diff --git a/.gitignore b/.gitignore
index db090aa..f21f1b3 100644
--- a/.gitignore
+++ b/.gitignore
@@ -8,4 +8,9 @@
 !app/*
 
 !/app/plugin
-!app/plugin/*
\ No newline at end of file
+!app/plugin/*
+
+app/bot.py
+
+__pycache__/
+.env
\ No newline at end of file
diff --git a/app/config.py b/app/config.py
index 4958e15..29e5ced 100644
--- a/app/config.py
+++ b/app/config.py
@@ -7,8 +7,11 @@ load_dotenv()
 
 
 class config:
-    DATE_START = datetime.strptime(os.environ.get("DATE_START"), "%Y-%m-%d").date()
-    BOT_TOKEN = os.environ.get("API_TOKEN")
+    DATE_START = datetime.strptime(
+        f'{os.environ.get("DATE_START")}-{os.environ.get("TIME_START")}',
+        "%Y-%m-%d-%H:%M",
+    )
+    API_TOKEN = os.environ.get("API_TOKEN")
     ADMIN_ID = os.environ.get("ADMIN_ID")
     ENV = os.getenv("ENV", "PROD")
 
@@ -30,7 +33,11 @@ class Messages:
     WELCOME_LIST = [
         "Привет! Это бот  Quick dates (Random Coffee). Чтобы зарегистрироваться, пожалуйста, ответь на следующие вопросы."  # несколько сообщений подряд
     ]
-    HELP = "Помощь"
+    HELPS = [
+        "Доступные команды:" "\n/start - начать регистрацию" "n/help - помощь",
+        "Начало мероприятия: {} \nЭто через целых {} минут!",
+    ]
+
     ERROR = "Произошла ошибка"
     ENTER_NAME = "Как тебя зовут?"
     ENTER_AGE = "Сколько тебе лет?"
@@ -47,3 +54,6 @@ class Messages:
         \nГруппа: {}\
         \n\nВсё верно?"
     ALREADY_REGISTERED = "Ты уже зарегистрирован. Хочешь изменить данные?"
+    MATCHING_START = (
+        "Мы начали подбор пар. Пожалуйста, подтверди, что ты находишься в аудитории"
+    )
diff --git a/app/db.py b/app/db.py
index 970effd..9ef5c3e 100644
--- a/app/db.py
+++ b/app/db.py
@@ -15,6 +15,9 @@ class DB:
     def find(self, query):
         return self.collection.find(query)
 
+    def find_one(self, query):
+        return self.collection.find_one(query)
+
     def update(self, query, data):
         self.collection.update_one(query, {"$set": data})
 
diff --git a/app/main.py b/app/main.py
index 8181703..07d256d 100644
--- a/app/main.py
+++ b/app/main.py
@@ -8,6 +8,7 @@ from plugin.user import User
 from plugin.admin import Admin, AdminMessages
 from plugin.bot_instance import bot, BotCommands
 from plugin.register import start_reg_name
+from datetime import datetime, timedelta
 import time
 
 
@@ -61,14 +62,11 @@ def start_message(message: types.Message):
 
 @bot.message_handler(commands=BotCommands.Help)
 def help_message(message: types.Message):
-    bot.send_message(
-        message.chat.id,
-        (
-            Messages.HELP
-            if not Admin.is_admin(message.chat.id)
-            else AdminMessages.ADMIN_HELP
-        ),
-    )
+    if not Admin.is_admin(message.chat.id):
+        for msg in Messages.HELPS:
+            bot.send_message(message.chat.id, msg)
+    else:
+        bot.send_message(message.chat.id, AdminMessages.ADMIN_HELP, parse_mode="HTML")
 
     return
 
@@ -76,7 +74,23 @@ def help_message(message: types.Message):
 if __name__ == "__main__":
     print("/t--- Bot started ---")
 
