How do you handle photos like this?
There was a six-stop difference between the light on Matt and that in the window behind him. I exposed for Matt. What are other ways to deal with this sort of situation? Expose for the window to get silhouettes? Hope that Matt stays very, very still and get a two-exposure HDR image? I'm a complete novice when it comes to my understanding of lighting, so any tips are appreciated. Thanks!
I have no idea what you should do before shooting this picture, but this is how I would do to save it after I shot it!... I am not sure how you see it at your end since I am out of town and was playing with it on my laptop, which is not the best way for PP!
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You could also try one of the following:
shoot a copy of the background with no subject at an appropriate exposure, and use it to fix the shot by compositing in photoshop,
shoot in RAW & export 3 images at -3, 0, +3 EV (or similar) & use a HDR program to combine these & perhaps get a good result (by tonemapping the HDR). Some RAW converters will do this same thing to a degree without exporting (HDR style editing)
expose for the background and use a flash to fill the subject.
Just a thought, but you have probably metered off the dark shirt which is why the background is over exposed.
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