There is not much you can do if you (like me) just plain and simple “don’t photograph well”, except invest time and money in professional photo’s. Or if you’re lucky enough to have a friend who is a pro or highly skilled amateur photographer, ask them if they’d consider doing your pics in return for dinner/babysitting/some non-cash reimbursement.

I’ve sucked it up and spent hundreds of dollars over the past years on 2 different sets of professional photo’s so that I at least have a few photo’s where I look decent and accurately represent my looks.
Evan’s advice to get candid/action photo’s taken by friends unfortunately just does not work for me – about once in 10 years I’ll look OK in a candid pic; the rest of the time I pretty much look like hell in most candid pics.

I still don’t get much attention online, but at least I’ve done about the best I can in the “recent and accurate photo” department. My advertising is truthful! Which is not the case in many online profiles in my experience.

The one thing I haven’t tried is professional “boudoir” photography – as fun as it sounds (I have friends who’ve done it) I have the feeling that using those pics online may attract the exact people I would prefer to avoid…

If you do present better “in person” than “virtually”, then do as much socializing “in person” as you can – don’t rely on online dating sites as your sole or major method of meeting people. And if you happen to get some good “smiling & having fun” pics taken while you’re socializing IRL, then add them to your online profile.

And make sure that the text of your profile totally rocks, so that if some one does like your pics enough to read further, they will be entertained/inspired by what they see.