It is hard to put all the dissociated aspects of our experience into one place, isn't it? I can often feel sad, or have tears, or know what happened, but getting two of them happening at the same time is a bit elusive.
Like you I can more easily feel sadness for another person's experience. If someone is crying near me in person, I will very often well up with tears for them. One thing that is sure to bring me to tears is anything about human beings being decent human beings and truly helping one another. Great acts of empathy and kindness can be like a key to releasing emotion for me, so I often read things like Chicken Soup for the Soul or watch youtube videos about kindness when I need to release pent up and otherwise inexpressible emotions.
I hope you can get yourself a new teddy bear soon.