Very interesting/confusing ideas all. Here's my two cents:
Maybe the shadow is kinda like the Ranger part of him that davem was talking about. It was a side that I think Aragorn himself wasn't too fond of, so he would call it a shadow.
And what do you think of in a Ranger: a dark stranger hidden in the corner, shadows drawn about him... The "bad boy", the "rebel". Gals always fall to some extent for the bad boys, like Han Solo (a scruffy-looking nerf-herder), Indy, Bond, Peter Pan (rebel against parents and maturity), Robin Hood (Prince of Thieves).
I think you're on the right track, davem, about why Wormtongue liked Éowyn, because of her shadow. A deep shadow of loneliness and despair, which he thought only he understood and could give comfort for. And of course she was gorgeous.....
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