Jess helps Schmidt and Nick pitch their new business venture - the "Swuit," a suit made entirely of sweatshirt material - to entrepreneur Lori Greiner. Meanwhile, Winston and Coach decide they will invest in Cece's future.

After being emasculated in front of Cece, Schmidt insists on a manly bachelor party weekend in Vegas, but the road trip goes awry when the guys end up at a desert biker bar and he must put his newfound bravado to the test.

After Jess announces that she is ready to date again, Schmidt pushes her to give her workout partner, Robby, a fighting chance. Then, when Cece hires a hunky new bartender, Nick struggles to understand male beauty, while Winston's newfound confidence makes him irresistible.

When Jess gets nervous about starting her new position as principal, Nick and Schmidt decide to take her on a relaxing day trip to Solvang, which quickly goes "sideways." Meanwhile, with Cece's help, Winston tries to finalize his divorce from Rhonda, but finds that he and Aly are caught in a series of never-ending pranks.

The gang gathers for a one-year memorial service for a beloved friend. Meanwhile, Jess discovers Coach owes Nick a large sum of money.