“This is definitely not Montgomery, Alabama. Tell me. What would you do if it was? If this turned out to be another Montgomery?” asked Guitar.
“Buy a plane ticket.” replied Milkman.
“Exactly. Now you know something about yourself you didn’t know before: who you are and what.” (104)
This scene imposes a very significant relationship between Milkman’s background and the experiences the rest of the people have to deal with. His background is one of a high-status person. Milkman grew up in the most prestigious house on Not Doctor Street. His father, Macon, is the most privileged of the colored people and seems to hold a status even with white people. He uses his job as a means of imposing his superiority due to his wealth. Also, his grandpa, Dr. Foster, was a doctor and happened to be the richest person in the community. Not Doctor Street is a haven Milkman was raised in where he experiences the vastness as opposed to others. Not Doctor Street has a different context when applied to the Southside setting. Southside hones the partying atmosphere and involves a society almost entirely of black people, just like Milkman. However, people living near Southside don't have the same issues as Milkman does on Not Doctor Street. The different locations serve people of different backgrounds, and the idea isn't brought to Milkman until now.
Milkman and his family have never needed to depend on anyone for survival. Money has always been accessible to the family. However, most people Milkman interacts with are black people who are struck by the racial prejudices and don't find the means for increasing their position. Milkman clearly doesn't fit in the same category because both sides of his family are privileged enough to diverge from such problems.
Guitar, his own best friend, emphasizes the differences Milkman has with the rest of the population. The very fact that Milkman says he will buy a plane ticket to escape issues in Montgomery reveals the ease of decision-making and lack of interaction with racial prejudices. His family has raised him in a privileged atmosphere which makes his behavior alien to the people around him. Racial bias seems to be an issue, but Milkman denies its importance by claiming he can buy a plane ticket away from a problematic climate. His reaction to such a prevalent concept causes Guitar to doubt his seriousness and ability to comprehend things beyond what he is accustomed to. That could be a reason why Guitar was hesitant to tell Milkman about the Seven Days because the response might be inappropriate.
Overall, Milkman's privilege causes him to diverge from the rest of the community. He has been raised in a family where money is plentiful and life doesn't demand much work. This gap, which Milkman especially creates after claiming to "buy a plane ticket," further sets him apart from everyone and everything, including his own family.
Notice how, in Pa. and Va., Milkman slowly loses all of his possessions, especially those connected to his persona back in Michigan, which you have sketched here: his suit, his shoes, his watch, his luggage--all are lost. By the time we see him in camo fatigues on that hunting trip, it's like we wouldn't even recognize the guy you're describing here. His quest to find himself first means losing "the things that weigh him down" (as Guitar says elsewhere).
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