I sprained my ankle 10-20 times already. it's painful. i've worn a ankle boot for 6 months. it stopped hurting but it came back? what should i do now?

Be seen: You would be wise to be seen and evaluated. When someone "sprains" there ankle, they stretch or tear ligaments that stabilize the ankle. They will often heal and so most people who sprain there ankle fully recover. But sometimes the ligaments don't heal and chronic instability with recurrent sprains can result. Ligament reconstruction may be indicated.