I think it’s perfectly ok to ask for something, using your honest desire as basis for the formulation, given that you graciously accept the reply. For instance, I wouldn’t find it ridiculous at all to simply ask

“I would like to have a picture of you to associate with your address information in my filing system to help knowing for sure whom I am corresponding with, do you have a picture I can use?”

It’s important to

1. be genuine
2. straight forward, the simpler the message the better
3. keep all vague things and value words out (such as “perhaps”, “I would _really much_” or “would it be possible”). All that just distracts and creates a complicated mess of a question.

There is a lot of power from using genuine feelings and needs in communication. I can heartily recommend the book “Flawless Consulting” by Peter Block for a more indepth look.

At my old office someone often posted photos after parties and such. I would go through copy faces from the photos to paste into Address Book (because I am so freaking productive!). That way I’d see people’s photos in Mail when I got a message from them.

One day our finance manager was in my cube and I opened an email she’d sent earlier so I could grab a fact from it. She saw her photo there and thought it was so weird. It was awkward, like she thought I was stalking her. I had to open other emails and show her that it wasn’t just her who’s photo I’d taken. Then she thought I was just insane generally instead of in a targeted way.

Anyway, good idea to ask first!