Of all the shows in the Arrowverse, Supergirl is probably the most optimistic, which is why it has some of the best friendships to go along with it. The sisterly bond between Alex and Kara Danvers is nothing short of perfection, perhaps only trumped by the friendship between Kara and Winn Schott.
Kara and Winn have been friends since before the show even began, with Winn providing a warm and welcoming face for Kara when she first started working for CatCo as Cat Grant's assistant. However, these two have faced some challenges in their friendship.
10 Winn Used To Have A Crush On Kara
One of the biggest ways to ruin a perfectly good friendship is for one friend to develop an unrequited crush on the other. From Supergirl's very first episode, it was obvious that Winn liked Kara, even before she came out to him as Supergirl.
What followed was an exhausting and painful to watch series of events, with Winn staring longingly at Kara from the sidelines. Eventually, he mustered the courage to tell her how he felt, which turned out to be a big mistake. Winn almost ruined his friendship with Kara because he thought he loved her.
9 Winn's Dad Was A Serial Killer
In the first season of Supergirl, not much was known about Winn, other than that he was deeply in love with his best friend who didn't love him back. However, midway through season 1 it was revealed that Winn was the son of the villain known as Toyman.
Toyman used to make toys for young children until he was betrayed and used by his former boss. He was so enraged by this act that he built a bomb and used it to kill innocent people. Kara is known for seeing the good in everyone, but the fact that her friend's dad was a murderer must have put a damper on her friendship.
8 Kara Rejected Winn
Although it's definitely not Kara's fault that Winn had feelings for her, nor was it her fault that she couldn't return them back, she probably could have handled the situation a little better. Winn had been feeling this way for a long time, and on some level, Kara surely must have known.
During the whole debacle with his father, Winn was in a very bad place emotionally. His father was out of jail and on a mission to kill more innocent people. Upset, Winn made a move on Kara, only for her to reject his advances. Humiliated, Winn took some time away from their friendship.
7 Winn Helped James Against Kara's Wishes
In the second season of Supergirl, Winn, and especially James Olsen, were growing disillusioned with forever being sat on the sidelines while Kara went out on a daily basis to fight evil aliens and risk her life for the sake of others.
Therefore, James came up with the idea of becoming a crime fighting vigilante called Guardian. However, he needed support so he asked Winn, who agreed. After a few false starts, the two became quite formidable. However, when Kara found out, she was shocked, worried, and upset that they hadn't told her.
6 Winn Didn't Believe Lena Was Innocent
For one of the best characters to appear on the show, Lena Luthor hasn't exactly had the easiest time of it lately. Even in her debut season, Lena still had to fight off the stigma of being a Luthor, even though she had no desire to harm Supergirl or her cousin.
However, when her mother, Lillian, escaped her trial, Lena was automatically blamed and arrested. Things only got worse when Lillian broke her out, making Lena look even more guilty. Kara was the only one who believed in Lena, and even Winn found it difficult to accept that Lena was innocent.
5 Kara Told Winn She Was Supergirl
When Kara told Winn that she was Supergirl after she had saved a plane full of civilians from crashing, it was quite a surprising turn of events, not least for the viewers. A lot of heroes keep their secret identity hidden from their loved ones.
Kara told Winn on her very first day as Supergirl, and Winn even made her costume for her. While this could be seen as a good thing, the reason why heroes don't tell their friends and family about who they are is because the people closest to them often end up hurt, or worse, dead.
4 Winn Left Kara To Go To The Future
Supergirl had to go up against a very scary, very extreme threat in her third season. Reign was a Worldkiller designed to level planets and she had no mercy. She even almost killed Kara at one point.
Kara needed help, and so Mon-El brought with him the Legion, a superhero group from the future. When Reign was finally defeated, the Legion returned to their own time and Winn decided to go with them. It was the right thing to do, but it meant Kara and Winn couldn't even message each other for nearly two years.
3 Winn Designed Kara's "Draft" Superhero Suits
As well as being incredibly clever when it came to hacking and inventing new weapons for the D.E.O., Winn was also surprisingly adept at designing costumes for the various superheroes he met over the years. His first superhero suit he designed, though, was for Kara.
While the finished version looked absolutely phenomenal, there were some other designs that Kara rightly vetoed. Winn is by no means a chauvinist, but his first drafts were incredibly revealing, something that probably wouldn't have happened if Kara was a man.
2 Winn Dated Siobhan Smythe
For the duration of Supergirl's first season, Kara was mentored by media mogul, Cat Grant. Cat had a sharp tongue and an even sharper temper, but she did genuinely care about Kara, which is why she was hurt when Kara broke up with her son.
Out of pettiness, Cat hired another assistant, Siobhan Smythe, who went out of her way to make Kara look incompetent and unprofessional. Despite how awfully Siobhan treated his best friend, Winn still dated Siobhan for a few weeks.
1 Kara Refused To Let James And Winn Fight Crime
When Kara finally found out about James and Winn's antics fighting crime as Guardian, she was not best pleased at all. While her reaction was understandable as she was worried about her best friends getting hurt or killed, she did cross the line somewhat.
Winn was incredibly supportive when Kara came out to him as Supergirl, and did everything he could to make her life easier. It's a shame that she took so long to do the same for him, even telling him that she couldn't support what he and James were doing.
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