On New Girl Season 4 Episode 15, Nick is still broken up about his recent breakup with his girlfriend Kai and so he comes up with the ultimate pub crawl which will take place on Valentine's Day. He makes sure all of his friends will also take part in the crawl and tells them they will go to six bars in five hours and when they go to the last bar it will complete his map of a smiley face.
Winston takes on the job of designated buddy and has a backpack filled to the brim with provisions he thinks they made need throughout the night including nuts, books, water etc...At the bars Nick is acting fun and jovial and he even gets more people to join his pub crawl as he goes to different bars in the area. At the final bar, Nick doesn't want to go in because he finally doesn't want the pub crawl to end and expresses his feelings about not having anything to look forward to now that it is over. Thankfully his friends rally around him and encourage him about him having things to do in his life.
Meanwhile, Ryan is looking for a new job and in the process he also asks Jess to move in with him. At first Jess pretends like she did not hear what he asked, but after getting advice from Cece she decides to take the plunge and agree to move in with him. When they are celebrating back at the loft Ryan gets a message about getting the headmaster job at one of his favorite schools which will take him over 5000 miles away. They decide to see if they can make it work and agree to stay together despite being so far apart.