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Headscratchers Main Webcomic YMMV main index Narrative
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Tipper O'Donnell The main character, twelve-year-old tomboy Tipper Namir, whose coming of age, and later, adult life, is the focus of the strip.
Snickers Namir Tipper's older sister. With their father having left at a young age and their mother chronically unreliable and eventually also gone, she was the main authority figure in the strip's early years, even though she was fifteen at the start.
Blue Deiter One of Snickers's two best friends in high school despite being a year older.
Joy Satu Snickers's other best friend, who mostly hangs around Blue.Charles "Chachi" O'Donnell Introduced as the sadistic TA of one of Tipper's courses who seems mildly turned on after she tells him off in front of the class for giving her an impossible assignment. It's soon revealed he's Gabby's cousin, and when she sees the chemistry between them, she pushes them together. They eventually marry.Twix Namir Early on, Bob set Snickers up with his cousin, Twix Dorpe, nothing like his family (of idiotic slugs) in appearance or personality. They hit it off immediately, and impulsively married on a bender soon after. Since then, he's been something of a father figure to Tipper.
Gabby Ramos Formed a rivalry with fellow art student Cedric in high school; when Cedric began trying to win Tipper's affections going into junior year, so (platonically) did she, introducing her to the strip. She soon realizes that she wants to be more than friends with Tipper, and pretends she already is to her internet contact Falco... who, it turns out, goes to the same high school. When Falco talks to Tipper for the first time, it's under that assumption, and once Tipper tells her that she's not into girls and doesn't believe Gabby is, Falco starts pushing the two of them together, which ends with the two of them not speaking for some time. Things settle down between them after a while, and when Gabby needs a roommate and Tipper needs a place to live, they start sharing an apartment, which as of 2011 they still share, along with their respective lovers.
Joan Cutter A childhood friend of Gabby and Cedric who returns to town, and Gabby realizes she still has feelings for her. A bit later, when she's considering moving in with her Bastard Boyfriend for security, she jokes that maybe she should marry Gabby instead; when Gabby makes it clear Joan has hit a nerve, Joan offers to date her for real, despite the fact that Tipper and Charles kind of hate her.
Cedric van Helgen A customer at a comic shop where Tipper filled in for a friend for a bit in the fall of '02, he immediately fell in love with her and became something of a stalker, which she tolerated because he was a close friend of her real love interest at the time, Taimoor. She finally agreed to date him in early '04 when the two of them were Locked in a Room in a fire drill, but they broke up toward the end of the schoolyear when he realized she still felt more strongly about Taimoor. Because of Taimoor and Gabby, they remained friends; when it was revealed that Falco went to the same high school as the main characters, she started to date him, and they've been in an on-again/off-again relationship ever since.
Jennifer "Falco" Anneston An internet contact of Gabby's, she meets the main cast in person in early '05, and begins dating Cedric. Despite break of several months in '07-'08 after about a year long-distance, during which she dated Isaac, the two remain together as of 2011, and she has a child on the way.
Roxanne Huss-Deiter Blue's biological sister, who raised her after she ran away from their alcohol, neglectful mother. When Blue's more or less on her own, her boyfriend Dmitri gets her pregnant and runs, returning when the child is born. She forgives him surprisingly easily.
Isaac Telford Comes into Blue's bar on her shift and repeatedly asks for water so he won't be carded; Blue's afraid of him until he reveals that he suspects (correctly) that they share the same mother, and that's why he's following her. After this, he starts dating Falco while she's on the outs with Cedric, but that doesn't last, so he then moves on to Joy, but after saving the relationship from Joy's accusation that it's built on lies, leaves her for the same reason when Blue reveals that the reason she's been so distant is that she's hiding a miscarried pregnancy.
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