Find childhood photographs of someone important to you holding a treasured teddy bear. Bring it to a tattoo artist and build a design around it. You can add a more personal meaning by including a tattoo of a teddy bear or stuffed animal you played with as a child in the design.
Blend the cute and cuddly with the dark and dramatic. One side of the teddy bear's body is the usual furry bundle of love--the other side is skull and bones. The implication doesn't need to be cynical or ugly; you could be making a statement about how "real" your teddy bear seemed to you as a kid.
Find a photograph of a real bear cuddling a cub. Have your tattoo artist substitute the cub for a teddy bear. The design merges your sentimental attachment to a childhood teddy bear with your adult reverence for real bears.