help('Get a Dad Joke!')
+    @ext.example(('dadjoke', 'dad', 'dj'))
+    async def dadjoke(self, ctx):
+        try:
+            async with aiohttp.request("GET", DAD_JOKE_URL, headers=REQ_HEADERS) as response:
+                if (response.status != 200):
+                    embed = discord.Embed(title='SockDad', color=Colors.Error)
+                    ErrMsg = f'Error Code: {response.status}'
+                    embed.add_field(name='Error with the dad joke API', value=ErrMsg, inline=False)
+                    await ctx.send(embed=embed)
+                    return
+                joke_json = await response.json()
+        except Exception as err:
+            raise Exception(err).with_traceback(err.__traceback__)
+        
+        embed = discord.Embed(title='SockDad', color=Colors.Purple)
+        embed.add_field(name='Joke:', value=joke_json.get("joke", ""), inline=False)
+        await ctx.send(embed=embed)
+        return
+    
+    # Dad joke with a focus term.
+    @dadjoke.command()
+    @ext.long_help(
+        """
+        This command provides a dad joke for a given term.
+        
+        Sometimes a Dad needs some direction.
+        """
+    )
+    @ext.short_help('Get a special Dad Joke!')
+    @ext.example(('dadjoke focus <term>', 'dad focus hipster', 'dj focus dog'))
+    async def focus(self, ctx, term):
+
+        req_params = {
+            'term': term,
+            'limit': 30
+        }
+
+        try:
+            async with aiohttp.request("GET", DAD_JOKE_URL + 'search', headers=REQ_HEADERS, params=req_params) as response:
+                if (response.status != 200):
+                    embed = discord.Embed(title='SockDad', color=Colors.Error)
+                    ErrMsg = f'Error Code: {response.status}'
+                    embed.add_field(name='Error with the dad joke API', value=ErrMsg, inline=False)
+                    await ctx.send(embed=embed)
+                    return
+                joke_json = await response.json()
+        except Exception as err:
+            raise Exception(err).with_traceback(err.__traceback__)
+        
+        joke = joke_json.get("results", [])
+
+        if len(joke) > 0:
+            joke = random.choice(joke).get("joke", "")
+        else:
+            joke = 'No results for that term. :\'('
+
+        embed = discord.Embed(title='SockDad', color=Colors.Purple)
+        embed.add_field(name='Joke:', value=joke, inline=False)
+        await ctx.send(embed=embed)
+        return
+
+
+async def setup(bot):
+    await bot.add_cog(DadJokeCog(bot))
\ No newline at end of file
diff --git a/bot/cogs/riddle_cog.py b/bot/cogs/riddle_cog.py
new file mode 100644
index 0000000..aac4af7
--- /dev/null
+++ b/bot/cogs/riddle_cog.py
@@ -0,0 +1,121 @@
+import logging
+import random
+
+import aiohttp
+import discord
+import discord.ext.commands as commands
+
+import bot.extensions as ext
+import bot.bot_secrets as bot_secrets
+from bot.consts import Colors
+
+log = logging.getLogger(__name__)
+RIDDLES_API_URL = 'https://api.api-ninjas.com/v1/riddles'
+
+EMOJI_MAP = {
+    '🇦': 0,
+    '🇧': 1,
+    '🇨': 2,
+    '🇩': 3
+}
+REV_EMOJI_MAP = {
+    0: '🇦',
+    1: '🇧',
+    2: '🇨',
+    3: '🇩'
+}
+
+class RiddleCog(commands.Cog):
+
+    def __init__(self, bot):
+        self.bot = bot
+
+    
+    ##########################
+    # USER EXECUTABLE COMMANDS    
+    # Guess the riddle
+    @ext.group(case_insensitive=True, invoke_without_command=True, aliases=['riddler'])
+    @ext.long_help(
+        """
+        This command allows you to play a riddle guessing game.
+
+        Choose between 4 answers to guess the riddle's answer.
+        """
+    )
+    @ext.short_help('Guess a riddle!')
+    @ext.example(('riddle', 'riddler'))
+    async def riddle(self, ctx):
+        self.api_ninjas_key = bot_secrets.secrets.api_ninjas_key
+
+        headers = {
+            'X-Api-Key': self.api_ninjas_key
+        }
+
+        params = {
+            'limit': 4
+        }
+        
+        try:
+            async with aiohttp.request("GET", RIDDLES_API_URL, headers=headers, params=params) as response:
+                if (response.status != 200):
+                    embed = discord.Embed(title='The Riddler (in Socks)', color=Colors.Error)
+                    ErrMsg = f'Error Code: {response.status}'
+                    embed.add_field(name='Error with the riddle API', value=ErrMsg, inline=False)
+                    await ctx.send(embed=embed)
+                    return
+                riddle_list = await response.json()
+        except Exception as err:
+            raise Exception(err).with_traceback(err.__traceback__)
+        
+        correct_riddle = riddle_list[0]
+
+        # Keep track of original index since 0 is correct
+        answers = [
+            {
+                "answer": riddle.get("answer", "default answer"),
+                "index": index
+            } 
+            for index, riddle in enumerate(riddle_list)
+            ]
+        random.shuffle(answers)
+
+        options_text = ""
+        for index, answer in enumerate(answers):
+            options_text += f"{REV_EMOJI_MAP[index]} : {answer.get('answer', '')}\n\n"
+
+        embed = discord.Embed(title='The Riddler (in Socks)', color=Colors.Purple)
+        embed.add_field(name=correct_riddle.get("title", "Riddle:"), value=correct_riddle.get("question", "No question. :\'("), inline=False)
+        embed.add_field(name="Options:", value=options_text, inline=False)
+        message = await ctx.send(embed=embed)
+
+        for key in EMOJI_MAP.keys():
+            await message.add_reaction(key)
+
+        reaction, _ = await self.bot.wait_for(
+            "reaction_add",
+            check=lambda r, u: r.message.id == message.id
+            and ctx.author.id == u.id,
+            timeout=None,
+        )
+
+        await message.delete()
+
+        # This means it is correct
+        if answers[EMOJI_MAP[reaction.emoji]].get("index") == 0:
+            embed = discord.Embed(title='Correct!', color=0x008000)
+            embed.add_field(name=correct_riddle.get("title", "Riddle:"), value=correct_riddle.get("question", "No question. :\'("), inline=False)
+            embed.add_field(name="Correct Answer:", value=correct_riddle.get("answer", "default answer"), inline=False)
+            embed.add_field(name="Your Answer:", value=answers[EMOJI_MAP[reaction.emoji]].get("answer", "default answer"), inline=False)
+            await ctx.send(embed=embed)
+        # Incorrect
+        else:
+            embed = discord.Embed(title='Wrong!', color=Colors.Error)
+            embed.add_field(name=correct_riddle.get("title", "Riddle:"), value=correct_riddle.get("question", "No question. :\'("), inline=False)
+            embed.add_field(name="Correct Answer:", value=correct_riddle.get("answer", "default answer"), inline=False)
+            embed.add_field(name="Your Answer:", value=answers[EMOJI_MAP[reaction.emoji]].get("answer", "default answer"), inline=False)
+            await ctx.send(embed=embed)
+
+        return
+
+async def setup(bot):
+    await bot.add_cog(RiddleCog(bot))
\ No newline at end of file