Winston became quite the fan favorite as New Girl continued, as he developed into a truly hilarious character. This was due to the fact that they upped his strangeness, which ultimately made him a far better fit with the rest of the group. Also, he was clearly quite a lovable character because of how sweet he was to the people around him. The show would give him a great ending with Aly, but there were certainly hardships along the way.

Winston would face a ton of obstacles throughout the show’s run, but it ultimately would enhance his likability as a character. Rooting for him was not challenging for audience members because of how sweet he would remain as it transpired. His progression was easily one of the best among the main characters, as he bounced back from every negative moment that came his way. However, that does not mean that they were not still hard to see as fans of him.

10 Caught Schmidt And Cece In His Car

Winston was the first one to find about Schmidt and Cece, as he caught them in his trunk while at the Mexican border. This was very challenging for him, as at that point in time, he was interested in Cece and could not understand why she chose Schmidt.

At this point of the series, Schmidt was at his ultimate worst with his personality. Therefore, it was very tough for Winston to accept it. This all happened in his very own car as well, so it was an awful experience all around for him.

9 His Father Abandoned Him

Winston grew up not knowing who his father was, and it impacted him immensely. He often stated how much it hurt him, and he even latched on to Nick’s dad in an attempt to feel like he had one of his own.

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This also would change his relationship with his mother, as he often felt that he had to take care of her. Overall, growing up without a father was one of the most heartbreaking storylines for Winston, as it was clear that he badly wanted to meet him.

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8 Had Nervous Breakdown In Desert

While Nick was planning to move into Caroline’s, he freaked out and drove to a desert. He then threw his keys, which petrified Winston because of his fear of wolves. Jess then did the same after originally coming there to bring them back to the loft, as Nick said he was indeed going to Caroline’s after all.

Winston freaked out immensely from there and although it was funny, it also was hard not to feel bad for him. It would impact his entire night, as it was apparent that he was genuinely petrified with the situation at hand.

7 Got Cheated On By Daisy

During their first few interactions together, it seemed as though that Daisy very well could have been the one for Winston. She helped him find his confidence with women again, but sadly, things would then take a turn for the worst.

Daisy cheated on Winston as soon as their relationship started, as she had a man in her shower while she accepted Winston’s question. He would later confront her and she came clean. Thankfully, Winston left her immediately after.

6 Also Got Cheated On By KC

Winston’s relationship with KC was certainly short, but the impact of it was very negative on him. This was due to the fact that she also would cheat on him. Instead of being honest with him, he found out in a rather peculiar way.

Cece went over to her place to tell her that Winston had died. KC was upset by the news and the man she was cheating on Winston with would comfort her. This led to Winston scaring her by jumping out and naturally, fans would never see KC again.

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5 Coach Was Cold To Him Before He Left

When Coach was moving out of the loft, he used the clean break method, as he said it would make leaving easier. However, this would impact Winston significantly, as he felt as if coach was just aiming to forget him.

Winston brought up memories to him, specifically with the crepe pan they bought together. Although Coach and him would have a touching moment at the end of the episode over it, there is no question that Winston was hurt deeply by Coach’s coldness.

4 Got Pranked With A Baby

When Rhonda came back unannounced, she tricked Winston into thinking that she had his baby. Winston delivered a heartfelt speech about how he would be there for him, unlike his own father. However, Rhonda then dropped the news that it was a prank.

Although Winston would say that it was amazing, it still was a rather sad moment for it not to be real. Winston showed that he was willing to accept that child, even though it was a complete and utter lie.

3 Was Partners With Aly While She Had Boyfriend

Winston began to develop feelings for Aly while working with her as cops. However, she did not feel the same at first, as she had her own boyfriend. It ended up making Winston so uncomfortable that he temporarily chose to not work with her.

It was extremely challenging for Winston to hear Aly talk about her boyfriend so often. Although he would eventually date her, the road there was immensely hard on Winston.

2 Was Overwhelmed After Seeing Color For First Time

As the series progressed, it became known that Winston was colorblind. This was the reason why he had a lot of trouble when it came to solving puzzles. Aly, however, would end up getting him colorblind glasses to allow him to see colors for the first time.

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A touching moment would soon turn sour, as he ultimately became quite overwhelmed by the many different colors around him. In fact, he would particularly hate the color blue, as it would be what really triggered his panic attack.

1 Ferguson’s Death

The worst thing that happened to Winston was Ferguson’s death. Ferguson was his best friend, as evidenced by the amount of time he spent and talked with him. However, during the final season, it was revealed that Ferguson suffered a fatal heart attack.

It was truly devastating, as even though Winston held it together for a whole year, he finally broke down over losing his furry friend. Thankfully though, he would find a new kitten in the bar to bring home, but there was no way to truly replace Ferguson.

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