Stuff about Stretching
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It sounds silly, but it's best to warm up before stretching. When you warm up, you get blood circulating through your body (and your muscles) and your muscles will stretch easier. Good warm-ups include slow exercise of larger muscle groups... something like walking, riding a bike, or those cool elliptical machines found in most gyms. Warm-up for 5-10 minutes (at a low intensity) and then get ready to stretch.
How to Stretch
If you haven't been stretching regularly, don't expect to contort your body into amazing yoga positions. Use slow, gradual stretching to elongate the muscle to the furthest comfortable position. Don't follow the "No Pain, No Gain" motto when it comes to stretching. Stretch as far as you can without pain, and hold on for 15-30 seconds. This may seem like eternity if you're just starting, but hang in there... it gets easier... and you'll feel better overall as you become more flexible.
When to Stretch
At a minimum, you should stretch before and after exercise. Stretching beforehand, reduces your chances of injury, and improves flexibility for your work-out or activity. You'll make the most flexibility gains after exercise because your body temperature is up and your muscles are warm. Even if you don't care about winning any flexibility awards, stretching afterwards helps with muscle relaxation, facilitates removal of lactic acid (the stuff that makes your muscle start to burn when you're really pumping iron), and increases circulation to joints and tissues.
If you're working a particular body part, it's a good idea to frequently stretch that muscle throughout your work-out as well. Not only will it keep your muscles loose during your work-out, but it will help you achieve maximum range of motion, and reduce muscle soreness later on.
Most people don't work out on a daily basis, but if you can be disciplined enough to stretch each muscle group... everyday... then HOORAY for you. You'll reap the benefits!
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