containers.rb

module TestContainer
  extend Discordrb::EventContainer

  message contains: /i'm (.+)/ do |event|
    event.respond("Hi, #{event.content.match(/i'm (.+)\b/)[1]}. I'm Dad!")
  end
end

module CommandContainer
  extend Discordrb::Commands::CommandContainer

  command :ping do |event|
    'Pong!'
  end

  command :'8ball' do |event|
    ['yes', 'no', 'maybe', 'unsure', 'ask again later', 'unlikely'].sample
  end
end

main.rb

require 'discordrb'

load 'containers.rb'

CONTAINERS = [TestContainer, CommandContainer]

def load_containers(bot)
  # Remove all handlers
  bot.clear!
  CONTAINERS.map(&:clear!)

  # Reload the file
  load 'containers.rb'

  # Register handlers onto the bot
  CONTAINERS.each do |container|
    Discordrb::LOGGER.info("Loading #{container.name}")
    container.clear!
    bot.include!(container)
  end
end

bot = Discordrb::Commands::CommandBot.new(token: ENV['INOSUKE_TOKEN'], prefix: '.')

# Load initial containers
CONTAINERS.each {|container| bot.include!(container) }

bot.command(:reload) do |event|
    load_containers(event.bot)
end

bot.run