He had begun being unfaithful to her long ago – had been unfaithful to her often, and, probably on that account, almost always spoke ill of women, and when they were talked about in his presence, used to call them "the lower race." (1.4)
Compare this to the story's conclusion and consider how greatly Gurov has been changed by his relationship with Anna.
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)
Gurov is not only transformed by his love for Anna, but educated by it as well. The ignorance that characterizes him in the earlier stages of the story will by replaced with a sense of awareness and wisdom in its conclusion.
Anna Sergeyevna looked through her lorgnette at the steamer and the passengers as though looking for acquaintances, and when she turned to Gurov her eyes were shining. She talked a great deal and asked disconnected questions, forgetting next moment what she had asked; then she dropped her lorgnette in the crush. (2.3)
We can tell from Anna's nervous actions that she knows what's coming. It's almost as though she's already given in to the affair, before it has taken place.
[…] he told Anna Sergeyevna how beautiful she was, how fascinating. (2.33)
Does Gurov really feel this way at this point in the story, or is this just part of his seduction?
He was genuinely warm and affectionate with her, but yet in his manner, his tone, and his caresses there had been a shade of light irony, the coarse condescension of a happy man who was, besides, almost twice her age. (2.40)
Gurov still has his reservations about Anna, even after he's begun falling in love with her.
She sat down in the third row, and 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. He thought and dreamed. (3.26)
Anna has completely transformed the way Gurov thinks about women.
In another month, he fancied, the image of Anna Sergeyevna would be shrouded in a mist in his memory, and only from time to time would visit him in his dreams with a touching smile as others did. (3.3)
Gurov is completely unaware of the depth of his feelings for Anna.
Had he been in love, then? Had there been anything beautiful, poetical, or edifying or simply interesting in his relations with Anna Sergeyevna? And there was nothing for him but to talk vaguely of love, of women, and no one guessed what it meant. (3.4)
Gurov doesn't know what love is because, as he concludes at the story, he's never been in love before – even with his wife. This naiveté explains much of his confusion when it comes to Anna.
He was under forty, but he had a daughter already twelve years old, and two sons at school. He had been married young, when he was a student in his second year, and by now his wife seemed half as old again as he. (1.4)
This passage suggests that Gurov's reason for pursuing Anna has something to do with his fear of growing old.
But at every fresh meeting with an interesting woman this experience seemed to slip out of his memory, and he was eager for life, and everything seemed simple and amusing. (1.6)
A large part of the reason for Gurov's seducing Anna has to do with dissatisfaction with his own life.
Her expression, her gait, her dress, and the way she did her hair told him that she was a lady, that she was married, that she was in Yalta for the first time and alone, and that she was dull there... (1.7)
It's interesting that Gurov immediately characterizes Anna as bored, since this is actually his own boredom is actually the reason he pursues an affair.
Gurov told her that he came from Moscow, that he had taken his degree in Arts, but had a post in a bank; that he had trained as an opera-singer, but had given it up, that he owned two houses in Moscow. (1.17)
It's clear that Gurov feels stifled in his existing life; contrast his passion for the arts with his job at a bank.
As he got into bed he thought how lately she had been a girl at school, doing lessons like his own daughter. (1.18)
The age difference doesn't escape Gurov's notice. Compare this passage to the one at the story's conclusion, when he again considers Anna's age in light of his own.
The solitary candle burning on the table threw a faint light on her face, yet it was clear that she was very unhappy. (2.13)
This line is later echoed when Gurov leaves Anna in the theatre in S. Anna is persistently characterized by this constant unhappiness, both before and after she falls in love with Gurov.
He was tormented by an intense desire to confide his memories to some one. (3.4)
This desire reflects how severely Gurov is at a loss to understand his own feelings.
That morning at the station a poster in large letters had caught his eye. "The Geisha" was to be performed for the first time. He thought of this and went to the theatre. (3.23)
Remember that Gurov once trained to be an opera singer. Think about the way Anna is associated with the unfulfilled, artistic part of his life.
She was walking alone, always wearing the same béret, and always with the same white dog; no one knew who she was, and every one called her simply "the lady with the dog." (1.2)
Anna is very much separate from the rest of the Yalta crowd; she is isolated in the sense that no one knows who she is or anything about her.
One did not know what to do with oneself. (2.1)
Consider the way the environment drives action in this story…
I have been tormented by curiosity; I wanted something better. 'There must be a different sort of life,' I said to myself. I wanted to live! To live, to live! . . . I was fired by curiosity . . . you don't understand it, but, I swear to God, I could not control myself; something happened to me: I could not be restrained. (2.17)
It is ironic that Gurov is driven by the very same curiosity – yet Anna doesn't recognize this commonality and feels isolated from her lover anyway.
Gurov felt bored already, listening to her. (2.18)
Similarly, Gurov too fails to recognize that Anna is driven by the same "curiosity" that he himself felt earlier in Yalta.
He was moved, sad, and conscious of a slight remorse. This young woman whom he would never meet again had not been happy with him. (2.40)
Gurov is conscious of Anna's unhappiness, but he fails to recognize it as similar to his own dissatisfaction. The two lovers are further isolated by this lack of understanding between them.
Little by little he became absorbed in Moscow life, greedily read three newspapers a day, and declared he did not read the Moscow papers on principle! He already felt a longing to go to restaurants, clubs, dinner-parties, anniversary celebrations, and he felt flattered at entertaining distinguished lawyers and artists, and at playing cards with a professor at the doctors' club. (3.2)
Though not explicit here, Gurov's new loneliness is evident through his need for constant company.
