Why should Jordan Baker be with Nick in The Great Gatsby?

This is certainly an intriguing, opinion-based question. One could argue for or against the idea that Jordan Baker should be with Nick. The two characters have many similarities. They are both outliers--two individuals who do not fit within common social constructs of the time. Nick has chosen not to follow in the footsteps of his family's lucrative hardware business, instead testing his prowess as a bond broker. He leaves behind a potential fiance and moves...

This is certainly an intriguing, opinion-based question. One could argue for or against the idea that Jordan Baker should be with Nick. The two characters have many similarities. They are both outliers--two individuals who do not fit within common social constructs of the time. Nick has chosen not to follow in the footsteps of his family's lucrative hardware business, instead testing his prowess as a bond broker. He leaves behind a potential fiance and moves to the East Coast to pursue life as a bond broker. Jordan Baker does not follow social constructs of becoming a wife and mother, and instead is an accomplished and rather famous golfer. They are both independent and bent on making their own way in the world. 

Nick is certainly intrigued by Jordan from his first meeting with her. He talks about her pleasing face and graceful manner. Later on in the novel, they become confidantes and co-conspirators in trying to unravel the mystery of Gatsby. 

Both Jordan and Nick play a cursory role to the events that unfold around them. Neither of them is the cause nor the solution to the events of Gatsby's passions and Daisy's carelessness. They are witness to it all, but not able to affect the outcomes in any way. 

Their commiserations could provide a basis for a relationship, and their mutual respect and admiration for each other may sustain that relationship for a time. But their similarities might ultimately make them ill-suited for a romantic relationship. Both are independent and fiercely guarding their rights to live in worlds of their own choosing, apart from the gilded cages in which other characters in the novel find themselves.