Cloudy and fill flash

Another cloudy day.

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You say "Another cloudy day" like it's a bad thing. Cloudy days are wonderful for shooting portraits anytime during the day, even at high noon. The clouds act like a giant softbox and while they do produce images with flat lighting and void of catch lights, you can add a little of your own light to produce shadows and catch lights.

The pose in the first image seems to have him in somewhat of an awkward position. I hope you don't mind, but I edited and cropped it differently to show you an alternative. I also reduced the flash on his face a little since it seems just a little bright to me. Also, for future shots, you may suggest that he relax his chin. If you want, I'll delete my edit.

Don't mind the edit at all, thanks.

I said "another cloudy day" because I have a previous post with a cloudy day. I meant it as one more. I love cloudy days for portraits. I agree with you 100% about it.

On a cloudy day, think of the ambient light as the Fill source, so get your ETTL flash OFF the camera to the side a bit where it serves as a Main source and is brighter than the ambient by about +1EV. It will make for much more flattering photos, rather than the bright highlight smack in the center of the face/forehead where it provides zero benefit in modelling facial features.