First thing is to forget the dry weights. Use the trailer GVWR from the tag on the left front of the trailer. This is the maximum weight of the loaded trailer. To estimate your loaded pin weight take 20 to 22% of the trailer GVWR.
Now look on the drivers door jamb for a yellow sticker that provides the payload capacity of the truck. Take your estimated pin weight plus a hitch plus passengers plus any cargo in the truck bed. All of that added up needs to be less then the payload capacity of the truck.
A 1/2 ton truck will reach its payload capacity long before you reach the trucks maximum towing capacity.
Good luck.
Ken