So, challenge? Nah. When she says “I’m not photogenic”, all I hear is “no one good has taken my picture yet.” Makes it easier, really.
I don’t worry about the light, or the location, I’m not plagued by doubts or worries, I just show her what I saw when I decided to photograph her. Get her eyes to light up like I’ve seen them do, bring out that smile that tends to force one onto my face as well, the way she carries herself, relaxed, at ease even when she’s nervous about a camera in her face. The hair that frames her face just right.
We all show our personalities in our faces, in our whole bodies, really. It’s the personality I’m drawn to, drawn to show in photos. Further I get into all this here photography jazz, the more expressive I want my photos to be. The more I want my subject’s personality to shine through.
So I make she laugh, I make her cringe, I take her on a hike, show her a creek in the middle of the hills, make fun of tourists, engage and interact, all in service of bringing her personality out.
And maybe show her a hoarder’s house. I reckon that always helps get a shoot going.