Ana,
I recently saw this again, and in answer to Bobby's future, it occurred to me one way to answer is from a psychological perspective. To be clear I do not mean that is the only way to answer, but it is one.
The overall relation of Bobby to his family, including his father and siblings, is important, of course. As is the way he relates to his friends and acquaintances.
But it occurred to me his relation to the women in his life is very illuminating.
His mother. I find it interesting that the film, I believe, is totally devoid of any mention of Bobby's mother. Even the scene of family member pictures on the wall did not seem to include a single one of someone who could have been his mother. She is never mentioned. From this one can assume she must have died or left very early in his life. The way this may have affected his development, and his future relationships with other women, is therefore an issue.
Rayette. On the surface, and to the casual observer, Rayette is not only simple but almost simpleminded. But I don't think that is really accurate. I think she certainly gets that Bobby appreciates, up to a point, her warmth and attention. And then he doesn't. This would be confusing to the most aware and intelligent people, yet she wants to stay with him. I also think she gets how conflicted and alienated he feels about his past and his family, but again does not seem to come up with a way to find a way forward with him.
Catherine. While not literally the polar opposite of Rayette's persona (both have a warmth and generally easygoing manner), in many ways she is obviously quite different. What is interesting about her is that Catherine is very much of the kind of upper middle class background that Bobby ran away from years before, yet now seems to want someone of that sort. Or does he? It is interesting that he is both attracted to her, but also does things he must have realized she would find off putting, like the argument about his playing the Chopin piece.
I tend to think after my most recent viewing that the argument about that piece was in part based on him not totally accepting the validity of Catherine's point of view, her critical knowledge of music. So, did his provocation come from something argumentative in him, or was it his real view of his playing versus her approval of it? Hm, it could of course be something of both, but imo definitely the latter was part of it.
Catherine after all is a student of music, who I think from Bobby's perspective does not have a valued and knowledgeable opinion about music. While finding her physically and even socially attractive (on teh surface she would seem to have more in common with him than Rayette does), he does not wholly trust her. In that connection he finds it virtually ludicrous that she would want to marry his brother and live on the island in that house, that environment.
And of course Catherine finds Bobby to be quite problematic as well. In the end it is not mere circumstance that prevents them from being together. They in fact are ill suited, and Catherine does not provide an "answer" to his needs.
Patina. As his sister she of course is not even in the ballpark of any long term relationship other than as such. Bobby loves her in his own way, I think is clear, but he sees her goofiness and related problems. He is closest to her in the family, but she does not serve as a substitute for his absent mother.
In short I think Bobby has issues in how to relate to women, most likely due in large part to his mother's absence from his life. And from that psychological pov that is not likely to change unless he goes into therapy, which in turn is unlikely. As a result he will likely end up going through a series of failed relationships with women, subconsciously seeking an answer that for him does nto really exist.
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