+    time_for_notif = config.DATE_START
+
     while True:
+        if config.DATE_START - datetime.now() < timedelta(days=1):
+            users = User.get_all()
+            for user in users:
+                bot.send_message(
+                    user["user_id"],
+                    "Напоминание, что наше мероприятие пройдёт уже завтра! Следите за новостями)",
+                )
+
+            admins = Admin.get_all_admins()
+            for admin in admins:
+                bot.send_message(
+                    admin["user_id"],
+                    "Отправлено напоминание о скором начале мероприятия.",
+                )
         time.sleep(10)
 
     exit()
diff --git a/app/plugin/admin.py b/app/plugin/admin.py
index 819a429..ebca9a6 100644
--- a/app/plugin/admin.py
+++ b/app/plugin/admin.py
@@ -1,7 +1,10 @@
 from db import DB
 import config
+import os
+import threading
+import time
 from plugin.user import User
-from plugin.shuffle import Shuffle
+from plugin.shuffle import Shuffle, already_matched
 
 from plugin.bot_instance import bot
 
@@ -29,9 +32,13 @@ class Admin:
 
         return
 
+    @staticmethod
+    def get_all_admins():
+        return Admin._db.find({})
+
     @staticmethod
     def is_admin(user_id):
-        return Admin._db.find_one({"user_id": user_id}) is not None
+        return Admin._db.find({"user_id": user_id}) is not None
 
     @staticmethod
     def add_admin(new_user_id, name, unique_key) -> int:
@@ -206,8 +213,6 @@ class Admin:
         with open("admin_stats.txt", "rb") as f:
             bot.send_document(message.chat.id, f)
 
-        import os
-
         os.remove("stats.txt")
         os.remove("admin_stats.txt")
 
@@ -242,7 +247,7 @@ class Admin:
     def clear_all_command(message):
         bot.send_message(
             message.chat.id,
-            "Отправьте <code>delete all</code> для подтверждения",
+            "Отправьте <code>delete all</code> для подтверждения. \n\nВнимание, вы вряд ли хотите это делать.",
             parse_mode="HTML",
         )
 
@@ -263,8 +268,76 @@ class Admin:
     @bot.message_handler(commands=["random"])
     @admin_only
     def random_command(message):
-        users = User.get_all()
-        Shuffle(users)
+        already_matched.clear()
+
+        for admin in Admin.get_all_admins():
+            bot.send_message(
+                admin["user_id"],
+                "Отправлено приглашение пользователем. В данный момент подтвердило участие 0 человек. Запускайте команду /end_random для завершения регистрации",
+            )
+
+        User.start_shuffle_reg()
+
+        def monitor_participation():
+            while True:
+                participants = len(already_matched)
+                bot.send_message(
+                    message.chat.id,
+                    f"В данный момент подтвердило участие {participants} человек",
+                )
+                time.sleep(5)
+
+        thread = threading.Thread(
+            target=monitor_participation, name="monitor_participation"
+        )
+        thread.start()
+
+        return
+
+    @bot.message_handler(commands=["end_random", "random_again"])
+    @admin_only
+    def end_random_command(message):
+        for thread in threading.enumerate():
+            if thread.name == "monitor_participation":
+                thread.kill()
+
+        bot.send_message(message.chat.id, "Регистрация завершена. Ожидайте")
+
+        pairs = Shuffle()
+        for pair in pairs:
+            if pair[1]:
+                bot.send_message(
+                    pair[0].user_id,
+                    f"Ваша пара: {pair[1].name}. Парта находится под номером: {pairs.index(pair) + 1})",
+                )
+                bot.send_message(
+                    pair[1].user_id,
+                    f"Ваша пара: {pair[0].name}. Парта находится под номером: {pairs.index(pair) + 1})",
+                )
+            else:
+                bot.send_message(
+                    pair[0].user_id,
+                    "Подойди к организаторам мероприятия, они тебе подберут идеальную пару!",
+                )
+
+        with open("pairs.txt", "w") as f:
+            str_pair = ""
+            for pair in pairs:
+                str_pair += (
+                    f"Парта {pairs.index(pair) + 1}: {pair[0].name} | {pair[1].name}\n"
+                )
+
+            f.write(str_pair)
+
+        with open("pairs.txt", "rb") as f:
+            for admin in Admin.get_all_admins():
+                bot.send_document(
+                    admin["user_id"],
+                    f,
+                    caption="Распредение по парам.",
+                )
+
+        os.remove("pairs.txt")
 
