Early life
Junior high
Little is known about Ramona's life before seventh grade, where she met Matthew Patel. She and Patel dated for only a week and a half, during which Ramona pretty much used Matthew and his mystical powers to ward off flocks of jocks interested in her. She dated Matthew, according to her own story, because he was the only non-white and non-jock kid at her school. The two only kissed once, and it ended shortly after due to Matthew's pre-adolescent capriciousness. Afterward, Patel moved far away.
High school
It is unknown what she was doing in eighth grade, but in her freshman year she was stalked by Lucas Lee, who had a crush on her and continually asked her out. Eventually, Flowers relented and the two dated for a long time. According to her, all they did was sit on a curb and smoke. At some point in the relationship Flowers cheated on and left him for the "first cocky pretty boy" that came by, Todd Ingram.
Ramona dated Todd for the remainder of high school, saying they were the "bad kids" together. He vanished for two weeks while they dated, during which he went vegan (having apparently been studied by scientists). Todd returned and took Ramona out of class to prove his love for her by blasting one of the two craters in the moon, causing what Ramona described as "About 30 pages of explosions and tidal waves". She placed her hand over her mouth in utter shock.
University of Carolina in the Sky
Todd ended up going to a vegan college while Ramona went to the The University of Carolina in the Sky, though, so the two decided to let each other go.
During her time in college, Ramona's roommate was Roxie Richter, who turned out to be a lesbian. Ramona became very curious about what it would be like to be intimate with a girl, and as Richter was presumably already attracted to her, they began dating. It is implied that they had sex, embarrassing Ramona. After post-secondary, they broke up and hadn't seen or heard much from one another. Ramona would later claim the relationship was "just a phase".
Aftermath
At some point after breaking up with Roxie, Ramona dated the Katayanagi Twins, Kyle and Ken, but without each knowing about the other (basically cheating on both of them). When the truth was revealed, they dumped her, but the three of them developed no sense of hostility between each other.
Eventually, Ramona went to a party and met Gideon Graves there and quickly developed tender feelings for him. Despite Ramona's feelings for Gideon, Gideon saw his relationship with Ramona purely as an experiment, during which he inflicted Ramona with The Glow. Fed up with him constantly pushing her away, Ramona decided to leave Gideon, leaving nothing except a letter. Unfortunately for Ramona, Gideon walked in on her just as she finished the letter. Ramona, filled with intense emotions, became overwhelmed by The Glow and vanished into Subspace, taking the letter with her.
Dating Scott Pilgrim
Arrival in Toronto
Traveling through the wormhole, Ramona arrived in Toronto, Canada, where she found a job as a "Ninja delivery girl" for Amazon.ca. She also got a cat, which she named Gideon as a way of working out her affairs. Shortly afterwards, she went to a party, where she met Scott Pilgrim, who annoyed her by talking about Pac-Man. When delivering packages to houses, she realized Scott had ordered something just so he could hit on her, and she reluctantly agreed to date him, having never experienced a relationship with anyone who was pure at heart. Their relationship has their ups and downs like any. She remains enigmatic and Scott remains a dork, but it's that very interest that keeps the two together.
During Julie's early birthday party, taking place before Volume 4, she tells Scott that he is the nicest boy she has ever dated. This moment of happiness began to falter in Volume 5 when she learns from Knives that Scott had cheated on them both. She dismissed this bit of news at first, but after Scott accidentally blurts out that he cheated on Knives with her, she became increasingly upset, not only calling him a bad person, but "another Evil Ex waiting to happen," although she cheated on many of her boyfriends herself.
Feeling guilty for her own past actions, Ramona confessed that she was no better. After hearing some encouraging words from Scott, she thanks him before vanishing, making Scott think it's over until Volume 6.
Defeating Gideon Graves
Meeting up with Scott in Subspace after his initial defeat against Gideon Graves, she apologizes and helps him fight Gideon. After being wounded by Gideon, she becomes trapped in her own mind and her desires controlled by him. After breaking free thanks to Scott, she takes control of her mind once more to cast Gideon out, leading to one last fight in reality. In the aftermath of their victory, she explains to Scott she feels like she has to keep running or else she feels "stuck." She's scared of the prospects of not changing but wants to be with Scott who continues to support her.
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