I doubt it is anything serious, he just doesn't stretch, warm up the muscles/joints a bit by jogging or whatever you want, then stretch, always does you more good when they are warm first, keep on a schedule and your flexiblity will improve.
<< I have long legs, and I can't touch my toes. Whenever I try, the tendons all along the back of my leg get pretty tight, if I keep stretching these (hamstrings?) will I eventually be able to touch my toes? >>
yes, if you keep stretching it will eventually improve your flexibility and you'll be able to do this.
when i was younger and in better shape i could stand flat against a wall and bend down from my waist and touch both palms on the ground next to my feet without bending my knees. it's a great stretching exercise.
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