Guy with a bike

I'm looking for some suggestions.
Recently, my coworker asked me if I could take a couple pictures of him. I'm always on a lookout for new opportunities, especially with a willing model, so I've agreed.
This time, I want to approach it differently and use my knowledge to get a good portrait of him.

Here's what I want to capture:
Since he often rides his bicycle to work, looking a bit grungy, more like a rogue city messenger, rather than an office rat, I wanted to capture that side of his. I want to photograph him with city landscape as a background, preferably about 30 minutes after the sunset to get some of the deep blue sky, but still have some ambient light.
I'd like to light his left side with a softbox to cover his face and the body just below the waist and have either a reflector or another light on the other side to light the handlebars of the bike.
There are a few tall office buildings I can use as a background, which could be nice, because of repetitive pattern.
I want to keep the camera a tad lower than his chin to reflect his height - he's a tall fella.
Any suggestions to this setup?

Thanks a bunch

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sounds like you already have a plan try it and see what happens.

Sounds like a plan. Have you thought about -
how will he stay on the bike during your shoot? Will he put one leg on the ground, or you want him with both legs on the bicycle?
Think maybe creating some sense of movement by panning or something. Also when shooting try also much lower viewpoints - maybe you'll like them better.
Hope this helps.

GregBrave wrote in post #10629789
Have you thought about -
how will he stay on the bike during your shoot? Will he put one leg on the ground, or you want him with both legs on the bicycle?
Think maybe creating some sense of movement by panning or something. Also when shooting try also much lower viewpoints - maybe you'll like them better.
Hope this helps.

Actually, I was thinking he'll be standing, but panning, while he's moving sounds more interesting. Thanks, I'll try it.

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You welcome. Would be nice if you posted some photos from that shoot

It sounds like you're planning to shoot primarily with the left side of the model/bike towards the camera. This is total nitpicking, but you might want to swap that to the right side. My day job is working for a bike company, and having the non-drive side (the side that doesn't have all the gears) facing the camera is a cardinal sin. Even though this is a personal portrait, if your co-worker is a bike nerd, he'll probably appreciate it. Sounds like a fun shoot!

Thank you for the tip. We had to postpone the shoot, since he left on vacation until the end of the month.
Oh, well, it would be easier to do in September, since sun goes down earlier and I wouldn't have to stay up too late for that sunset sun.