The official character page can be found here.
Introduced in issue 1, John is one of the comic's central characters, based primarily on the author and artist of the work. John is relaxed and easy-going with a self-deprecating sense of humor. He wishes for a girlfriend but is so overcome with anxiety at the thought of asking a woman out that he doesn't really bother.
- Abusive Parents: Mentioned off-handedly by Sam.
- All Men Are Perverts: John has to force himself not to stare at women's breasts when talking to them.
- Author Avatar: John Kossler is writing a webcomic about John Kossler writing a webcomic.
- Beware the Nice Ones: It's implied John headbutted Yorick in the face when he was drunk.
- Butt-Monkey: To Jason and Yorick.
- Carpet of Virility: John's chest and back.
- Chew Toy: See Butt-Monkey.
- Dogged Nice Guy.
- Gratuitous French: John revels in the fact that he speaks French and does so whenever possible.
- Raised Catholic.
- Shrinking Violet.
- Talking to Themself: John is one of many characters in the comic to do so.
- The Teetotaler: John didn't get drunk between the day he turned 21 and the events of Day One.
- The Corrupter: Yorick to John and Poor Trotmann.
- Deadpan Snarker: And how!
- The Imp: More so in the Dungeons and Dragons game than in the comic proper, but still fits the trope nicely.
- Jerkass: Um... YES.
- Monster Clown: His jester character in the D&D game.
- No Social Skills: He drinks the tears of a waiter who pisses him off.
- Pet the Dog: Yorick has a soft spot for stray kittens.
- Black Best Friend: Grace to Lillith, although she's come into her own since Day Two started.
- Characterization Marches On: Grace started out as merely a foil for Lillith, but has since gotten more character development than she.
- Does Not Like Men: More specifically, she doesn't want an immature man.
- Sassy Black Woman: Played with in that her sass seems to be a defense mechanism.
- Smoking Is Cool: Played straight when Lillith looked up to her as she was the only character who smoked cigarettes regularly, now subverted since it's been revealed she's just as vulnerable as the rest of the cast.
- Boisterous Bruiser.
- Catchphrase: Jason says "who cares?" or some variant thereof whenever asked about another character's emotional state.
- Cloud Cuckoolander: Jason lives in a world wherein everyone compliments him.
- The Corrupter: "Why bother cultivating this girl if you're not going to plow her?"
- He-Man Woman Hater: Played for laughs.
- Nerds Are Virgins: Subverted in that he has a girlfriend.
- Not Good with People: His antics help get him kicked out of a restaurant.
- Sibling Yin-Yang: With his brother, Sam.
- Sir Swears-a-Lot.
- All Girls Want Bad Boys: Again subverted in that she thinks Nerds Are Sexy.
- Girlish Pig Tails.
- Nerds Are Virgins: It's implied she's had sex despite being a Dungeons and Dragons player herself.
- Nerds Are Sexy: See All Girls Want Bad Boys.
- Nice Guy: Female version. So much so she lets Elly rest in her lap even though they had never met. This is lampshaded in the guest photo comic..
- Plucky Girl.
- Shrinking Violet.
- Beware the Nice Ones: Sam goes off on Harry the Hipster for interrupting him, making him cry.
- Dogged Nice Guy.
- Sibling Yin-Yang: With his brother, Jason.
- Talking to Themself: Sam speaks to a hallucination of his life before he got promoted at his job.
Nick (Poor) Trotmann:
- Author Avatar: The author wrote in a news post that he writes Poor Trotmann when he's most depressed.
- Butt-Monkey: Specifically THE AUTHOR'S Butt-Monkey.
- Cannot Spit It Out: He often says "uh" and "um" when speaking.
- Cannot Talk to Women.
- Chew Toy: Adopted by Yorick.
- Deus Angst Machina.
- Spell My Name with an "S": Two t's, two n's.
- Stalker with a Crush.
- Talking to Themself: Trotmann refers to himself in the second person in his thought bubbles.
Elienne (Elly) Collins:
- All Girls Want Bad Boys: Subverted as she dates Harry and sleeps with John despite the fact neither of them are bad boys.
- Angrish: During her breakdown.
- Embarrassing First Name: Elienne.
- Fiery Redhead.
- Love Martyr: Elly sticks by Harry despite the fact she's not happy in the relationship.
- Rebellious Spirit.
Harry the Hipster Byrnewald:
- Badass Mustache: Openly subverted.
- Clingy Jealous Girl: Inverted.
- Hipster: It's in his name, for God's sake.
- Secret Police: Harry is tasked by his father, the Mayor, to infiltrate and destroy groups he finds undesirable.
- Sunglasses at Night: Harry wears his aviators IN THE TUB.