The speaker in the poem is J. Alfred Prufrock, a man who wants to profess his love but is unsure what the lady will say.
Although Prufrock seems to be talking to someone, he is really talking to himself as he wanders the streets of the city on his way to his lady. He is not sure what to say, or what she will say, when he tells her he loves her. Therefore he has an interior monologue with himself.
Streets that follow like a tedious argument
Of insidious intent
To lead you to an overwhelming question ...
The question, of course, is if she loves him.
Despite the title, Prufrock does not feel confident. He is not sure what will happen, and the reader can infer that his love might not be returned, or that he might worry that it is not. He does not seem to be a handsome playboy. He is not confident in love.