which one do you prefer?

Used the 85mm and speedlight on camera for fill.

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definitely #2. background is underexposed slightly, which i prefer. you might back the vignette off a bit so its not so noticeable.

what were your settings? depending on the time of day, you should be able to get at least a little bit of color in that sky and make your subject pop with the speedlight. if you're using on camera I wouldn't drop it down much more than you've got now since it will look very flat, but if you're able to shoot with the light off camera you can get some amazing results.

aaron.dunlap wrote in post #11168137
definitely #2. background is underexposed slightly, which i prefer. you might back the vignette off a bit so its not so noticeable.

what were your settings? depending on the time of day, you should be able to get at least a little bit of color in that sky and make your subject pop with the speedlight. if you're using on camera I wouldn't drop it down much more than you've got now since it will look very flat, but if you're able to shoot with the light off camera you can get some amazing results.

It was late afternoon, grey sky. we were trying to beat the rain so being in such a hurry I used portrait mode. I later learned I should have tried AV mode. I'm thinking I need to learn off camera flash. Thank you for the tips.

#2 is definitely a better balanced edit and composition.

#2 is the best. However, the vignette is too much (as Aaron also posted)

I like them both and don't mind the vignette so much, but the pose needs a little work. Something with his body doing something or more serious or less serious (goofy), but not static the way it is.

#2 with the vignette, just lighten up a bit.

Composition in 2 is better. But the colors on his face are more saturated in a way that makes his flush cheeks look like blush makeup and it almost looks like he's got lipstick. What was done for PP besides vignette?

kraaazymike wrote in post #11172115
Composition in 2 is better. But the colors on his face are more saturated in a way that makes his flush cheeks look like blush makeup and it almost looks like he's got lipstick. What was done for PP besides vignette?

Exactly what he said ^^^^^^^^^^^^^^^
My first thought was, LIPSTICK ALERT!!!
You're composition in #2 is certainly OK - though if it were me, I'd get his head into the top-right sector - but tone down the colour saturation, even if the subject has naturally red lips.