In Jess & Julia Winston reconnects with a former 'booty call', Shelby, who he later starts dating. Winston enjoyed the analytical aspect of Schmidt's job but also realized that he would not want to be behind a desk, to which Cece suggests that he should consider a career in criminal justice. Although Schmidt doesn’t think Winston would be any good in marketing he agrees to let Winston shadow him to see what he does as a marketing analyst. Again unemployed, Winston asks Schmidt for help with his career search. Following this epiphany he quits his radio job in spectacular fashion. When Jess has twenty minutes to decide if she should give-up teaching and take a new job, Winston attempts to illustrate the importance of making decisions, only to realize that he has never made a true decision in regards to his own career. He eventually moves up to be producer of his own talk show from 2:35 to 5:35 a.m. In Normal he decides to quit his job as Elvin's caretaker and lands a position as an assistant for the bombastic sports radio host Joe Napoli at KQTO 87.4 FM. He lands a temp job in Bells, but is quickly fired when he wastes mailing supplies in practicing "Eye of the Tiger." He gets a job as a part-time nanny for Schmidt's boss who has a son, Elvin. He also has no experience, and cannot make a complete resume (skills in basketball, and love for ducks, which isn't even true). He gives himself a crash course on the internet, watching countless youtube videos, and movies. He quickly realizes he struggles with small talk in interviews as he has not been keeping up with current events for the last 2 years. Winston later begins adjusting back to life in the US, and the first things he does is look for a job. Winston won the large room back by pulling some reverse psychology on Schmidt by suggesting he keep the big room. This offended Schmidt because he felt like it was all a joke, but they later reconciled and earned each other's respect. He managed to manipulate Schmidt in switching rooms by claiming Schmidt is the new 'top dog'. Winston used to occupy the largest room in the loft, which Schmidt took when he left. Winston later helps Jess get her stuff back from Spencer, and when Spencer doesn't offer up Jess' jam shirt Winston joins the guys by putting on one of her hats (they do this to dare Spencer to take the hats off of them). The new roommate relationship gets off to an even rockier start when Jess breaks the TV with a basketball. Jess makes him breakfast the next morning and not having met him before, she introduces herself by singing while he is massively hungover. On Winston's first night back at the loft, he goes out with Nick and Schmidt for some drinks and gets wasted. In Clavado En Un Bar, it is revealed that Winston was the 9th guy on the bench for the 8th best team in Latvia and after being traded to the Kraslava City outdoor league suffered a humiliating leg injury that ended his basketball career. Being a former roommate who returned shortly after Coach left, Winston finally comes back from playing basketball in Latvia, completely unaware of anything that has happened in the US for the past two years.
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