Portraits for online dating

A 50 on a crop should be ok. Post processing should be minimal in my opinion, just get the skin tones right.

I'd be more focused on lighting and pose than anything else personally.
 
How will a 17-85mm canon do?

Will be fine, set it somewhere over 50mm and be carefull with your back ground, lighting and posing are the key things to focus on here. Personally I'd look for some good natural lighting as it's nearly always more flatering and normal looking then just make sure your relaxed and well presented take lots of shots and pick the best few. PP should be minimal to none, slight white balance/colouration tweak but the camera will probably get it close enough.
 
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