         return
 
@@ -273,10 +346,11 @@ class AdminMessages:
     ADMIN_HELP = (
         "Вы администратор! Вот что вы можете сделать:\n"
         "/remove_admin - удалить админа\n"
-        "/generate_key - сгенерировать уникальный ключ"
-        "/delete_user - удалить пользователя"
-        "/stats - статистика"
-        "/send_message - отправить всем сообщение"
-        "/random - зарандомить людей для 1 тура"
-        "clear_all - удаляет ВСЕХ пользователей"
+        "/generate_key - сгенерировать уникальный ключ\n"
+        "/delete_user - удалить пользователя\n"
+        "/stats - статистика\n"
+        "/send_message - отправить всем сообщение\n"
+        "/random - зарандомить людей для 1 тура\n"
+        "/random_again - зарандомить людей без повторной регистрации\n"
+        "<code>clear_all</code> - удаляет ВСЕХ пользователей для их повторной регистрации\n"
     )
diff --git a/app/plugin/bot_instance.py b/app/plugin/bot_instance.py
index 6f77a77..5e12998 100644
--- a/app/plugin/bot_instance.py
+++ b/app/plugin/bot_instance.py
@@ -1,5 +1,5 @@
 import telebot
-import config
+from config import config
 import threading
 
 
@@ -9,7 +9,7 @@ class BotCommands:
 
 
 bot = telebot.TeleBot(
-    config.BOT_TOKEN,
+    config.API_TOKEN,
     colorful_logs=True,
 )
 
diff --git a/app/plugin/register.py b/app/plugin/register.py
index 55d7426..404c1d3 100644
--- a/app/plugin/register.py
+++ b/app/plugin/register.py
@@ -4,6 +4,8 @@ from config import Messages
 from plugin.test import TestMessages
 
 from plugin.bot_instance import bot
+import os
+import re
 
 
 def start_reg_name(message: types.Message):
@@ -159,11 +161,24 @@ def show_result(message: types.Message):
         TestMessages.TEST_RESULTS[user.type][0],
         TestMessages.TEST_RESULTS[user.type][1],
     )
-    bot.send_photo(
-        message.chat.id,
-        open(f"pics/{user.type}.jpg", "rb"),
-        caption=text,
-    )
+
+    directory = "pics/"
+    pattern = re.compile(f"{user.type}.*\.(jpg|jpeg|png|gif)$", re.IGNORECASE)
+
+    image_path = None
+    for filename in os.listdir(directory):
+        if pattern.match(filename):
+            image_path = os.path.join(directory, filename)
+            break
+
+    if image_path:
+        bot.send_photo(
+            message.chat.id,
+            open(image_path, "rb"),
+            caption=text,
+        )
+    else:
+        print("Image not found")
 
     bot.send_message(message.chat.id, TestMessages.TEST_FINISH)
 
diff --git a/app/plugin/shuffle.py b/app/plugin/shuffle.py
index 514b7fc..ced1092 100644
--- a/app/plugin/shuffle.py
+++ b/app/plugin/shuffle.py
@@ -1,6 +1,155 @@
-from plugin.user import User
+from plugin.user import User, users_reg
+from typing import List, Tuple
+import random
+
+already_matched: List[Tuple[User, User]] = []
 
 
-def Shuffle(users: list[User]):
+def Shuffle() -> List[Tuple[User, User]]:
+    users = users_reg.copy()
+    random.shuffle(users)
+    pairs = []
 
