Like most others here, I wear a glove until it starts to get a hole in it, usually either on the thumb or pad of my palm. Then I move the glove to my practice bag and wear it until the hole is all the way thru and then it gets tossed out. I tend to practice more than I play, so I usually have a new glove or almost new glove with my playing bag. At the first sign of wearing thru, I'll move the glove to my practice bag. As for hoe long I play a glove, that really depends on the quality of the glove and how well I'm playing. If my hands are slipping on the club due to a bag grip, the glove can wear faster that it should, and that's when I figure it's time to work on my grip and grip pressure. If you gloves wear out pretty fast, it's a good sign that your grip needs work.