Would be appreciated, and an encouragement for everyone to be more or less 'current'.

It would be nice but posting the date of upload does not mean the picture is current. On some other sites, people upload the same picture every week.

Would it be possible to put on the upload page to put a box to say when the pic was taken so people type it in (not very technically minded so this might be more hassle than its worth!)

I'm supportive of this as a concept but not sure I can offer a simple, incorruptible solution. It would certainly aid the problem you have of meeting someone to discover their picture was taken 15 years ago.... Interestingly, there are a few guys on here who have met lots and lots of people, but whose picture is very clearly not recent. As there is no negative feedback, are we all being too polite to say something? A Polish friend was staying with me recently and he arranged to meet a guy for a wrestle and the first thing he said to me when he returned was that the guy looked nothing like his picture! He left positive feedback as the guy was friendly, polite and a pretty good wrestler, but he then privately sent a message suggesting the guy ought to post a more recent picture. Sorry - a bit of a ramble, but hopefully I'm making sense!?

Sorry, I didn't mean to rate my own comment!

@pshawfocus: You're right it is far from being a perfect system, but it's the only thing that is technically feasible.

Photo descriptions now contain the date they were uploaded.