questionswhat canon lens/flash/strobe should i get next?

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your nifty fifty should be great for portraiture, but if you need to get a little closer - the 85mm f1.8 prime is an excellent lens, that won't make things too soft. They aren't cheap but you can find them used for around 200 and on sale (sometimes) for 350+.

For lighting - obviously try to control the lighting as much as you can without flashing, but if you must - stick to side lighting with a UV trigger. I like bower and vivitar flashes - they tend to be cheaper than canon speedlights, but are as good or better for the money.

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I'm completely a newbie to the DSLR world but so far everything I've read said the nifty fifty is ideal for portraits. With my kit lens, a telephoto and the 50 on order, I hope I'll be good for a while.