New Girl: 10 Most Painful Break-Ups, Ranked

All the characters in New Girl have messy dating lives. Jess is a hopeless romantic who falls for guys too quickly. Nick wants love but is terrible at expressing his feelings. The player of the loft, Schmidt, struggles to win over Cece, who guards her heart carefully. Lastly, Winston strikes out with girls frequently.

These five friends bond over the difficulties of modern dating. They also help one another through the many break-ups they experience. Although some of the break-ups sit well with fans, many others are just painful to watch.

10 Nick And Reagan

When Jess is gone for jury duty, pharmaceutical saleswoman Reagan moves into the loft. Nick falls for her hard and fast. They begin a relationship and travel to New Orleans.

But, Nick and Reagan depend on Jess too much to fix problems in their relationship. When Jess leaves, they struggle to connect. So, Nick ultimately decides to end things with Reagan. To avoid conflict, he abandons her on a train, so their break-up is awkward but was a long time coming.

9 Winston And Daisy

Before Winston starts dating Aly, he has many bad relationships that often end with the girl cheating on him. One of these relationships is with Daisy.

Winston asks Daisy to be his girlfriend, and she says yes. But, he discovers that she’s involved with someone else and was mainly using him. It was painful to see Winston cheated on again, even if the breakup worked out for the best. Plus, Winston takes her cat Ferguson, so there was at least one positive result from the break-up.

8 Nick And Caroline

Nick and Jess are both are recovering from bad break-ups in the pilot episode. His relationship with Caroline is a toxic one. She continuously leads him on, and he fails to communicate his feelings to her adequately.

In the episode “See Ya,” Nick almost moves in with Caroline. But, he but backs out at the last minute. This is the right decision, but his actions hurt Caroline. Viewers find out in a later episode that Nick left her alone in the apartment without any explanation.

7 Jess And Paul

Jess breaks up with her boyfriend of six years, Spencer, at the start of the series. It takes her some time to get over it but when she does, her first relationship after is with the sweet teacher Paul.

But, Nick lets it slip to Paul that Jess doesn’t love him. At that moment, the three of them get locked outside on a balcony together. Jess and Paul break up as Nick is stuck watching the event on the sidelines.

6 Nick And Julia

In the first season, Nick meets the tough lawyer Julia. Their relationship goes pretty well until she goes on a business trip. While Julia’s away, she sends Nick a cactus.

Nick freaks out, thinking the cactus is a test. He panics and ends up killing the plant before leaving Julia a lot of weird voicemails, which leads to their break-up. It’s painful to watch Nick sabotage his relationship because of his insecurities, and it’s also very relatable.

5 Cece And Robby

After Schmidt breaks up with Cece, she starts dating Robby, who is an average but really nice guy. But, in the episode “Eggs,” Cece learns that she has to start trying right away if she wants to have children.

Cece tells the news to Robby, and the two break up because they’re at different points in their lives. Cece’s fertility issues are distressing for fans. She also rushes into an engagement, which fails because of her feelings for Schmidt.

4 Sam And Jess

After losing her job, Jess wants to have a meaningless fling. She pretends to be Sam’s blind date, Katie, when she meets him at the bar. After learning Jess’s true identity, they continue to hook up and eventually start a relationship.

The first break-up they have is worse than the second. After Sam discovers that Nick and Jess kissed, he punches Nick and breaks up with Jess. While this is for the best, Sam is heartbroken, and Jess feels guilty for cheating on him.

3 Jess And Ryan

Jess is excited to start her new job as vice-principal. However, her crush on the British teacher Ryan complicates things. Jess and Ryan begin dating, but he eventually has to move back to England.

They try long-distance, but Ryan misses a lot of Jess’s phone calls. The last straw is when he fails to attend the trip to Portland with her. Their break-up is unfortunate because it’s so realistic as sometimes distance doesn’t make the heart grow fonder.

2 Schmidt And Cece

Once Cece walks into the loft, Schmidt is immediately smitten. The two have an on-and-off relationship throughout the series, so they break up multiple times. But their worst break-up by far is the one in season three.

Schmidt has to choose between Cece and his college girlfriend, Elizabeth. Cece is devastated when she finds out that Schmidt is dating them both at the same time. The two break up in a restaurant, and it takes her a long time to forgive him.

1 Nick And Jess

The central romantic relationship in New Girl is the one between Nick and Jess. Fans love their opposites-attract dynamic and after two seasons, they finally become a couple.

While they love each other, they don’t have a lot in common. Jess likes planning out her life, and Nick is more disorganized. They break up in the spot where they first kissed and this parallel crushes the hearts of fans. Luckily, Nick and Jess get back together at the end of season six and remain together as of the series finale.

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