Heartbroken over her cheating boyfriend, Jessica "Jess" Day moves in with three single men, Schmidt, Nick and Coach to get over her breakup. The guys try their best to get her out of the apartment and back into the dating life with the help of Jess' best friend Cece but end up with more than they expect because they find themselves truly caring for her as a friend.
Jess accidentally breaks the television after a spontaneous living room basketball game; Nick and Schmidt try to convince Jess to retrieve her TV and personal belongings from the house she had shared with her now ex-boyfriend. After Coach leaves, the original fourth roommate Winston returns and attempts to manipulate Schmidt into switching rooms since Schmidt now occupies Winston's original and larger bedroom.
Nick is worried that he will run into Caroline his ex-girlfriend at a mutual friend's wedding the guys were invited to and asks Jess to be his date/pretend girlfriend. At the wedding, Winston takes his job as usher far too seriously and Schmidt attempts to woo Brooke a former highschool crush, but also catches the eye of his sexually abusive "frenemy" Gretchen.
Nick suffers a blow to his self-esteem when Jess walks in on him naked, before his date with his coworker. Meanwhile, Winston gets obsessed with learning pop-culture references online for his job interview.
Jess invites Paul, a fellow teacher on whom she has a crush, for Thanksgiving dinner at the apartment. Everyone warms up to Paul except for Nick. Cece becomes attracted to Schmidt while he is cooking Thanksgiving dinner. .
Jess gets jealous when Winston joins her troubled-youth handbell quartet and instantly becomes a natural. Meanwhile Nick and Schmidt engage in class warfare when the toilet breaks and they each have their own idea of how to get it fixed.
When Jess decides to take her relationship with Paul to the next level, she consults with the guys for some sex advice. Meanwhile, Schmidt worms his way into his boss' baby shower to compete with his office female counterpart.
Jess agrees to throw Schmidt's 29th birthday party in school bus as a party bus. She also invites her boss Tanya (Rachael Harris) to the party. Nick introduces his new girlfriend Julia (Lizzy Caplan) to the gang.
Nick panics when Julia (guest star Lizzy Caplan) doesn't want to put a label on their relationship. Meanwhile, Jess enlists Julia to help her get out of a traffic ticket, Winston reconnects with a former booty call (guest star Kali Hawk) and Schmidt is baffled as to why his shower towel is always damp.
Against Nick's wishes, Jess makes it her mission to get the loft's cantankerous landlord (guest star Jeff Kober, "Sons of Anarchy") to like her. In doing so, she inadvertently jeopardizes their living situation and the guys are forced to admit they've made some "unofficial" changes to the apartment. Meanwhile Schmidt tries to decipher what he thinks are mixed signals from his boss Kim (guest star Gillian Vigman).
Single for the first time on Valentine's Day, Jess convinces Schmidt to be her wingman as she attempts to have an attachment-free fling with a handsome stranger. Nick's romantic plans are foiled when he finds himself spending more time with Julia's law firm assistant than with her. Winston becomes one of the girls when Shelby invites him over on the holiday.
When Jess tries to intervene with a classroom bully she finds herself the target of the bad seed student. Schmidt, meanwhile, is thrilled over his post-Valentine's sexcapades, but hates that his paramour wants to keep it a secret; and Nick goes into a tailspin when Julia sends him a cactus.
When Nick is hurt playing a game of touch football and Jess discovers he doesn't have insurance, she brings him to her doctor friend - an OB-GYN. The gang rallies together and Nick evaluates his life when his seemingly innocuous back injury may prove to be more serious than thought.
Jess disagrees with a student's father, Russell (Dermot Mulroney), on the child's priorities. When she goes to confront him about it, she ends up falling for him instead. Nick decides that he doesn't need a cell phone. Winston tries to impress Shelby by proving that he knows more trivia than Schmidt does.
