Nick Miller is oftentimes a bit of a mess. He has a lot of growing up to do during the seven seasons of New Girl. His relationships sometimes reflect his need to grow as he dates women who have their lives together and correct his inaccurate assumptions of events.
None of the women he dates are unintelligent, but some do point to his regressive behavior as they lack emotional intelligence, or are naïve to the ways of the world.
9 The College Students
It might seem unfair to lump several women together, but it's a little difficult to get a read on most of them since Nick doesn't usually spend more than a night at a time with any of them. Instead, Nick gets advice from Schmidt on how to date multiple women at once and how to easily get rid of women he decides he's not interested in.
As a result, there are several young women Nick spends time with at the end of the first season of the show. Some of them even know each other. None of them appear to be particularly knowledgeable when it comes to the reality of dating men who aren't in college like them. They fall for his excuses and are impressed by the fact that he has a job as a bartender. Only a few of the women even realize that he's dating more than one of them at a time.
8 Amanda
Amanda only appears as a love interest for Nick in one episode of the first season, so it's difficult to get a good impression of her. On the one hand, she's got a knack for sarcasm and decent knowledge of classic music. She's also a bartender, which speaks to some great memorization skills.
On the other hand, Amanda is not so great at reading people. She doesn't understand Nick's discomfort on their first date, and she frequently seems confused at the statements he makes, despite often making cryptic sarcastic statements to him too. Amanda seems like she's very smart in a handful of areas, but could use some help to really understand the people around her.
7 Angie
Like Amanda, Angie is one of Nick's early interests in the series. She appears in a handful of episodes in the second season as a customer at the bar that Nick is intrigued by. Angie is all impulse. She frequently jumps into situations without thinking, just like she jumps into a relationship with Nick.
Also like Amanda, Angie isn't great at reading Nick's cues. She doesn't realize that he wants a real relationship with her instead of to just have fun with her. Angie demonstrates her inability to read those cues when she contributes to some of the worst moments for Nick on the show: trying to switch partners with Jess on a trip to a cabin and leaving in the middle of the night.
6 Amelia
A young woman Nick knew while he was in college, Amelia attempts to reconnect with Nick in the second season of the show during the first Halloween episode. Unlike both Amanda and Angie, Amelia does pick up on Nick's cues.
She knows exactly how Nick felt about her when they were in college, but she waited for him to make a move instead of pursuing anything with him. By the time she meets back up with him, however, they're very different people, and Amelia fails to realize that until Nick tries to be honest with her about them not working together.
5 Kai
The audience is told that Kai is brilliant, but the audience also never really gets to see Kai in action. She's a wealthy person who owns and maintains her own business, but Nick goes through a brief time of believing she's homeless.
Why? Kai does things like hang out around his apartment all day and sleep with newspapers all over her. A lot of her actions don't make sense for someone who should be running her own company. Kai does, however, demonstrate that she understands how to motivate Nick when she picks activities tailored to what they have in common - and when she offers to pay his salary for the night so he doesn't have to go into work. With their shared interests, it seems like Kai and Nick are a perfect match, but they meet just when Nick is starting to want more, making them doomed from the start.
4 Shane
In the middle of the second season, Shane briefly takes over as manager at the bar, prompting a change in behavior from Nick. He starts trying a little harder to do his job well, wanting to make a good impression.
Shane isn't a bad manager as she wants to inject new life into the bar. She does make a few bad decisions though, like dating (however briefly) an employee and allowing that employee to come up with "Guy's Night" as a promotion for the bar. Despite her business degree, Shane thinks that allowing guys (who make up most of the bar's customer base) to drink free and having the kitchen prep messy platters of nachos for them is the way to boost sales.
3 Julia
While Nick dropped out of law school with just a few semesters to go, Julia graduated and became a lawyer. She's not just any lawyer, but a corporate lawyer at a large firm who has her own intern assigned to.
Julia is more observant than most of Nick's other exes, picking up on the things he doesn't want to tell her, or the things he doesn't want her to know. She's also one of the few girlfriends who picks up on something going on between Nick and Jess, even though neither of them want to admit it.
2 Reagan
In a lot of ways, Reagan is the smartest of Nick's exes. She's pragmatic, understanding the reality of her job and weighing the pros and cons of the conflicts that come up in her personal life as a result of her traveling so much for pharmaceutical sales. Reagan is also incredibly knowledgeable about the items she sells. She's consistently at the top of her game and ends up getting a promotion.
Where Reagan lacks intelligence is reading the room. While she's able to see that Nick is interested in her pretty early on, she doesn't see how uncomfortable going to Jess for help in their relationship makes the latter. She also doesn't see when their relationship is going downhill fast because she doesn't open up to Nick, and she fails to see that he's regressing so much that he leaves her on a train. On paper, she's incredibly smart, but her emotional intelligence could use some work.
1 Caroline
Caroline is the first ex of Nick's that the audience meets. She is objectively bad for him, there's no question. She also, however, is one of the smartest women he interacts with, but some of her smarts come from knowing him longer than anybody else he dates.
The two meet while he's in law school and date on and off right up until a few months before the pilot episode. Caroline, as revealed in the pilot script, though never explicitly stated in the show, works in public relations. She's very good at her job and very good at reading people. Caroline manages to manipulate Nick into thinking he has a chance with her multiple times. They even get back together at one point as she sees him as the most familiar, and the best option for knowing her future.
Caroline, however, also knows after only having met Jess briefly that Jess is the reason Nick decides not to commit to her at the end of the first season. She knows how to get under his skin to get a real answer out of him, and she knows when to walk away from the relationship when it isn't working. Caroline uses more common sense than any of the other women that Nick dates.
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