Winston Bishop is a lovable fan-favorite from New Girl who is typically a carefree and quirky character who leads a great and happy life on the well-received show. Winston appeared after the pilot episode of the series and went through a great arc of changes from beginning to end while being hilarious along throughout.
Although he’s an optimistic and hilarious character, Winston still has sad moments about his character and sad things that have happened in his life and backstory on the show.
Having To Quit Basketball After An Injury
Although Winston was never a very successful player as he was usually on the bench in Latvia when he was playing abroad, it was still sad that he had to quit after being injured.
Even though he moved back in and ended up joining the show because of this plotline it’s still sad to think about Winston having to quit basketball over an embarrassing injury.
Difficult Time Adjusting After Latvia
Winston had to quit being a professional basketball player in Latvia after an injury and he moved back into the loft with his friends Nick and Schmidt and new roommate Jess.
He returns to the states without an idea of what he wants to pursue next and jumps from job to job as he finds it difficult adjusting to life after being an athlete. He has a string of terrible jobs as he tries to find his footing careerwise, which is relatable but also upsetting and sad.
His Beginnings As A Police Officer
When Winston first started to show interest in joining the police force he’s met with a lot of resistance from his best friend roommates who all believe he’s too immature and not responsible enough to ever succeed in that profession.
Winston proves them all wrong by successfully becoming an officer after passing his exams only to have a difficult time adjusting to his new co-workers at the beginning.
He Is Afraid Of The Dark
Winston reveals that he’s terrified of the dark when he’s stranded at night in the desert in the Season 1 finale. He spends the entire episode in fear and the gang doesn’t seem to care about his fear or really try to help him through it.
Poor Winston never really overcomes this fear throughout the series and it seems that he’ll always be afraid of the dark and being stranded at night probably didn’t help things.
He Had Difficult Relationships
Although most of the New Girl main cast of characters has a difficult time dating, Winston had a particularly difficult time with significant others throughout the series.
There was Daisy who was a potential love interest but revealed she was already involved with someone else. There was also Rhonda who brought out his insane pranking side and the two married each other, officially, as a prank. Though Winston finally met his wife Ali and the two were happily married by the end, he still had a sad and difficult dating history.
Allergic To MSG
Winston has a terrible allergy to MSG that causes lockjaw when he eats any food that contains MSG and unfortunately he does in the show. Jess uses his pain to get upset with the restaurant who has been printing out too many menus and putting them at their door.
She goes to the restaurant with Winston in tow and yells at the owner to stop printing out all the menus or she’ll show everyone Winston and tell them that’s what happens when you eat the food there, which may have been inconsiderate of both him and the restaurant.
Left Out By Schmidt And Nick At Times
It’s always difficult being the third wheel in a friendship and unfortunately this happens to Winston as Nick and Schmidt are so incredibly close.
It’s even sadder since Nick and Winston grew up together in Chicago and Nick didn’t meet Schmidt until college but despite this, he is sometimes left out.
Realizes He Didn’t Know The Whole Story About Losing His Virginity
In an episode where the gang all reveal how they lost their virginities, Winston begins to tell his story and Nick is worried that he might not realize that he lost his virginity to a woman who was a prostitute that Nick’s dad solicited.
Nick realized it at the moment and wasn’t comfortable having sex, but Winston never fully realized it until Nick broke the news to him after he told his story.
He Gets Injured Very Easily
From his basketball injury to his wedding-themed pranks to just randomly hurting himself throughout the show it’s a sad fact of Winston’s life that he gets injured very easily.
Although he does find success as a police officer by the end of the show, the fact that he continually gets injured at random moments does affect his life especially after he had to quit playing basketball.
Took His Ex-Girlfriend’s Cat
Although Winston and Ferguson the cat’s special bond is an adorable relationship it’s pretty sad that Winston took the cat from his ex-girlfriend in the first place. Winston changed throughout the series and one of his best relationships was with his cat Ferguson.
Even though they become great friends and it became an ongoing joke for Winston and they had a lot of fun with his feline bestie, it’s still a little sad that he took the cat away from an ex and had to have this fact mar the otherwise wholesome relationship.
