Many of us have (or will have at some point) a less than flattering photo floating around on the internet. It happens. The most annoying thing of being a photographer is knowing when someone is taking a photo of you that will look bad -- or that you never see until everyone has seen it.
Many photographers -- especially the designated "family photographer" takes on that job because they are most at ease behind the camera rather than in front of it. This is fine -- but before you know it there are tons of fun photos showing everyone -- except the person who always takes the pictures! Learning to take a photo or to have a photo taken of you is a skill. I know of a few people who must have practiced their "look" in front of a mirror to get it just right. Every shot of them that I see -- there they are with the same exact smile and tilt of the head. It is funny. Sure they look great -- but it gets to be funny.
I try to be extra careful with the photos I put out there of other people -- making sure that they are flattering. If I am shooting someone candidly I keep my camera on continuous shooting to make sure I get a flattering image and not one with eyes closed, mouth in an odd shape, or -- well -- worse. The most flattering way to take a portrait shot is to sit below the photographer -- OK shoot down on someone's face. Also make sure the subject is not tense and pulling his chin in toward his neck. Push your chin out (but don't look like it is exaggerated). This stretches out the chin and neck area and is flattering to everyone.
Watch the lighting -- harsh light is not good. If you do need to shoot or be shot is bright, harsh light; use a fill flash to counter any weird shadows created by the light. If you are taking photos of someone outside on a bright day -- use that fill flash. A subject in a cap will need that for sure to light the area under the bill of the cap. If you don't their eyes will be in shadow.
The photos above was taken at a photo show -- the background is less than perfect. Since it was at a photo show this is OK. But that line going through my head does big me a little. I did crop it down to just me -- my photo was high above my head. The room was dark -- so lighting was an issue and this was a flash photo. All in all -- not bad. My friend Carla, the director of the show, took the photo. The best thing to do when someone is going to take your photo -- relax.
Beware of flash in a low light condition. This can bring out the red eyes. If someone is in low light, their pupil is dilated and this contributes to the red, glowing eyes seen in many photos. The red eye reduction flash counters this by flashing once prior to the shutter release to cause the pupil of their eye to contract. Also turning on a light behind the photographer can help. When the subject looks toward the photographer, they look to the light and their pupil contracts.