Just starting to do some portrait work

Use a tripod, make sure your shutter speed is fast enough or your friend keeps still. If you use a window, try to have a white surface as a reflector to fill in the shadows a little. Do more than less shots and then make your selection.

Have fun while doing it.

I would do a practice shoot long before the actual event. Borrow a neighbor, wife or one of your kids and do a shoot under similar conditions so you'll get an idea what issues you will face. It's next to impossible for to predict ahead of time the issues/problems you will encounter except to say you *will* encounter problems. Best to have an idea of the problems before hand instead of during a shoot.

Good luck!

If your lens has VR, make sure to turn it off when the camera is on the tripod

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A blank wall or backdrop makes an image...