Although Nick is the character in the novel least likely to be accused of such a quality, Nick can be considered careless for dating Jordan and for getting stone-cold drunk.
A man from the West with quality values dating a rich, lying, gossiping, speed-demon like Jordan Baker? Obviously Nick doesn’t have marriage in mind here. How careless of him to waste his time with such a woman. One can just hear Nick’s parents spouting, “Son, I’m very disappointed in you.” Look at the irony in this scene:
"You're a rotten driver," I protested. "Either you ought to be more careful or you oughtn't to drive at all."
"I am careful."
"No, you're not."
"Well, other people are," she said lightly. ... They'll keep out of my way," she insisted. "It takes two to make an accident."
"Suppose you met somebody just as careless as yourself."
"I hope I never will," she answered. "I hate careless people. That's why I like you."
Even with something as bad as this that disgusts Nick enough to spout to his girl, Nick still continues dating her! The irony is that even though Jordan like’s Nick because he’s NOT careless, the very fact that he’s dating her MAKES him careless. One can imagine Jordan smirking at the end of this scene, … corrupting the hometown boy. Shameful!
To a lesser extent, Nick can be considered careless for getting drunk and losing composure at the end of Fitzgerald’s “Chapter 2” of the novel.
I have been drunk just twice in my life and the second time was that afternoon so everything that happened has a dim hazy cast over it although until after eight o'clock the apartment was full of cheerful sun.
Every year, this carelessness of Nick’s leads to the most asked about sentence in the entire novel:
. . . I was standing beside his bed and he was sitting up between the sheets, clad in his underwear, with a great portfolio in his hands.
Yes, folks can do some crazy things when they aren’t in complete control of their faculties. Such carelessness!
Early in the novel, Nick states that his father left him with this advice: "Whenever you feel like criticizing anyone," he told me, "just remember that all the people in this world haven't had the advantages you've had."
Nick's lack of judgement towards Gatsby cause him to become careless. Nick becomes blinded with Gatsby and his lifestyle that he becomes careless in his views towards the other characters. This is not to say that his final judgements towards Daisy were not correct but he stratigically leaves Gatsby out of the final judgement and actually ends up feeling sorry for him.
Nick prides himself on his own honesty. However, he repeatedly aligns himself with Gatsby, who is entirely fabricated. In addition, Nick knows Jordan is careless and dishonest, but he falls for her anyway.