Some comments..(we don't do brutality here, for that you have to go to DPReview !).
I think it's pretty ok, for a first shot. OK, two areas, one technical, one emotional. The background is a bit distracting. Methinks you hung something behind her, and with the creases and things, it detracts. Find a nice neutral background, can be darker with a blonde subject, use a very narrow depth of field, thus blurring out the background nicely.
Personally, I don't much like for soft focus blurry effects on the face. Take a normal shot. Short Tele lens (80-100mm), f 2.8 or so..Crisp and sharp, focus on the eyes. It's a bit seventies to be soft-focus. Perhaps, you might rather try to selectively sharpen the hair and clothing and not the facial features. Many women don't like every wrinkle brought into sharp focus !
Emotionally however, is where the secret of a great portrait really lies. I try to get to the depths of the soul of every person I take a portrait of. I talk to them, make them think, laugh, consider - and then I take the picture when I think I understand who they are. If a portrait does not reflect the soul, then it becomes a superficial skin and bones shot, a barbie figure.
Well, that's my 2 cents. You lighting is nice, maybe you need some more mood. Hope this was of some help...well done and keep clicking!!
Here are some things I would try. First move your subject further from the background if you have room. Focus on the eye's of the subject and be sure they are sharp. Using a narrow DOF is fine if you have the eye's in focus, that allows the background to be soft, as it should. The subject in this instance appears to be leaning into the camera and this is not the most flattering of poses. Start with a 3/4 pose, that is, having the left (or right) shoulder closer to the camera with the person turning their head slightly.
If you like the soft focus look use a gausian blur on another layer or two and then recover the eye's, lips and eye brows so that they are still sharp. Scott Kelby has an excellent tutorial in his book The Photoshop CS Book and there are others available on line for free.
The subject looks rather starey eyed as if she were not relaxed. She is a pretty lady and with a different pose this would come across better. You have used butterfly lighting on this image which is fine. I would experiment with other styles of lighting as well to give more modeling to the face. This of course if you have more than one light. I would also experiment with window light and fill flash as well, perhaps using a reflector or two.
Certainly I am no expert but did want to share a few things that might help.
Thank you all for the time and effort you have put into your replys Peter could you talk about this statement more "Emotionally however, is where the secret of a great portrait really lies. I try to get to the depths of the soul of every person I take a portrait of. I talk to them, make them think, laugh, consider - and then I take the picture when I think I understand who they are. If a portrait does not reflect the soul, then it becomes a superficial skin and bones shot, a barbie figure" Once again thank you all this is what I started with
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the lighting is natural light and a bounced flash, the white materal behind her is just a portion of the waiters jacket cloned over and over.
I did have another thought when I learned that you had used a bounce flash. The butterfly shadow beneath the nose indicates that the bounced flash was the primary light source with the natural light being the secondary. Have you tried pointing your flash up at a 45 or 66 degree tilt and then pulling up your little white card to reflect some light directly into her face. This often gives a soft and fairly even light. Also, if you have your camera on M and cut down the exposure about one stop it will make the background darker than the subject for a pleasing look. This would especially be true if you opened your lens up enough that the background fell out of focus. Even in a crowded restaurant the subject can be made to stand out. These are just thoughts and things that you might try. It was creative of you to clone the waiters jacket but you might have been able to find something of a darker shade to do that with. You could also lift the subject completely out and put her in another background entirely using PS.
By the way, I like the unedited version better since the subject is more in focus. I hope you take my suggestions in the spirit I have given them, that being one of sincerly offering something that might be of help.
First I want to commend you for having the nerve to post a first attempt at a new style of picture -- I know how difficult it can be to go out on a limb like that. I'm thankful, though, that this is a safe place to do that.
You've got a beautiful model to work with here, no doubt. Assuming she's willing, you will have other opportunities to explore this type of photography.
I agree with Gordon that the original is more pleasing, and I think for the same reason: the soft edges are a bit much for this picture, although I can certainly understand the need for them given what you did with the background.
Gordon - thanks for posting the info you did. That helps all of us learn from your experience.
Good to hear from you. Wow so much great stuff here thank you Gordan for all your advise it is very much appreciated If you look at my web site you ll see that I'm pretty much a bird and flower guy. One of the hardest things for me to do is to approach people and ask if I can take their picture Isn't that just so odd. This was a family friend at a dinner party so it was a little easier, but I must tell you after I have rarely felt such satisfaction (except the time that eagle and falcon were next to each other David ) So Gordan if I understand you correctly do you feel that I should have a little more light on her face ? And I'm not sure what you mean about a white card to accomplish this. What I was really trying to do with the blurring effect was to give her hair kind of a subtle flowing effect I'm sure you have seen the waterfall picture with the water blurred. I had seen a magazine picture like that and thought that I could reproduce it. Although very pretty she is 52 and had a few wrinkles on her forehead and around her eyes I thought that the blurring would help with that problem. Anyway thank you all I can't wait to try my next portrait and with all this great help I'm sure it will be better.
I use the gausian blur to good effect on many of the people pictures I take so in that regard I agree with you. This is especially true for older people. It is my opinion that where you could improve is the application of blur yet still maintaining sharpness in the eyes, lips, eyebrows, clothes and hair. Blur the skin and background. Scott Kelby's book The Photoshop CS Book gives a great tutorial about that. As it applies to hair, I am not a fan of bluring that but of course this is just my opinon and it is no more valid than yours.
You have plenty of light in her face but where the problem comes is that the main part of it is coming from above. This puts shadows in her eye sockets, under her nose, and in the smile lines beside her mouth and under her lips. You could mitigate that by using a small white card taped to the back of the flash and sticking up a couple of inches above the flash head. The SB80 and SB800 have this white card built in to the flash and you just pull it up. News photographers use this trick all the time in taking flash pictures. I hope this helps.