Virginia Woolf carefully portrays a man who has many human foibles but also balances those flaws with some sympathetic characteristics. Oliver Bacon, from an early age, learned how to persuade well-to-do women to enter into questionable deals with him. To begin his ascent in commerce, he literally sold them "stolen dogs." By the story's end, he has figuratively been on the receiving end, but as a willing buyer. These figurative "dogs" are the Duchess' fake pearls. Bacon pays for them twice: once with money, and once with his integrity because he knows it is a bad bargain.
Oliver has worked hard to become an expert in his field so people respect his expertise. If one were seeking a knowledgeable jeweler, Bacon would be an excellent choice.
Bacon has also developed all the cultivated tastes he needs to surround himself with luxury and comfort, and to converse knowledgeably with his clients. He seems to have few genuine friends. Oliver would be hard to get to know so it is difficult to say definitely how enjoyable his company would be.
Woolf describes the gaps on Bacon's life; he is not satisfied yet. He seems to continue holding onto the sadness he knew so well. Woolf asks,
"Was he not still a sad man, a dissatisfied man, a man who seeks something that is hidden?"
What he seeks is a good match, which will secure a place in the elite—for himself in the short run and, most likely, for whatever future child he might have.
Oliver is appealing in his devotion to his mother's memory, but this reverence seems to occupy the emotional center that friends or a romantic partner would usually fill. One hopes for Oliver that Diana will be a gentle soul who will accept him, but one is likely to be apprehensive as well that she might reject a relationship built on mutual deceit.