In "What's Up With the Ending?", we talk about "The Lady with the Dog" raising more questions than it answers. This is also the case for Dmitri Gurov. The poor guy is confused – all the time – about himself, about women, about love, and in particular about Anna. When he returns to Moscow after the start of their affair, he wonders, "Had he been in love, then? Had there been anything beautiful, poetical, or edifying or simply interesting in his relations with Anna Sergeyevna?" (3.4) Shortly after, he sets off to the town of S. – "what for? He did not very well know himself" (3.14).
Fortunately, Gurov learns from his time with Anna. The confusion and defensive chauvinism of Section I are replaced with the mature understanding of Section IV, which allows our protagonist to draw conclusions not only about Anna, but about all of the women he slept with before her. Look at the following passages, taken from the beginning, middle, and end of "Lady with the Dog." They effectively trace Gurov's increasing awareness of himself and of women:
In his appearance, in his character, in his whole nature, there was something attractive and elusive which allured women and disposed them in his favour; he knew that, and some force seemed to draw him, too, to them. (1.5)
All the time she had called him kind, exceptional, lofty; obviously he had seemed to her different from what he really was, so he had unintentionally deceived her. . . . (2.40)
He always seemed to women different from what he was, and they loved in him not himself, but the man created by their imagination, whom they had been eagerly seeking all their lives; and afterwards, when they noticed their mistake, they loved him all the same. And not one of them had been happy with him. Time passed, he had made their acquaintance, got on with them, parted, but he had never once loved; it was anything you like, but not love. (4.15)
Gurov goes on to conclude that with Anna it is different, that this really is love for the first time. Which means that "kind, exceptional, lofty" man she thought he was is the man he has become.
Age is an issue from the get-go; Gurov reflects that "his wife seemed half as old again as he." Is it a coincidence that he next falls for a woman little more than half his age? (Anna is 22 in Yalta; Gurov is almost 40. The age difference doesn't escape him, as he makes a point of noting the gap after she departs on the train.) Perhaps he's trying to recapture his youth.
And in case you missed it the first two times around, Chekhov returns to the idea of age at the story's conclusion, when Gurov catches a glimpse of himself in the mirror:
His hair was already beginning to turn grey. And it seemed strange to him that he had grown so much older, so much plainer during the last few years. The shoulders on which his hands rested were warm and quivering. He felt compassion for this life, still so warm and lovely, but probably already not far from beginning to fade and wither like his own. (4.15)
If, at the story's start, Anna was to Gurov merely a fresh, young face, she isn't any longer. He recognizes that she's aging (or will be shortly), and goes on to conclude that he loves her deeply, anyway. Yet another layer in our transformation cake.
With his classification of women as "the lower race" to his over-developed class-consciousness, Gurov can occasionally come off as pretty judgmental. Consider the way he views his wife: "She read a great deal, used phonetic spelling, called her husband, not Gurov, but Dimitri, and he secretly considered her unintelligent, narrow, inelegant" (1.5). Later, at the theatre, he notes that "as in all provincial theatres, there was a fog above the chandelier, the gallery was noisy and restless; in the front row the local dandies were standing up before the beginning of the performance, with their hands behind them" (3.25).
So…what's the point? As with many Gurov characteristics, this, too, is changed by Anna. For despite her "provincial" environment, Gurov loves her nonetheless:
When Gurov looked at her his heart contracted, and he understood clearly that for him there was in the whole world no creature so near, so precious, and so important to him; she, this little woman, in no way remarkable, lost in a provincial crowd, with a vulgar lorgnette in her hand, filled his whole life now, was his sorrow and his joy, the one happiness that he now desired for himself, and to the sounds of the inferior orchestra, of the wretched provincial violins, he thought how lovely she was. (3.26)