Dermot Mulroney returned to New Girl as Russell, Jess's fancyman ex-boyfriend, and upon running into Jess and Nick in the middle of their first date, exclaimed, "Glad to see this is finally happening!" Word, Fancyman, word. Even though Jess and Nick's first official date was more awkward than awesome, the important thing is that it happened; sure, neither Nick nor Jess seemed at all pleased with where they ended up at the end of the night, but tentative first steps were taken and all that.
Or, you know, fourth steps. After all, Jess and Nick have had their first kiss and their make-out sessions. They did their touchy-feely-supportive-partner thing at Nick's dad's funeral. For all intents and purposes, they fit the definition of a romantic couple in everything but name, a situation that lends itself well to creating the sort of confusion and chaos Schmidt and Winston feared could destroy the good chemistry of the four roommates, and prompted Nick to continue his trend of being a Responsible Adult by asking Jess out on a real date.
Or not. After a smooth (and touching!) rehearsal with Tran (Hi, Tran!), Nick fumbled through the ask with Jess and wound up woefully overdressed for what Jess assumed would be a friendly stop at a sidewalk food cart, not a formal dinner at a total swank-fest. I was okay with overdressed Nick, though. Jake Johnson cleans up fiiiiine.
Also, LOL at "wearing Schmidt."
Jess and Nick's first date quickly mutated into three separate outings that seemed to act as a microcosm of their entire relationship this season. Confused about the nature of their dinner, Jess rolled with it. She didn't understand whether it was a date or dinner with a friend, or why Nick was so dressed up—not to mention incapable of accurately communicating his intentions to her—but it worked because what happened at the restaurant was basically the early days of Jess and Nick's relationship on a smaller scale.
Then Fancyman showed up. To anyone else, it would have been a random encounter with a former romantic interest: mildly uncomfortable, but not necessarily an evening-killer, considering Russell and Jess parted on somewhat amiable terms. It's not like one of them cheated or he was some kind of creepy stalker-ex. They simply realized that they weren't as compatible as they thought and ended the relationship. It sucked and it was sad, but those things happen all the time.
Still, the blast from Jess's past upset the tentative balance between Jess and Nick and they ditched the fine dining for date number two: drinking at the bar as friends. They were more at ease with one another, firmly back in their respective comfort zones, with the bar stop representing the stability of their relationship prior to The Kiss That Changed Everything in "Cooler." After getting good and drunk on booze and each other's company, Jess and Nick decided to stick it to the past and return to the table they'd fled in order to finish their real live date... which brought them right back to confronting the current state of their relationship... which again, neither of them was adequately prepared to do.
Cue Russell with an assist, whipping out two pens ("That's the move, right there!") and paper and making Nick and Jess write down in secret what they thought their date meant. His decision to ultimately NOT share their scribbles with the rest of the class raises two possibilities:
1. Russell was counting on Nick and Jess writing similar answers that confirmed their mushy soulmate status and decided not to risk crushing them with the truth when their beliefs didn't align.
2. Russell planned to leave them in the dark the entire time in an attempt to force Jess and Nick to communicate honestly with each other—an essential aspect of any healthy and successful relationship and one that Jess and Nick haven't yet managed to master.
Personally, I'm pulling for door number two just because the idea of Nick and Jess NOT being on the same page is too sad, and between Jess's conversation with Cece and Nick's with Tran, it appears that Nick and Jess DO share the same feelings. They just suck at sharing those feelings with each other.
Regardless of Russell's intentions, the truth about what Jess and Nick wrote remained elusive, and even though they managed a heart-to-heart of sorts on the sidewalk where they resolved to stop doing the things the other one found arousing—Jess asking Nick for help and Nick gargling his beer—once they got home, they couldn't help but fall back into their old habits. However, rather than act on their feelings, they each went their separate ways, even though it clearly made them both miserable.
While the good ship Nessy (Nick + Jess + messy) got caught in the doldrums, back on dry land, Winston and Schmidt prepared for the eventuality of that ship docking in a safe harbor. Their ploy to destroy Nick and Jess's date in the name of saving the dynamics of the loft eventually came to involve Outside Dave (Steve Agee) after Winston recalled his worst dating experience ever: a tableside serenade by a homeless dude. They bartered a deal where Outside Dave would give Nick and Jess the same treatment in exchange for twenty-five minutes of TV time and a homemade sandwich, but TV time turned into lavatory time and rather than work together to ruin date night, Winston and Schmidt had to work together to get Outside Dave out of their bathroom.
In addition to worrying about a Jess/Nick relationship ruining their living arrangement, Winston and Schmidt had a much more personal motive for keeping Nick and Jess apart: They didn't think they were capable of being friends with one another without Nick to bring them together. It was a ridiculous notion, even with the flashback evidence to confirm their apparent incompatibility, because we've seen them get along just swell without Nick throughout the series, especially in recent episodes. Even though the moral of the story—that Winston and Schmidt ARE friends with one another and are perfectly capable of surviving without Nick around—was a given from the very beginning, it was still satisfying to see them arrive at that conclusion themselves, especially since Nick and Jess are stuck in a rut at the moment.
What did you think of "Date Night"?
– One-liner of the night: "Whiskey was a nickel! Whores caked in mud!" —Nick, on the Old West
– Nick: "I have a question about my clothes." Schmidt: "Burn them. Burn them all."
– Among Schmidt and Winston's plans to sabotage Jess and Nick's date, Winston proposed stabbing Jess with a knife and shooting a bear full of Hep-C and setting it free in the restaurant. I like your just-a-touch-too-much style, Winston.
– I wasn't aware that the Pledge of Allegiance could be sexual. You learn something new every day.