“Repeated and bitter experience had taught him that every fresh intimacy, while at first introducing such pleasant variety into everyday life, and offering itself as a charming, light adventure, inevitably developed, among decent people (especially in Moscow, where they are so irresolute and slow to move), into a problem of excessive complication leading to
an intolerably irksome situation.”
Here, Dmitri explains that while he has had many love affairs, none of them have ended well and none of them have been particularly fulfilling. Given the fraught relationship that Dmitri has with his wife, it can be deduced that he has a pessimistic outlook on love and romance that has colored all of these affairs. One can assume that Dmitri has had a string of shallow dalliances with women in order to distract himself from his monotonous life but that he has ultimately come to regret every one of them.
“And only now, when he was grey-haired, had he fallen in love properly, thoroughly, for the first time in his life.”
This quote is also an acknowledgement that Anna is the first and only woman that Dmitri has ever loved. This sentimental and moving realization exists in stark contrast to the messaging of the previous quote. Dmitri has clearly been transformed through loving Anna, so much so that the man who thinks this quote is virtually unrecognizable from the bitter cynic that the reader is introduced to at the start of the text.