5 Times We Felt Sorry For Winston (& 5 Times We Hated Him)

5 Times We Felt Sorry For Winston (& 5 Times We Hated Him)

In New Girl, Winston Bishop moves back into the loft with Schmidt, Nick, and newcomer Jess in the second episode of season one after Coach moves out. Winston has just returned to the states after playing professional basketball overseas in Latvia. Winston is known for his kind and quirky personality and his willingness to always help a roommate in need.

Winston also loves cats and collard shirts with birds on them. One thing about Winston that seems to annoy everyone, including his audience, is his love of pranks and his inability to pull off a decent prank. Winston tends to go too big or too small when it comes to practical jokes and it never ends well. This, and other things, are the reason Winston walks a fine line between love and hate.

Sorry: His Job At The Radio Station

5 Times We Felt Sorry For Winston (& 5 Times We Hated Him)

When Winston gets back from Latvia, he doesn’t know what he’s going to do for work. He seems a little lost at first and struggles to figure out what direction he wants his life to go, for quite a few seasons. At one point, Winston gets a job at a radio station assisting one of his idols, sports announcer Joe Napoli. Winston’s dream job quickly becomes a nightmare when he realizes his idol is a monster. Watching Winston endure abuse in his workplace definitely makes fans feel bad for him.

Hated: Asks For A New Partner

Winston in police uniform with Aly on New Girl

Eventually, Winston finds his calling as a police officer for the Los Angeles Police Department. Once on the force, he is assigned a partner, Aly. Winston finds himself falling for his co-worker and partner and makes every attempt to shut his feelings down because he knows she has a boyfriend. Aly won’t stop talking about her relationship and it’s driving Winston crazy, but instead of telling her how he feels, he asks for a new partner, which embarrasses Aly and makes Winston look like a jerk.

Sorry: His Fellow Cops Make Fun Of Him

Coach, Nick, and Kai congratulate Winston after he graduates from the police academy in New Girl

Things are not easy for Winston on the police force. His fellow cops are mean and tend to bully him. Winston really struggles to find his friends and his place at work.

It’s hard to watch because fans know Winston’s heart and what a great guy he is, but his new colleagues can’t seem to see past his goofy first impression and his quirky side. It takes some time, but once Winston does eventually gain the respect of his fellow officers.

Hated: Sexual To-Do List

Winston smiling in New Girl.

New Girl didn’t end very long ago, yet there is a lot about the series that hasn’t aged well in the few years it has been off the air. The boys in the loft tend to overly sexualize the women they meet and viewers get a glimpse of their less-than-gentlemanly behavior in almost every episode. In one episode in particular, Winston casually mentions that he keeps a “sexual to-do list”. This fact is glossed over pretty quickly which leaves fans with a few questions.

Sorry: Gets Stuck In A Jacket

Ferguson on Winston's lap in New Girl

In one of the hottest, temperature-wise, episodes of the series, Reagan caves and buys an air conditioner for her bedroom. The roommates gather in her room to enjoy the cool temperature as Los Angeles reaches record highs that day.

The room gets so cold, the friends decide to put on some winter jackets they find in Jess’s closet. The jacket Winston chooses is a little snug and the zipper breaks, trapping him in the jacket. When the air conditioner stops working suddenly, Winston starts to panic.

Hated: Pranking Cece’s Wedding

new girl winston nick schmidt

Cece is about to marry Shivrang and as a wedding present, Winston decides to prank the happy couple at their wedding. The problem with Winston is that he thinks he knows how to deliver a good prank, but he doesn’t. Most of his pranks are either too big or too small. In this case, Winston’s prank is way too big and causes all of his roommates to find themselves in the vent above the wedding venue looking for a badger Winston has let loose.

Sorry: When He Needs Girl Advice

Winston does not have a way with the ladies and relies heavily on his friends for relationship advice. The friend he turns to most is Jess. Winston is in need of some serious girl advice in one episode, but Jess is nowhere to be found because she has been sequestered for a month on jury duty.

Winston panics and Cece offers to help, but ultimately, Cece is not Jess and ends up giving Winston the wrong advice, causing his latest love interest to end things with him and break his already fragile heart.

Hated: Gives Bad Advice

As bad as Winston is at getting advice, he’s equally bad at giving it. Winston tries to help Schmidt talk to Cece about an audition she is bailing on. Winston thinks Schmidt needs to give his fiancee a little tough love because she’s clearly talking herself out of a good opportunity out of fear. Unfortunately, Winston doesn’t really know what Cece needs and when Schmidt follows Winston’s advice it causes a huge fight between a fan-favorite couple.

Sorry: Naked At Cece And Schmidt’s Wedding

Winston is trying to change his ways and vows not to pull any pranks at Cece and Schmidt’s wedding, no matter how hard Coach begs him. Eventually, Winston is forced to pull a prank in an attempt to stall the ceremony because Schmidt is stuck on a plane and can’t get to the venue. Eventually, the prank is called off and Winston is left naked in a port-a-potty with no other option than to wear a curtain for the rest of the ceremony and the reception.

Hated: Pranks Cece And Schmidt’s Honeymoon

Winston may not have gotten away with a prank at the wedding, but he makes up for it by following Schmidt and Cece on their honeymoon and popping up from beneath the sand as the newlyweds try to relax under the sun. Another example of Winston not thinking his pranks through because now he’s stuck on Cece and Schmidt’s honeymoon, ensuring that the couple don’t really get to enjoy any one-on-one time.