|Greetings from the Critique Club
Let me welcome you to DPC and congratulate you on your first entry. This image is a very nice start. You've been able to capture a very straight forward scene in an unusual way. The low perspective works very well here. You've used the technique of leading lines very well here as the lines of the bench, the foot and the arm all lead you to her face.
Composition: You've used leading lines and the rule of 1/3's effectively, bringing her face to the center of attention. The rough wood texture and sole of her shoe add interest without detracting.
There are, however, two items that do distract. The first is that the image is tilted to the right as shown by the leaning lightpost and meter in the background. Tilted images are quickly noticed and quickly take away from the image. This link will take you to a tutorial which explains how to correct the tilt. The second distraction is the busy background behind her head. You have already corrected it partially with a shallow depth of field. In this case, an even shallower dof would provide more separation from the subject and less distraction. An f4 or even f2.8 would probably get what you need here.
Technical: Your choice of settings worked for you, except for the dof background. The shot is in focus and the lighting works for this image. Black & white is a good choice for the mood of this shot as it emphasizes lonliness. The contrast is off on the white end as noted in your comments. You have many greys and shades into black, but the whites are not being used to your advantage. You can look at the histogram in Levels and make sure that the tones are represented from left to right. If you are missing any tones, place your arrows at the beginning and ending of your histogram to allow all the tones to be used.
Meeting the challenge: Your image clearly portrays the title of a Beetle's song. There is a homeless/destitute look to the woman that implies lonliness, but doesn't shout it.
Overall: You've captured an interesting slice of life from a strong perspective. There is much going for it, and with some editing changes could be even stronger. This is a wonderful start to your career at DPC, which should give you a feeling of fulfillment. I expect to see strong work from you in the future.