Jess and Russell go on their first date, but Jess feels uncomfortable afterward when Russell gives her mixed signals about their relationship. Nick's old college roommate, Dirk (Martin Starr), visits and encourages Nick to date younger female college students. Winston finally gets the nerve to tell Shelby how he feels about her. Through an unusual set of circumstances, Winston finds out about Schmidt and Cece's relationship.
Winston spills the beans about Schmidt and Cece's relationship and the news finally spreads to Jess who does not take it well. Jess decides the roommates should be free with their secrets and gets more than she bargained for. Meanwhile, Nick goes to Schmidt for dating advice.
After spending an entire week at Russell's place, Jess returns the favor by having Russell stay over at the apartment with the guys for a weekend. The weekend however does not turn out as planned. Winston gets his dream job, when he is hired to work for his favorite sports radio host (Phil Hendrie), who turns out to be a short-tempered jerk. Kareem Abdul-Jabbar makes a cameo appearance.
Jess meets Russell's ex wife (Jeanne Tripplehorn) and agrees to watch their daughter, who develops a crush on Nick. Cece is scared that she is pregnant with Schmidt's child. Nick dates an artsy college student (Chloe Bridges), who is a lot younger than Nick thinks. Winston tries to get his boss on the set of a talk show hosted by Michael Strahan.
Jess fears she and Russell don't share the fiery passion he exhibits with his ex-wife Ouli. Meanwhile, Cece is not yet willing to admit her true feelings for Schmidt, so she encourages him to go on a date with one of her Russian model roommates. Then, a down-in-the-dumps Nick channels all of his energy into a new vegetable garden.
When Jess and Nick run into their exes Paul and Caroline, the gang fears they both may "backslide" into romantic relationships. Meanwhile, Schmidt desperately tries not to get aroused as he deals with a delicate medical issue, Winston suffers the consequences of a wild night out with his boss and Cece brings Schmidt to a nursing home to meet her grandmother.
When one of the roommates decides to move out of the loft, the gang makes an unexpected trip to the desert where Winston faces his fear of the dark, Cece and Schmidt's relationship reaches a turning point and Jess and Nick square off with a coyote
Jess is fired from her teaching job. Schmidt throws a party at Nick's bar, in celebration of his penis cast being removed. A new side of Winston is revealed after he drinks some of Nick's fruity concoctions. Cece introduces her new boyfriend, Robby (Nelson Franklin) to Schmidt.
Jess meets Sam (David Walton), a handsome stranger who thinks she is his blind date; A regular (Raymond J. Barry) at Nick's bar claims he is Nick from the future and Winston's mother Charmaine (Anna Maria Horsford) and sister Alisha (Keenyah Hill) visits. Schmidt is determined to sleep with Alisha.
Jess and Nick evaluate their friendship, after Nick is convinced that Jess is only using him as a platonic boyfriend. Elsewhere, Schmidt hopes to impress an attractive Republican by pretending to be one of Mitt Romney's sons. Winston has random sexual fantasies, due to Shelby refusing to have intercourse with him for many weeks.
Jess begins to have genuine feelings for Sam as more than a sexual partner, after seeing him work as a pediatrician during the day. Nick reunites with Amelia (Maria Thayer), an ex-girlfriend from college. Schmidt intrudes on Cece and Robby's Halloween date. Winston feels it is finally time to break up with Shelby.
Still unable to find a new job, Jess blames her problems on premenstrual syndrome. Winston also thinks he is suffering from same symptom as Jess, even though he is a man. After meeting a strange old man in the park, Nick decides to be less angry. Schmidt agrees to be consensually sexually harassed by his new boss, Emma (Carla Gugino). Cece is bothered after Robby labels her a "nice girl"
Jess' divorced parents (Jamie Lee Curtis and Rob Reiner) come over to the apartment for Thanksgiving; Jess tries to get them back together despite numerous failed attempts in the past. Schmidt's cousin (Rob Riggle), also named Schmidt, comes over, spurring a manly competition between the two.
