Well, pretty safe to say that he is going to eventually hit that home-run with her. Just don't think he realizes quite ye that it isn't going to be in a game of baseball.
@Hounder I wonder what kind of bet he loses on to have to propose to her? Sadly for him he doesn't realize victory is easily accomplished and within reach by simply holding her hand.
The manga is named 'kono natsu' ('this summer'), a reference to a new (started in January) baseball/time travel (which I suppose is why Nishikata yells 'time slip' when he pitches) manga named 'ano natsu: 1959' ('that summer: 1959').