When should you ask out a service provider?

When you are being serve food or being helped at a store and the person is nice and smile at you. Should you ask her out? You got to understand they people are being paid to be nice to you. That the job!!! But do you think you have a connection? Ask yourself this and be fucking honest. Has women you date in pass are in the same looks range as her or him? If not and you think you may have a chance. She taken. The second question are you willing to not come back to this place? Many questions need to be answer before you will pull the trigger.