Finding the Light - When is it too dark to take a portrait photo?

The Holidays are a crazy time of year for everybody. When trying to schedule a photo session you are challenged with finding a day and time that works for you AND your client. Sometimes the weather doesn't cooperate and you have to somehow find a way to find the light and make it work.
This photo shoot was Wednesday, December 5 after school. We met at Binney Park in Old Greenwich after 5pm. The weather was unseasonably warm - a plus - but overcast and therefore VERY dark.
We headed right for one of the beautiful bridges Binney Park is known for at the water's edge. My 42" reflector was a huge help in bouncing some extra light up at the faces. This shot was taken at 5:15pm with an ISO of 4000 in the RAW mode. The magic happened in the post processing phase. I was able to push the exposure substantially to brighten the image. With the high ISO and post processing push the result is a grainy photograph that is a bit moody.

As it got darker, finding the light became more challenging. I took a picture using a flash to see what I could capture. In the picture below you can see just how dark it was at 5:30pm.  The faces are crisp thanks to the bright flash but I feel the result is a flat boring image (despite the gorgeous faces).

Finding the Light - After scanning the park I targeted the lamp posts decorated with strings of lights for the holidays. Using the reflector again I was able to bounce the light back up to the faces to capture some more moody or "artsy" shots.

So when is it too dark to take a portrait using outdoor available light? I would say when you get too tired or hungry.  ;) This adorable elf was our last shot of the evening - dinner time!