How do I 'validate' on destroy in rails

You can raise an exception which you then catch. Rails wraps deletes in a transaction, which helps matters.

For example:

class Booking < ActiveRecord::Base
  has_many   :booking_payments
  ....
  def destroy
    raise "Cannot delete booking with payments" unless booking_payments.count == 0
    # ... ok, go ahead and destroy
    super
  end
end

Alternatively you can use the before_destroy callback. This callback is normally used to destroy dependent records, but you can throw an exception or add an error instead.

def before_destroy
  return true if booking_payments.count == 0
  errors.add :base, "Cannot delete booking with payments"
  # or errors.add_to_base in Rails 2
  false
  # Rails 5
  throw(:abort)
end

myBooking.destroy will now return false, and myBooking.errors will be populated on return.

just a note:

For rails 3

class Booking < ActiveRecord::Base

before_destroy :booking_with_payments?

private

def booking_with_payments?
        errors.add(:base, "Cannot delete booking with payments") unless booking_payments.count == 0

        errors.blank? #return false, to not destroy the element, otherwise, it will delete.
end