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Outdoor Photography in the Evening how to make my pictures turn out?

I will be taking prom pictures again this year for some high school students. Typically this happens in the evening so the lighting to me is difficult to work with. I did a shoot with some kids last year and their pictures turned out pretty well. Wondering what I could do or get for my camera that helps with the quality of the pictures. I am relatively new to taking pictures. I have a Canon Rebel T5. I will be working against the clock again this year to preserve that valuable lighting. How can I extend my picture taking time. Do I need a speedlight? a diffuser? should i be using flash? when i did it turned out too bright. any advice would be greatly appreciated. The lighting was hard to work with on this picture, turned out dark and had trouble editingThis picture turned out decent in my opinion in terms of lighting