Winston is one of the most lovable characters in New Girl. This is due to his heart of gold and how he’s always there to support the rest of the group. His progression as a character is also one that is particularly interesting, as he changes rather significantly from the beginning of the show. He goes from being a bit of a normal character to somebody who is extremely weird.
This massive change in his character ultimately would be the spark that the show needed to strengthen its core. In fact, Winston by far has the weirdest moments from the group in the entire series. In fact, these specific instances are among the most popular from New Girl, so they clearly work.
10 When He Has A Date With Furguson
When Winston originally meets Furguson, he plans to kill him as revenge on Daisy for cheating on him. However, he later changes his mind and instead steals him from her. From there, the pair would be inseparable.
However, the connection is a bit strange at times on Winston’s end. The prime example of this is when he sings to Furguson saying that he is going to make him pasta, while also talking to him like a human. It seems as though it is actually a date, too.
9 When He Sings “Groove Is In The Heart”
During a night at the bar, Winston certainly is having himself quite the time. He is drinking a good amount, which in turn, leads him to be very excited and happy. However, he becomes extremely strange in the process.
While alone, he begins to sing “Groove Is In The Heart” in a loud and high-pitched tone. Although the others around him are feeling a bit uncomfortable by this, he is enjoying his moment in the spotlight and dancing around,
8 When He Lies About His Identity To Help Nick
Nick finds himself in a lot of trouble as the two women he is dating both end up at the loft at the same time. This leads to them fighting, while also being understandably angry with Nick, too.
Winston is on the night shift, so he is desperate for sleep. As a result of this, he gets the conflict to stop by pretending he is Nick’s romantic partner, Theodore K. Mullins. It is particularly weird, but also hilarious in the moment, as he uses an extremely deep and powerful voice.
7 When He Bonds With Dunston
Winston has deep feelings for Aly, but at this point of the series, she is in a relationship. Thus, the pain of this becomes too much for Winston to handle, so he decides to get a new work partner in Dunston.
When the two meet, there is instant chemistry, as they bond over loving the same CD. This is where they sing Track 7 on it, “Elation” while being at the bar. It is comical because they both get so into it, while also dancing in a goofy manner.
6 When He Pranks Cece’s Wedding
When Schmidt asks the guys to help him sabotage Cece’s wedding, Winston immediately jumps on board. This is solely because of the fact that he enjoys pranks way too much. Also, when it comes to pranking the wedding, he takes it too far by putting a wild badger in the air vents.
There is truly no reason for him to do something so extreme, but alas, this is typical Winston behavior. Also, before this part, he also asks a bit off when he plays “Cotton Eyed Joe” on the speakers and refuses to turn it off.
5 When He’s Oddly Okay With Rhonda’s Prank On Him
Speaking of pranks, Winston ends up becoming involved with Rhonda because of her love for them, too. The two briefly date, but end things when she is forced to go on duty suddenly.
However, when she returns, she has a baby and tells Winston that he is the father. This leads to him telling the baby that he will never leave him, as he is not like his own father. However, Rhonda then says it is a prank. Instead of being livid, like most people would, Winston screams that it is amazing that she pranked him with a baby.
4 When He Keeps Swallowing Gator Teeth
Jess is in a particularly rough spot, as she still has deep feelings for Nick, but he is now with Reagan. She decides to open up to Winston about this and tells him that she feels that she cannot even knock on his door. Winston then offers emotional support and does it for her.
It is such a kind gesture on Winston’s end, but it of course turns weird. To break the ice, Winston asks Nick to have another gator tooth because he swallowed it. Nick then says it is the last one because this keeps happening, and Winston immediately puts it in his mouth.
3 When He Gives Sam A Bird Shirt
Winston is a very kind soul, and this is certainly the case when he decides to give Sam a bird shirt entirely out of the blue. Sam does not put it on, though, as he does not want to change in front of everyone at the bar.
However, it becomes quite strange with the way Winston reacts to this. He slowly backs away and intensely stares at Sam, as a way to tell him that he is watching him. It is just a weird way to handle a situation like this, but again, it is right in line for Winston.
2 When He Starts Puzzling
Puzzling is certainly a fun hobby to partake in, but Winston may not be the best fit for it. This is due to the fact that he not only struggles with them but becomes noticeably intense while trying to complete them.
In fact, he progressively becomes angrier with Schmidt, as he keeps trying to steer him to stop. He also continues to talk to himself while doing them and even uses an almond as a piece to try to finish it.
1 When He Sings “Defying Gravity”
In the first season of the series, Winston is actually one of the most traditionally normal characters in the group. However, when he is driving to Mexico to see Shelby, the audience is given a real first look at how strange Winston can be.
While driving, he is singing “Defying Gravity” from the musical, Wicked. That is not weird by itself, but it becomes that way when he tries to sing exactly like the singer of the song. It leads to him singing in an extremely high-pitched voice, while also being quite dramatic with his mannerisms, too.
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