If it's important to you to know what your penpal looks like, send your own picture first.
One of my most irritating experiences since I started penpalling came with someone I'd been exchanging long letters with for weeks. At the end of one of her letters she rather bluntly asked me to send a photo the next time I wrote. As it a) didn't seem like that big a deal, and b) it seemed like the only way of keeping the correspondence going, I sent her a picture along with my (again) rather long letter. Naturally I assumed she'd be reciprocating at some point. Yes, you're probably way ahead of me - I never heard from her again. It's enough to make a guy paranoid - anyone would think she didn't like my face or something...
Of course we just have to accept that penpals may suddenly stop writing for any number of reasons (including slightly shallow ones!) but my big regret in that instance was agreeing to her rather cheeky request for a picture. What had made it cheeky was not just the curt way she asked me, but that she hadn't as a matter of courtesy sent her own picture first. So my first suggestion on penpalling etiquette is this - if it's important for you to know what someone looks like, simply send them your own photo. In fact, it's debatable whether it's even necessary to ask for a photo in return - nine times out of ten people in that situation will feel honour-bound to send one.
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