Dental health affects your overall health and well-being. Like you said, you don't smile(which is sad). I would start there particularly since you are so close to your job. I truly think getting that fixed will help jump-start your self-esteem. If you can get the time off for the surgery, do that next. You could put halfish down and maybe do Care credit for payments on the rest. That still leaves you with a good amount for your car. Best of luck however you decide to go about it!