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I hear people say they like to stretch out because it feels good. I've never had that experience. It's not painful, but it's somewhere between unpleasant and neutral. Hence, stretching is work, and I have to struggle to motivate myself to do it.

What are the factors that affect how stretching feels? How can we make it feel good to stretch?

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Stretching to loosen up, or stretching to increase your flexibility? Stretching to loosen up feels good for me unless my muscles hurt from a previous workout. Stretching to increase my flexibility I would never classify as 'feeling good'.

For motivation, pick a time or activity you do often, and always do a short stretch with that. For example, a few years back, I wanted to be able to touch the floor with locked knees. Each time I would use the WC/restroom/toilet/[insert preferred term here] I would do a short amount of stretching (10-20 seconds). It did the trick: after several months, I achieved my goal.

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Ahh... the restroom part is just begging for some trolling, but I believe that that would be frowned upon in this community :) –  Janis Peisenieks Mar 18 '11 at 18:06
    
@JanisPeisenieks: Take it to area51.stackexchange.com/proposals/3303 –  Jay Bazuzi Mar 18 '11 at 18:35
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As I already wrote a lengthy piece about stretching I won't repeat myself too much, but stretching is actually 'meant' to be painful. Your muscle has several proprioceptors (muscle spindles and Golgi tendon organs) that protect the muscle against possible injury. Basically, its supposed to hurt!

While this pain gets less due to habituation of the CNS to the signals of your muscle's nerves, this is more a 'stretch tolerance' than an actual physiological change required to get 'longer' muscles. This only happens when you stretch frequently, which might cause stretch-induced-hyperthrophy. Sadly, this effect is easily lost again if you stop stretching, because your body constantly adapts itself to its loads.

So what can you do?

Exercise with a larger range of motion. Since your body adapts itself to the loads you apply to it, either you should use your body in more stretched positions (with an increased range of motion) or you should forget about stretching altogether, because you won't sustain it anyway.1

An exception to this would be if you have a lack of flexibility due to a wrong posture (Hello programmers!), injury (broken limbs) or some other cause (stroke). In these cases it may be advisable to stretch to retain a more natural posture or range of motion.

1: There may be situations where it is beneficial, however I remain skeptical that these athletes should look at how they exercise before thinking that stretching will solve their problems.

The explanations above are very summarized and somewhat incomplete, for a more complete overview I suggest you read several of the literature reviews about stretching

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