-    return
+    if len(users) % 2 != 0:
+        pairs.append((users.pop(),))
+
+    # Step 1: Match men with women by compatibility and age
+    for user in users:
+        for potential_match in users:
+            if user == potential_match:
+                continue
+            if (
+                user.gender != potential_match.gender
+                and potential_match.type in compatibility[user.type]
+                and abs(user.age - potential_match.age) <= 5
+                and (user, potential_match) not in already_matched
+                and (potential_match, user) not in already_matched
+            ):
+                pairs.append((user, potential_match))
+                users.remove(user)
+                users.remove(potential_match)
+                break
+
+    # Step 2: Match men with women with compatibility
+    for user in users:
+        for potential_match in users:
+            if user == potential_match:
+                continue
+            if (
+                user.gender != potential_match.gender
+                and potential_match.type in compatibility[user.type]
+                and (user, potential_match) not in already_matched
+                and (potential_match, user) not in already_matched
+            ):
+                pairs.append((user, potential_match))
+                users.remove(user)
+                users.remove(potential_match)
+                break
+
+    # Step 3: Match men with women
+    for user in users:
+        for potential_match in users:
+            if user == potential_match:
+                continue
+            if (
+                user.gender != potential_match.gender
+                and (user, potential_match) not in already_matched
+                and (potential_match, user) not in already_matched
+            ):
+                pairs.append((user, potential_match))
+                users.remove(user)
+                users.remove(potential_match)
+                break
+
+    # Step 4: Match people of the same age
+    for user in users:
+        for potential_match in users:
+            if user == potential_match:
+                continue
+            if (
+                user.age == potential_match.age
+                and (user, potential_match) not in already_matched
+                and (potential_match, user) not in already_matched
+            ):
+                pairs.append((user, potential_match))
+                users.remove(user)
+                users.remove(potential_match)
+                break
+
+    # Step 5: Pair all remaining users
+    while len(users) > 1:
+        pairs.append((users.pop(), users.pop()))
+
+    already_matched.extend(pairs)
+
+    return pairs
+
+
+compatibility = {
+    "INTJ": (
+        "ENFP",
+        "ENTP",
+    ),
+    "INTP": (
+        "ENTJ",
+        "ESTJ",
+    ),
+    "INFJ": (
+        "ENFP",
+        "ENTP",
+    ),
+    "INFP": (
+        "ENFJ",
+        "ENTJ",
+    ),
+    "ISTJ": (
+        "ESFP",
+        "ESTP",
+    ),
+    "ISTP": (
+        "ESFJ",
+        "ESTJ",
+    ),
+    "ISFJ": (
+        "ESFP",
+        "ESTP",
+    ),
+    "ISFP": (
+        "ENFJ",
+        "ESFJ",
+        "ESTJ",
+    ),
+    "ENTJ": (
+        "INFP",
+        "INTP",
+    ),
+    "ENTP": (
+        "INTJ",
+        "ENTP",
+    ),
+    "ENFJ": (
+        "INFP",
+        "ISFP",
+        "ENFJ",
+    ),
+    "ENFP": (
+        "INFJ",
+        "INTJ",
+    ),
+    "ESTJ": (
+        "ISFP",
+        "ISTP",
+    ),
+    "ESTP": (
+        "ISFJ",
+        "ISTJ",
+    ),
+    "ESFJ": (
+        "ISFP",
+        "ISTP",
+    ),
+    "ESFP": (
+        "ISTJ",
+        "ISFJ",
+    ),
+}
diff --git a/app/plugin/user.py b/app/plugin/user.py
index 110faae..e126433 100644
--- a/app/plugin/user.py
+++ b/app/plugin/user.py
@@ -1,4 +1,10 @@
 from db import DB
+from plugin.bot_instance import bot
+from config import Messages
+from telebot import types
+from typing import List, Tuple
+
+users_reg: List["User"] = []
 
 
 class User:
@@ -119,12 +125,42 @@ class User:
 
         data = self._db.find_one({"_id": self.user_id})
         self._name = data["name"]
+
         self._age = data["age"]
         self._gender = data["gender"]
         self._faculty = data["faculty"]
         self._group = data["group"]
         self._type = data["type"]
 
+    @staticmethod
+    def start_shuffle_reg():
+        users_reg.clear()
+        users = [user for user in User.get_all() if user.type]
+
+        markup = types.InlineKeyboardMarkup()
+        markup.add(
+            types.InlineKeyboardButton("Я тут!", callback_data="shuffle_agree"),
+        )
+
+        for user in users:
+            bot.send_message(user.user_id, Messages.MATCHING_START, reply_markup=markup)
+
+        @bot.callback_query_handler(func=lambda call: call.data == "shuffle_agree")
+        def add_user_to_reg(call: types.CallbackQuery):
+            user = User(call.message.chat.id)
+            users_reg.append(user)
+
+            bot.edit_message_text(
+                call.message.chat.id,
+                call.message.message_id,
+                "Вы добавлены в список участников! Пожалуйста, подождите, пока все зарегистрируются",
+                reply_markup=None,
+            )
+
+            return
+
+        return
+
     def __str__(self):
         text = [f"{var}: {vars(self)[var]}" for var in vars(self) if var]
         text = "\n".join(text)
diff --git a/requirements.txt b/app/requirements.txt
similarity index 100%
rename from requirements.txt
rename to app/requirements.txt
diff --git a/docker-compose.yaml b/docker-compose.yaml
index 9db6ff3..6afeefa 100644
--- a/docker-compose.yaml
+++ b/docker-compose.yaml
@@ -6,12 +6,12 @@ services:
     container_name: python_bot
     working_dir: /usr/src/app
     volumes:
-      - .:/usr/src/app
+      - ./app:/usr/src/app
     networks:
       - rc_network
     depends_on:
       - mongodb
-    command: sh -c "pip install -r requirements.txt && python bot.py"
+    command: sh -c "pip install -r requirements.txt && python main.py"
 
   mongodb:
     image: mongo:latest