ClueChick: real clues from a real chick

I don't respond to a whole lot of ads, and when I
do, I make sure that I think we're a good match. My
question is if I should definitely send a photo with
my emails or should I wait for the woman to ask for
one or to send me hers?

Unlike some questions I receive, this one doesn't have a single hard-and-fast answer. If you're drop-dead gorgeous, it probably won't hurt for you to send a photograph, unless the woman is very insecure and decides you're out of her league. In that case -- and I may be a bitch for saying this -- but good riddance. I don't say that because I don't think unattractive people should get laid but because I don't have a lot of patience for people who rate themselves so poorly (look for more on this tomorrow). If you're the type who really relishes being with people who are insecure, then this is your loss and you may want to hold off on sending a photograph until after she sends hers so she knows that even after seeing her pic, you're interested.

In general, though, if you're reasonably attractive, it is quite unlikely to hurt your chances of a successful approach, and there's a good chance that it will, in fact, help. I never respond to someone solely on the strength of his pic, but a good pic can make me more likely to respond to someone whose email is on the edge.

On the other hand, if your email sucks, it won't matter how attractive you look in your picture, because I'm just not visually-oriented enough that having a hot guy in my bed is going to offset the fact that he's deadly dull. And if you write me a good email but don't send a photo, I won't ding you for that. In fact, I would say approximately half of the people who have responded to my ads have not sent photographs, so it won't even be conspicuous if you do or do not send one.

If you're quite plain, don't photograph well, or are downright unattractive, you're in a tough spot, as you've probably noticed. I, like most women, am loathe to sound shallow, but if your photograph makes me recoil, your fabulously brilliant email is unlikely to be enough to get me over that reaction. I don't like this about myself, but I've come to terms with it. In your case, I suggest one of two possible approaches:

The first option is to include your photograph with your email and hope that it will eventually reach a woman who's into ugly, or who's more seduced by words than I am. This approach will save you the false hope of some exciting emails if she's only going to reject you later because you're funny-looking.

The second option is not to include your photograph and hope that by the time you do get around to exchanging pics, she'll be into you enough for your brain that your freakishly large nose or snaggleteeth won't be an impediment to a hot and sweaty rendezvous.

If you're not ugly but are just plain, I'd suggest the second approach, and I'd also suggest that you not bother looking online for hookups. Looking online for something serious, people look more for personality than looks, and in that case you may shine.

I don't know which of these approaches, for ugly guys, will work better, because I'm afraid that neither of them works with me. Hey, I admitted I'm shallow. I don't have to like it, but I don't have to make myself a liar over it, either.