Re: For all the health nuts and athletes...
Not a health nut but was a competitive distance runner for many years. In my experience, you should not stretch to the point it is painful. Stretch until you feel a slight pull, do not bounce with the stretch, just hold it steady for x number of seconds.
The more you stretch, over time, the more limber you will become. The further you will be able to extend before felling the pulling sensation. Do not go beyond that point though. It may feel uncomfortable for a while, but that will subside as you become more limber.