Gurov went without haste to Old Gontcharny Street and found the house. Just opposite the house stretched a long grey fence adorned with nails.
"One would run away from a fence like that," thought Gurov, looking from the fence to the windows of the house and back again. (3.16-7)
This is the first time Gurov really makes an attempt to identify with Anna, to see the world from her perspective.
And he judged of others by himself, not believing in what he saw, and always believing that every man had his real, most interesting life under the cover of secrecy and under the cover of night. All personal life rested on secrecy, and possibly it was partly on that account that civilized man was so nervously anxious that personal privacy should be respected. (4.11)
This is a sad thought – how truly isolated each man would be if he had to hide that which was most valuable to him. It's no wonder Gurov feels as alone as he does.
The lady looked at him and at once dropped her eyes.
"He doesn't bite," she said, and blushed. (1.9-10)
Anna is immediately characterized by a sense of modesty; this renders her later indiscretion all the more shocking, and all the more indicative of a major shift in her character.
In the evening when the wind had dropped a little, they went out on the groyne to see the steamer come in. There were a great many people walking about the harbour; they had gathered to welcome some one, bringing bouquets. And two peculiarities of a well-dressed Yalta crowd were very conspicuous: the elderly ladies were dressed like young ones, and there were great numbers of generals. (2.2)
Chekhov doesn't let us forget the social context in which Gurov and Anna's affair takes place.
Then he looked at her intently, and all at once put his arm round her and kissed her on the lips, and breathed in the moisture and the fragrance of the flowers; and he immediately looked round him, anxiously wondering whether any one had seen them. (2.7)
Even in the lax atmosphere of Yalta, Gurov can't forget the restrictions of society and the threat his relationship with Anna poses to his reputation.
The hotel porter gave him the necessary information; Von Diderits lived in a house of his own in Old Gontcharny Street – it was not far from the hotel: he was rich and lived in good style, and had his own horses; every one in the town knew him. The porter pronounced the name "Dridirits." (3.15)
Gurov is definitely concerned with social status and reputation – through the narrative perspective we can see that he's judging those around him (in this case, the porter and his pronunciation).
"So much for the lady with the dog...so much for the adventure....You're in a nice fix...." (3.22)
Gurov recognizes that things have fundamentally changed since Yalta. If he is to lose Anna now, it must be under entirely different circumstances.
Anna Sergeyevna, too, came in. She sat down in the third row, and 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)
After months of judgment and superiority complexes, Gurov admits that he judges Anna as below his class – and that he loves her anyway.
She glanced at him and turned pale, then glanced again with horror, unable to believe her eyes, and tightly gripped the fan and the lorgnette in her hands, evidently struggling with herself not to faint. Both were silent. She was sitting, he was standing, frightened by her confusion and not venturing to sit down beside her. The violins and the flute began tuning up. He felt suddenly frightened; it seemed as though all the people in the boxes were looking at them. (3.30)
Notice that Gurov doesn't feel the shame of their affair until Anna reminds him of it.
And Anna Sergeyevna began coming to see him in Moscow. Once in two or three months she left S., telling her husband that she was going to consult a doctor about an internal complaint – and her husband believed her, and did not believe her. (4.1)
It's interesting how details like this – or the reaction of Gurov's wife, for example – are completely glossed over. It's as though they just don't matter to the two lovers.
"It's a good thing I am going away," she said to Gurov. "It's the finger of destiny!" (2.35)
Anna is simply trying to justify she and Gurov's unfortunate circumstance.
"I shall remember you...think of you," she said. "God be with you; be happy. Don't remember evil against me. We are parting forever – it must be so, for we ought never to have met. Well, God be with you." (2.39)
Again, Anna's guilt manifests itself in these ideas of fate, of what must be, of what ought to have been.
The train moved off rapidly, its lights soon vanished from sight, and a minute later there was no sound of it, as though everything had conspired together to end as quickly as possible that sweet delirium, that madness. (2.40)
Notice that Gurov adopts the same fatalistic attitude that Anna did before she left.
Here at the station was already a scent of autumn; it was a cold evening.
"It's time for me to go north," thought Gurov as he left the platform. "High time!" (2.41-2)
Gurov's mood is very much a product of his environment; this is why he feels the need to change locations once Anna leaves.
What savage manners, what people! What senseless nights, what uninteresting, uneventful days! The rage for card-playing, the gluttony, the drunkenness, the continual talk always about the same thing. Useless pursuits and conversations always about the same things absorb the better part of one's time, the better part of one's strength, and in the end there is left a life groveling and curtailed, worthless and trivial, and there is no escaping or getting away from it – just as though one were in a madhouse or a prison. (3.12)
There's something fatalistic in this passage, as though Gurov has no control over the circumstances of his life.
He was sick of his children, sick of the bank; he had no desire to go anywhere or to talk of anything. (3.13)
Anna has completely changed the course of Gurov's life – he's unable to return to normalcy after their affair.
He considered: to-day was a holiday, and the husband would probably be at home. And in any case it would be tactless to go into the house and upset her. If he were to send her a note it might fall into her husband's hands, and then it might ruin everything. The best thing was to trust to chance. (3.18)
But as Gurov soon finds, trusting to chance isn't possible. Part of his transformation in "Lady with the Dog" is about actively pursuing what he wants – in this case, Anna.
He walked up and down, and loathed the grey fence more and more, and by now he thought irritably that Anna Sergeyevna had forgotten him, and was perhaps already amusing herself with some one else, and that that was very natural in a young woman who had nothing to look at from morning till night but that confounded fence. (3.19)
Metaphor much? Anna is hemmed in by her fence the same way she and Gurov are each hemmed in by their marriages.