Any Jessica Day might make up her own songs on a regular basis, the roommates also constantly sing to one another. One of Jess' go-to artists is Taylor Swift. She uses Swift's music to get through arguments with significant others, wallow in her feelings, or pump herself up for a night out. Even Schmidt references his "Taylor Swift-like range of emotions" to Cece, showing that Jess isn't the only one who's a fan.
When Taylor Swift guest-starred on the series in the second season, she didn't play herself as Prince did in the third. As a result, the series never got particularly meta with her music. It's a shame because plenty of her songs are great ways to describe some of the relationships in the show.
Schmidt And Cece: Paper Rings
When the audience first meets Schmidt and Cece, they aren't shy about their vanity or their materialistic natures. They have a lot in common - working hard for their nice things, being more interested in hook-ups than lasting relationships, and being willing to do anything for their best friends.
Schmidt and Cece fall into a romantic relationship after attempting a purely physical one. They have a lot of ups and downs but find that, if they're together, nothing else matters. That's essentially the same message of Taylor Swift's "Paper Rings," in which the singer, "hates accidents, except when we went from friends to this."
Nick And Caroline: We Are Never Ever Getting Back Together
Nick repeatedly trying to get back together with his ex Caroline in the first season, and then leaving her with no explanation in the finale, are not some of his proudest moments. He matures a lot after that first season, and this song might as well have been their anthem once he leaves her for good.
Caroline seemingly moves on with her life but also becomes obsessed with finding out why Nick left her, as is highlighted in a season 3 episode. "We Are Never Ever Getting Back Together" could easily play in Nick's head when he runs into her in later years considering all of the drama the two put one another through.
Russell And Jess (And Nick): The Way I Loved You
There are only a handful of love triangles in the series. This isn't exactly one. After all, Nick encourages Jess to date Russell before he ever its his own feelings for her. Jess thinks she wants a mature and even-keeled relationship but finds that there's just something missing with Russell. There's no ion.
Just as Swift's narrator laments, "Screaming and crying and kissing in the rain," Jess has that ion in her friendship with Nick, but not her romance with Russell. It's something she doesn't see right away, but it's something that's echoed later in the series by another one of Jess' boyfriends, Sam, when he realizes that Jess won't truly commit to him because she's still in love with Nick. The narrator of "The Way I Loved You" might not be able to get back to the same relationship, but Jess eventually does.
Coach And May: Stay, Stay, Stay
May only appears in a handful of episodes of the series. She meets Coach and the gang on a Valentine's Day bar crawl. Despite their initial differences, Coach and May find they have so much in common that they decide to try getting to know one another better. May makes Coach work for the relationship though, and when she gets a job offer for New York, he goes with her.
It might seem strange that a song called "Stay, Stay, Stay" belongs to the couple that leaves the show, but the title is more about staying in the relationship than in one place. Despite the ups and downs they face, the two work well together and fight for their relationship to succeed.
Winston and Walt: Superman
While Taylor Swift's discography is full of break-up songs and celebrations of love, "Superman" can also be heard as a story of idolizing someone who may or may not actually be as "super" as the narrator thinks. The song's narrator sees a guy as going off to "save the world or go to work, it's all the same to me," in his suit everyday.
Winston looks up to Walt Miller and adores him as the father figure he didn't really have. While Nick sees his father as the con man he is, Winston sees Walt as someone who took them on adventures and could do anything. Walt is his Superman, even when reality shuts the idea down.
Nick And Reagan: The Story Of Us
Reagan and Nick don't initially seem like a good fit, but they end up in a surprisingly successful (at least for a time) relationship. A successful woman who can give Nick his space, Reagan isn't as manipulative as some of his previous girlfriends. Nick initially likes that Reagan doesn't force him to talk about things, but then their relationship starts to break down.
Lines from "The Story Of Us," like "miscommunications lead to fallout" are a perfect assessment of the ending of Nick and Reagan's relationship. Just as Nick wants to open up, Reagan pulls away. Of course, he also leaves her on a train, so their story is even more dramatic.
Schmidt And Associated Strategies: It's Time To Go
In the early seasons of the show, Schmidt is pretty obsessed with his job. He tries hard to impress his boss, sets out to one-up his competitive co-workers every chance he gets, and repeatedly attempts to prove that his marketing ideas are the best. He's not always successful, but he still appears to love it. That changes after the time skip in season 7 when he's taken time away to be a stay-at-home-dad while Cece's career path changes. When he goes back to work for the first time, he realizes just how much his priorities have changed.
The underrated "It's Time To Go" from Taylor Swift's Evermore chronicles a similar idea. It's about knowing when the right time is to let go of old relationships and commitments. It takes Schmidt until nearly the end of the series to realize that his job isn't what he wants, but he gets there.
Winston And Aly: Invisible String
One of Swift's newer songs, "Invisible String" dropped as part of Folklore in 2020. Not a single, it might not be as familiar as a song like "Cardigan," but its lyrics tell the story of two people who find themselves destined for one another, tied together with some invisible string.
When Winston first meets Aly, she's assigned as his senior partner on the police force. He's had a string of bad relationships, just as the narrator of the song. Aly intends to keep their relationship strictly professional, but can't help becoming friends with him, and eventually more.
Nick And Jess: Fearless
If it was love at first sight for the main couple of the series, "Everything Has Changed," might have fit them better. Even "Endgame" might be appropriate. Considering that their relationship, however, makes the two of them overcome all of their insecurities about romance, "Fearless" seems more apt.
Nick doesn't like commitment after Caroline, but Jess makes him think about things in the long term. Jess prefers relationships with structure, but Nick makes her embrace the unexpected. They would both likely agree that the other drags them, "headfirst, fearless."
The Roommates Of 4D: Long Live
Taylor Swift writes a lot about love. This isn't so much a love song as a love letter to the people and the memories that accompany her rise. "Long Live" recounts the experiences she had in her early days of performing in sold out stadiums. One of the most often ed lines is, "I've had the time of my life fighting dragons with you."
While the inhabitants of apartment 4D might not have performed sold out shows, they did once sing with Prince. There are no actual dragons to slay, but the metaphorical ones are there throughout the show. When they finally leave the loft behind in the series finale, this particular song would be a fitting tribute to the group who spent so much time living and learning together.