Jess is in her thirties and she begins to worry about wanting to have children before it's too late. Schmidt is bothered by being unable to satisfy Emma during sexual intercourse. Nick finally decides to sit down to begin writing his zombie novel.
Tired of taking showers, Jess and Winston decide that they want to put a bathtub in the loft. However, their attempts makes matters worse causing them to fool Schmidt by faking a robbery. Nick meets Angie (Olivia Munn), a tough and beautiful stripper with a hotheaded boyfriend. Schmidt struggles between having sexual relations with Emma and trying to win Cece back.
The gang attends several Christmas parties on Christmas Eve. Sam tries to win Jess back. Nick is intimidated by Angie being very sexually adventurous in public. Schmidt rejects Cece's Christmas gift after she denies him after he proclaimed his love for her.
When Nick's con-man father (Dennis Farina) suddenly reappears, Jess tries her best to fix the two men's relationship, despite Nick's fears that he's being used in another one of his dad's gambling schemes. Meanwhile, Schmidt teams up with Robby to try to win back Cece.
When Nick is convinced that one of Jess' students is hiding a nefarious secret, he goes undercover in her adult night school class. Meanwhile, Winston has an embarrassing encounter with Cece, causing an examination of all the loft-mate's peculiarities.
Jess is considered to be a cool force when she goes out with the guys, so they go out to find women and leave her at home. Jess hears noises outside and asks the guys and their dates to return. Party games begin, and Nick has to kiss Jess.
Jess gets fed up with her parking spot after she finds a neighborhood homeless man and cats sleeping on her car in the same week. Schmidt concocts a plan to get a new parking space in their building and shares it with Nick and Jess. Causing them to later battle it out for the coveted parking spot. During the competition Nick and Jess will get some alone time to discuss their relationship.
Jess catches the eye of a professional football player (Steve Howey), with whom Winston is trying to land an exclusive interview for his radio station. Meanwhile, Nick and Schmidt argue over the planning of their "TinFinity" party celebrating their tenth anniversary of living together, and Cece gets a surprise offer.
Jess comes to a conclusion about her romantic feelings for Nick and she struggles to tell him. Schmidt becomes obsessed with buying a fish, which Winston sees as a metaphor for Schmidt's unresolved feelings toward Cece. Nick plans a bar promotion to impress the bar owner.
When a death occurs in Nick’s family, Jess, Schmidt and Winston travel with Nick to the Windy City to help him with the funeral preparations and meet his boisterous family members, including his mom, Bonnie (guest stat Martindale); his younger brother, Jamie (guest star Kroll); and his Boston cousin, Bobby (guest star Burr).
Jess and Nick, who are caught between friendship and something more, try to break out of relationship limbo by going on a “first” date. Once Schmidt and Winston realize a full-on Jess/Nick romance might be happening, they swoop in to try to sabotage the date.
Jess decides to throw Cece a surprise bachelorette party while Nick and Winston awkwardly take her fiancé, Shivrang, out for the night. Then, as Schmidt desperately tries to find a real girlfriend in time for the wedding in order to get a “plus one,” he is forced to seek out his old girlfriend from his “fat Schmidt” college days.
In a series of flashbacks, Jess, Nick, Schmidt, Winston and Cece tell one another how they each lost their virginity. Not surprisingly, when they realize the stories directly affect their present day sex lives, one relationship will change forever.
Jess’ dad chooses the worst day to pay the loft an unexpected visit, forcing a nervous Nick to spend time alone with him. Meanwhile, Jess gets a shot at a big new job on the day before Cece’s wedding. Then, Schmidt struggles to publicity date a less-than-physically-ideal woman, and Winston continually psyches himself up for his huge surprise birthday celebration, which no one seems to remember to throw for him.
Cece’s wedding day finds Jess and Nick making a decision about their relationship. Meanwhile, Schmidt schemes with a typically overenthusiastic Winston to sabotage the nuptials, although a shocking announcement may be bigger than anything he plans.