Smoking in the Gazebo

I've always considered my portrait shots to be pretty weak,

honestly. Any suggestions would be greatly appreciated.

I like the tones. The only thing is the background, where that pole cuts right across your subjects nose. The background is overall a little busy.

Also, would consider using fill flash or a reflector to fill in some light on the face, or have the person turn a bit to have a little more light on the face. It loses some impact in the higher contrast of the rest of the picture.

I'm guessing you are going for the natural - not overstylized type of portrait... which I personally think is the best.. Take what I say and mix it with your own vision - is my first advice.. So, here I go with my own opinion and style... I'd turn the subject so no light hits her face.. as sun spots are distracting on a woman's face in particular... A sheet or reflector to bounce some light... (or look for light colored house nearby or light concrete - or glass - or something natural that the subject is not distracted by (therefore keeping a natural look and more comfortable subject)- nearby bright reflective objects will bounce the needed low fill light into the front... Then, I'd shoot at a 2.8 - or 4 - for out of focus background!!! I almost always shoot wide open for portraits - unless the background has some significance. Also try some full body and some chest up and some where the face fills the frame. Shoot a whole roll trying different angles and compositions. Your image does have a mood - which is key... just keep shooting... You'll know you have it when you get the result you are trying for.

If you have an FM-10, you can find some real bargains in lenses. You definitely need a moderate telephoto, not a zoom. Look for used Nikkors which are AI or AIS. The AI are always cheaper (except AIS Series "E"), and you don't need AIS. Especially look for Series "E" lenses. Some used AIS lenses are more expensive than current AF lenses, but what you are looking for is a 100mm f2.8 AIS Series "E", or a 135mm f2.8 AI or AIS Series "E". Then use it like Mary says. All this is confusing probably, but the point is these lenses are in the 100-150USD range, and will make you an overnight portrait whiz. One of the hidden benefits of the FM-10.

I'm going to go out on a limb here and suggest that this subject had no idea the photographer was taking her picture. If this was the case then all the positioning and lighting was dictated, not chosen. How would you (anyone) suggest dealing with that?

Ok so everyone has valid suggestions for how to shoot candid portraits. But to address the last comment- the best way to improve composition, and often times the lighting is to change the camera position. LOL, now granted that isn't going to take the place of a bounce card- but fill flash should be and ok compromise. All in all my opinion of street photography is to shoot and see what you get. Manipulating street shots just doesn't seem 'right'. I would have liked to have seen her exhale some smoke in this shot. Thanks