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Two plants combined how is best to prune

NeganNegan Posts: 30
I have 2 plants which are intertwined and about 10 foot high. One is a rose not sure on other. I was thinking of trimming rose down to about 4 or 5 foot. Can you inform best time to prune both plants and how drastic I should be on the pruning. Below is a combined picture and close of of second tree/shrub to help identify 


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