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I once had to photograph a two year old with her grandmother. I asked in advance (out of town) if they could have some other person there to assist me. The person ended up being the child's babysitter.
The trouble I had was that the child kept wanting to cling to the babysitter and would not interact with the grandmother. I decided that the babysitter had to go and ask that she leave. After a short while of adjustment the baby settled down with the grandmother.
Also, I think it is more difficult with people that know you well. I would much rather deal with strangers.
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Mike McCarty
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