Felicity Smoak was one of the most popular characters on Arrow. She made her Arrowverse debut in the third episode of Season 1, and she formed an instant connection with Oliver Queen. Over time, Felicity became a true member of Team Arrow and helped the gang take down criminals for seven seasons.
Despite being an original member of Team Arrow, though, Felicity did have a dark side. It wasn't as pronounced as Oliver's but it still caused the team several issues. Felicity's poor decision making also affected her personal life, and sometimes, it lead to the people she loved getting hurt.
10 Aligning Herself With Helix
Felicity's backstory was surprisingly dark for such a cheerful and quirky character, but it did explain a lot, especially when Felicity started going rogue. In Season 5, John Diggle had been wrongfully imprisoned and the team were at a loss about what to do.
Felicity's hacking skills on their own were not enough to free Diggle, so she asked Helix, a group of hacktivists, for help. This resulted in Felicity turning down a very dark road, which involved blackmail, and even freeing a very dangerous prisoner.
9 Letting Her Son Believe She Was Dead
In Season 5, the flashbacks which were an iconic part of the show, finally ended as Oliver went back home to Starling City. During Season 6, the flashbacks were used to highlight the backstories of other characters, but in Season 7, this plot device was turned on its head.
Instead of flashbacks, viewers were introduced to flash-forwards. This narrative revealed the bleak future of Team Arrow, including Felicity. Here, she let her step-son, William, and her friends believe that she was dead, which wasn't very motherly of her.
8 Creating Archer
Season 7 was Felicity's last season on the show as a main character. Happily, though, this season still gave Felicity a lot to do. In the first half of the season, Felicity had to fend for herself against very dangerous enemies such as Ricardo Diaz.
After being attacked in her home several times, Felicity designed a security software called Archer which identified people entering via their DNA. However, in the future storyline, this program was stolen by the Ninth Circle and used by Galaxy One for their own means.
7 Turning Against Curtis And The Team
Season 6 was a delicate time for Team Arrow. While they started off strong, cracks began to develop shortly after Crisis On Earth X. The mysterious Vigilante was revealed to be Dinah's ex-boyfriend, and it transpired that Rene had sold out Oliver.
Naturally, Oliver was furious and refused to listen to their side of the story. Curtis sided with his teammates but Felicity was firmly on Oliver's side. Given how close Felicity and Curtis were, one would have expected Felicity to be more understanding.
6 Becoming A Vigilante
Technically, this is presented as extremely heroic within the show itself, and Felicity definitely helped to save a lot of lives. However, something that Arrow never glossed over is that vigilantes are technically illegal, so Felicity was operating outside the law.
Being a vigilante isn't only dangerous for the person taking down the criminals. Anyone close to you is at risk of being targeted, and even killed, by the very criminals you hunt down. By joining Oliver, Felicity put all her loved ones in danger.
5 Helping Free Cayden James
As previously mentioned, during Arrow's fifth season, Felicity made a bold and dangerous choice by allying herself with Helix. For the most part, it was fairly harmless (for a criminal organization, that is), until they asked her to break their leader out.
Cayden James was being held by ARGUS in a very secure facility and Felicity actually went against Team Arrow to free James. This had extreme consequences for the following season, as James became the main antagonist for the first half of the season.
4 Breaking Up With Oliver
Oliver and Felicity had a particularly tumultuous relationship, especially during the first few seasons of Arrow. They developed feelings for each other in Season 2, denied those feelings in Season 3, and finally got together in Season 4, before breaking up again.
The reason for their break up was that Felicity found out that Oliver had kept his son a secret from her. However, Oliver had to keep it a secret in order for him to be in his son's life. Felicity should have understood completely, instead of overreacting the way she did.
3 Hacking The Department Of Education
In the third season of the gritty superhero drama, a whole episode was dedicated to Felicity and how she became the person she was today. It was a great episode and really gave Felicity extra depth. It was also rather surprising in some aspects.
Firstly, it revealed that Felicity was a goth when she was at college. Secondly, Felicity and her then-boyfriend hacked the Department of Education, a maneuver as impressive as it was totally illegal. It was also really irresponsible and Felicity should have known better.
2 Her Treatment Of Her Mother
Felicity remained rather tight-lipped where her family was concerned for the first couple of seasons of Arrow. However, fans finally got to meet the woman who brought up Overwatch when Donna Smoak visited Felicity early on in Season 3.
Felicity was clearly pretty uncomfortable in her mother's presence, which seemed a bit odd. Sure, Donna was very flashy and loud, but it was clear that she cared about her daughter. Felicity just appeared to be ashamed of the woman who worked so hard to raise her right.
1 Piggybacking On Barry And Iris's Wedding
Barry Allen and Iris West's wedding had been planned since the end of Season 3 of The Flash. Iris in particular had worked tirelessly to make sure her wedding was as beautiful as she had dreamt it. It was even the focus of the 2017 crossover event.
Weddings should be about one thing: the bride and groom. Unfortunately, Barry and Iris's wedding was gatecrashed by Nazis so they were forced to improvise. Felicity decided then was a good time to declare her feelings for Oliver, which was hardly fair to Mr. and Mrs. Flash.
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