Should i get this checked out? Wrist problem?

Repetitive movement like pulling pints could cause carpel tunnel syndrome. You really do need to see a doctor. There are things you can wear on your wrist to prevent this getting any worse. Factory workers also tend to get this. It is caused by useing the same motion over and over. It can be very painfull and if not prevented can go to the elbow and then the shoulder of the effected arm.