Picture imperfect

Dear Dr. Lovemonkey,

I hate to say this, but I think my problem is being too smart or maybe having too much expertise. For about a year I’ve been posting photographs of myself on Web sites for singles. I’ve been getting a good response whenever I post the picture.

I’m not the world’s most beautiful woman, but I have worked as a professional photographer’s assistant. I know a lot about lighting, angles, makeup, and all the stuff that it takes to make a person look their best in a photograph. Naturally, the photograph I’ve been using is quite flattering.

Unfortunately, after I meet the men who respond they invariably tell me that I don’t look like my picture. I don’t look that bad, but it is a well-done image that I’m peddling.

So, should I take another photograph that isn’t quite as attractive? Should I intentionally look as drab as possible? I am having a problem thinking that this is the solution to the problem. What do you think?

— Millie the Model

Dear Millie,

I’m going to assume the photograph that you’ve been using was taken in recent years. I say this only because of my extensive experience with obit pictures in the local daily, which are quite frequently circa the glory days of Tom Brokaw’s "Greatest Generation" (i.e., the 1940s). It’s always weird seeing someone who was 80 years old and residing in an assisted-living facility looking surprisingly like one of the Andrews Sisters in their heyday. Then again, if the relatives of the decease want the death notice to show what someone looked like when Amos & Andy still ruled the airwaves, who am I to quibble?

So, as long as you’ve not used an ancient photo, extensive prosthetics, or otherwise attempted to make your photograph totally unrepresentative of the way you actually look, there’s absolutely nothing wrong (and much right) about wanting to use a photograph that makes you look your best.

If the men you’re meeting through the dating Web sites seem disappointed with your real-life appearance, try putting as much effort into reproducing the photo look in real life when you first meet these guys. If this means staging the lighting at the initial meeting, by all means do. The idea is to get past that first encounter (where men are notorious for concentrating on the visuals) and getting them to know you, so they’ll also take in your charm and personality. The whole package will undoubtedly bowl them over.

Dear Dr. Lovemonkey,

I’ve known this guy who’s in my class at school for a few years now. I always liked him, but it was no big deal. Well, his girlfriend moved out of town a little while ago and he’s been really depressed. I’ve talked to him about it a few times, and as I’ve gotten to know him better, I’ve been getting a crush on him.

My question is, considering that he’s still kind of mourning his ex-girlfriend (who is pretty much out of the picture now and not returning), is it a good or bad time to make some kind of move for him right now?

— Wondering and Waiting

Dear Wondering and Waiting,

My advice would be to not make an overt move. Suggest that you do two things, however. First, think about what it is that you find attractive about him. Think about whether or not these attributes are real or a fantasy on your part. What do you have in common? Have you spent time with him when he was not mourning his girlfriend and you both enjoyed yourselves?

I fear that you’ve gotten to know him only in crisis mode and that this doesn’t tell you a whole lot about compatibility. The best thing you can do is to continue to be his friend. When his mourning has subsided, he may make the move himself. But right now he’s emotionally vulnerable (you sound the same), and the best thing would be to continue to get to know each other while gaining a sense of your mutual attraction in more sedate times.