I'm not sure there is a single answer to this. I would suggest that Winston sees a part of him, the greedy, selfish youth who took his sister's candy for himself and ran away. Besides being a selfish act, it is the last time he saw his mother and sister, although he does remember his mother protecting his sister, perhaps against him. Selfishness is probably part of youth; as you get older, there are often regrets about our selfish acts, particuarly, I would imagine, if we acted that way in our last contact with someone we loved.
Perhaps, and here's where I am "guessing," Winston has a foretaste of the selfishness that is going to lead him to denry Julia in the end. Toward the end of the chapter, Winston and Julia admit to each other that the party will break them, but that the party will never be able to make them stop loving each other. Could Winston already have understood that self-interest could make one do almost anything? I doubt that this happens on the conscious level, but it may be there bubbling under the surface.
And in the end, he is right.
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