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On New Girl Season 4 Episode 16, Jess and her friends are planning a trip to Portland to go to her father's wedding. While packing she informs her friend she hasn't talked to Ryan in a week, but she expects him to be at the wedding on time. When they arrive in Portland Jess gets a call from Ryan and he tells her he is unable to make it out there because he has to be back at work the next day and wouldn't be able to make a quick enough flight. Jess gets depressed, but thankfully Nick and her friends are there to pick up the pieces and they decide to go on a tour of Portland which Jess had set up.

While on the tour Jess shows them different places she went to as a child and she gets to the final stop, which is her house, Jess's mom Joan has a huge banner up welcoming Ryan to her home. When Jess tells Joan about Ryan cancelling she starts to get emotional and runs up to her room. While in her room Nick goes up and talks to her and tells her what Ryan is doing sucks and he shouldn't do this to her because it's not right. At first Jess is reluctant to take Nick's advice, but in the end she decides he is right and Ryan should have made some time for her. Jess ends up breaking up with Ryan over voicemail after her father's wedding.

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