So I've been shooting with the kit lens on my 90D for about a year now and I finally feel like I'm hitting a wall with it. Specifically for portraits. I've got my sisters engagement shoot coming up in late September and then her actual wedding in October-just doing some casual shots for that, not the main pro-and I really want that creamy, blurry background look that my 18-135mm just isnt giving me.

I spent the last few days googling and reading every thread on DPReview and Reddit I could find. Everyone keeps saying the 50mm f/1.8 STM is a must have because it's cheap and sharp but then I see other people swearing by the 85mm f/1.8 USM for the compression and better bokeh. This is where I'm getting stuck. Since the 90D has that 1.6x crop factor, that 50mm is actually acting like an 80mm and the 85mm is more like a 136mm lens.

I did some test shots with my zoom lens set at those focal lengths and I'm worried the 85mm is gonna be way too tight if we end up doing any shots indoors or in her small backyard in Jersey City. But then I read that the 50mm can sometimes distort faces if you get too close for headshots. My budget is probably around $500 or $600 max so I could maybe even look at a Sigma Art lens if I find a good deal used but I'm just so torn on which focal length is actually the sweet spot for a crop sensor like mine. I want something that makes people look good without me having to stand three blocks away just to fit their shoulders in the frame.

Should I just stick with the classic 50mm or is the 85mm worth the extra hassle of moving around? Or is there some other lens I'm totally missing that works better for the 90D...