This is incredibly helpful!  You're a superstar!

Excellent, very helpful. Thanks for putting this together. 

I am having some problems with stretching, I never stretched much as a kid, but I already know that just makes it that much harder to get flexible.  But after stretching for three months, I have barely got any more flexible.  So since it is hard for me to get flexible in the first place, should I be stretching twice as hard to get flexible, or what? Like should I do deeper stretching, so that I trully feel a good stretch?

Sorry, gear, for taking so long to respond to this. I think my cookies were goofy on my computer or something. Thank you very much for the feedback. It means a lot. Feel free to add/delete/modify whatever as you see fit. I appreciate your willingness to do so. Happy to help out any way I can.

Go for it. If you want good/best results for flexibility, you need to stretch 3-5x a day. Mostly obviously when you're not working out.

Also, it's mainly passive or excessive amounts of dynamic stretching that shouldn't be done before workouts. Doing some dynamic like leg swings, rotating the arms.. really anything to warm up the muscles without jerking them to their range of motion or holding them stretched will work.

Very helpful, both of you.

Yes and no. The thing is, your muscles are more supple when they are warm and therefore you get the most benefit out of stretching warm (no matter which kind of stretching you do). Also, you are more prone to injury when stretching cold. Being more prone to injury does not guarantee that you will get injured; as a result I know plenty of people (myself included) who static passive stretch cold and do just fine. It's a matter of knowing your limits and knowing how to feel and understand your body. Typically I get a better stretch when I'm warm, though, so to me it makes more sense to stretch warm. Why do a thing if it's not going to be done as close to the ideal as possible?

Since most people don't know how to stretch properly, I'm giving advice on ideal conditions for stretching as a starting point.

You say that you "don't see cold stretching affecting anyone." I assume you're speaking from experience here--as some kind of trainer or coach? It sounds like you observe people cold stretching a lot and have information to add. If that's the case, awesome! I'm always looking to expand my knowledge--especially since I'm not officially a personal trainer or anything like that. I'm just someone with a lot of personal experience with movement and flexibility training in a general sense. So if you have other evidence to support cold stretching, let me know. I'd be interested in reading up on it.

It depends on one of two things:

1. your level of flexibility
2. your technique

It could be a combination of both. It depends a lot on what you mean by "painful." Is it a sharp sudden pain? Dull pain? A general "uncomfortableness" in the muscles? Tightness? Or is the pain more in the joints? Does the pain go away as you sit in the stretch, or does it get worse? If you are incorrectly holding a position you may feel pain in certain areas as things get yanked on. If you are simply inflexible you may be pushing too hard.

The key is to relax, and to stretch daily, with proper alignment.

Most people feel that "something is happening" in the muscles they're stretching, and it may be a bit uncomfortable, but after a few seconds it should be pleasant. I tend to feel very refreshed after a full stretching session, and in fact feel out-of-sorts if I can't get a good stretch in before or after a ballet class. At the COPK jam I led a handful of guys through a general stretching session at the end of the day. Most of these were guys who didn't stretch regularly and they were a bit uncomfortable for a while but afterwards they said they felt really good, and they all noticed a difference the next day: they were among the few who weren't sore for the next day's jammage!