Джесс и Рассел идут на первое свидание, но Джесс чувствует себя неуютно, когда после встречи Рассел посылает ей смешанные сигналы об их отношениях. С помощью необычного стечения обстоятельств, Уинстон узнаёт об отношениях Шмидта и Сиси.

Джесс предполагает, что между Расселом и его бывшей женой Оли до сих пор присутствует сексуальное напряжение, поэтому она пытается вызвать у него такие же чувства. Ник пытается выращивать помидоры. Сиси признаётся в любви Шмидту после того, как его госпитализируют после сексуального инцидента с её соседкой по комнате Надей.

As Jess' job search kicks into high gear, the guys fear her time of the month is also affecting their physical and psychological well-being. Meanwhile, Schmidt begins a "50 Shades of Grey"-type of relationship with his corporate boss, and Nick gains wisdom from an unlikely, hands-on (and mute) source.

Jess catches the eye of a professional football player, with whom Winston landed 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

Nick struggles to throw Jess the perfect birthday party, while Schmidt works overtime to help out Cece in her new job as bartender and Winston and Coach engage in a bake-off.

Nick and Jess try to keep their breakup a secret; Winston passes the police academy entrance exam and demands a celebration.

Jess, Coach and Ryan attend a teachers' conference, led by education guru Brenda Brown. Back at the loft, Nick, Schmidt and Winston try to have a wild weekend while Jess is out of town.

When a new bar opens in the neighborhood, it completes the final piece of the puzzle for Nick's epic Valentine's Day pub crawl. Meanwhile, Jess and Ryan drunkenly contemplate their future, Coach meets a new woman - over and over again - and Schmidt tries to fit into the world of politics.

A beautiful pharmaceutical rep enters the gang’s life when she agrees to sublet Jess’ room while she is on jury duty.

On the night before the wedding, Nick and Winston try to help Schmidt re-write his vows and Jess, thinking that Sam is going to propose to her, rallies the gang into playing True American to avoid giving him an answer.

When Schmidt and Cece and Winston and Aly invite Jess on their couples glamping trip, members of her singles-only group tag along. Meanwhile, Nick struggles with the next chapter of his New Orleans-set novel after Schmidt gives him "no notes".

When Jess insists on covering Robby's medical bill, she is stunned after finding out the total and goes to extremes to find a way to help pay. With Schmidt and Winston's help, Cece attempts to get her new modeling agency off the ground (and out of the loft), but is discouraged when her first client is inspired to change career paths. Meanwhile, Reagan puts off reading Nick's new novel.