An energetic 25-year old, he is the lead singer and guitarist of the band Checkerboard, which he had formed with his friends back in high school. Starts a relationship with Mark at the beginning of the comic, and it's revealed that he's actually liked Mark for years now, forming a crush on him when they first met. He won't admit this to Mark, though. His best friend is Sarah.
- Attention Whore: Acts like one frequently, which is discussed in the comic. He's trying to be better about it now, though.
- Big Brother Instinct: Towards Sarah, although they're not related.
- Hair-Trigger Temper: Played for Laughs though.
- Keet: He's very energetic and upbeat.
- Mistaken for Cheating: When he starts hanging out with Dannyboy.
- Mr. Fanservice
- Shirtless Scene: Has lots of them.
The drummer of Checkerboard, he is usually a pretty chill guy, but he can be uptight and stubborn at times. Forms a relationship with Toby at the beginning of the comic, although it's not been revealed what Mark likes Toby for (not that Toby doesn't have good qualities, it's just that Mark refuses to tell Toby why he likes him). Was at odds with Kate for a while, but they have since become friends.
- Crazy Jealous Guy: When Toby gives Dannyboy his number, he becomes this.
- Cuteness Proximity: When Dannyboy's cat jumps onto his lap.
- The Dandy: His character profile says he likes to keep up with the latest fashion trends, which really shows in the comic.
- Mr. Fanservice
- Kindhearted Cat Lover: He really likes cats.
- Sharp-Dressed Man: He makes sure he's this.
- Shirtless Scene: A lot.
She is Toby's best friend, acting as a more grounded, yet equally nerdy counterpart. She loves video games and watching porn with Toby for fun. Kate doesn't like her due to her closeness with Toby. Becomes friends with Nathan after they bond over their love of video games.
- Fag Hag: Her two good friends are both gay and in a relationship with each other.
- Gamer Chick: She loves to play video games.
- In-Joke: Has a ton with Toby, to the point where they end up unintentionally shutting other people out.
- Like Brother and Sister: Her and Toby.
- Third Wheel: Subverted. She and Toby are so close they actually end up leaving Mark out.
- Unrequited Love: In a bonus comic about their high school years, Sarah forms a crush on an unnamed guy and writes him a letter confessing her feelings. He threw it in the trash without even reading it, and shows up at a party in the present, trying to take advantage of Sarah's former feelings for him.
The bassist for Checkerboard, Katherine is a rather cold woman who is Toby's on-again, off-again girlfriend. It is her breaking it off with him again over text that sparks Toby and Mark's relationship. She doesn't like Sarah due to how close she is with Toby.
- Defrosting Ice Queen: Gradually starts to interact with the other characters more throughout the comic.
- Jerkass: Although it's been stated that she has mental issues, which most likely cause some of it.
- Jerk with a Heart of Gold: The more screen time she gets, the more fleshed out she becomes, and we realize she's not as bad as she seems.
- Mistaken for Romance: She thinks that Toby and Sarah are actually dating.
- The Quiet One: Back when she was in high school, she was this.
- Sugar-and-Ice Personality: She doesn't show her real emotions to people frequently, instead acting cold and harsh.
- Tsundere: A mild version.
- Unrequited Love: She's in love with Toby, despite their frequent breakups, and wishes she could be nicer to him.
The lead singer of the band Midnight Mischief, Dannyboy starts out as a sort of antagonist, being in a rival band, but he starts showing an interest in Toby, to Mark's dismay. After everything becomes cleared up, however, Dannyboy becomes good friends with Checkerboard, even giving Toby relationship advice.
- Camp Gay: He's flamboyantly gay.
- Commonality Connection: Finds one with Toby in their shared love of Neon Genesis Evangelion.
- Fiery Red Head: He's quite boisterous and loud.
- Gay Best Friend: To Nathan.
- Gayngst: Hinted at, as he mentiopns his parents didn't want him anymore and that he was bullied all the time.
- Keet: Like Toby, he's very energetic.
- Kindhearted Cat Lover: Nathan says he wants to become an old cat lady.
- Lonely Together: He and Nathan when they were in school.
- The Twink: Has some characteristics of one.
- You're Not My Type: Says this to Toby in order to make it clear he's not actually interested.
The drummer of Midnight Mischief, he is best friends with Dannyboy, having known him since middle school. Despite his scary looks, he is actually quite nice and laid back. He forms a connection with Sarah over video games.
- Fag Stag: He's the only straight guy in Midnight Mischief.
- A Friend in Need: He stands up for Dannyboy and is persecuted along with him.
- formerly fat: he used to be fat in high school, but then took up wrestling.
- Gentle Giant: He looks intimidating, but he's actually quite sweet.
- Lonely Together: He and Dannyboy in school, as they were both bullied by everyone else.
- Nice Guy
- Only Friend: Was this to Dannyboy back in school.
The bassist of Midnight Mischief, David is quieter than both Danny and Nathan. He's also thirty years old, making him around five years older than the main cast. His uncle is good friends with Nathan's father.
- Cool Old Guy: He's only thirty years old, but he already acts like this.
- The Quiet One: He's quieter than Nathan and Danny, but he'll open up easily.
- Smoking Is Cool: He's almost always seen with a cigarette.
- Straight Gay: He doesn't have many effeminate qualities, and the readers would have never guessed he liked men if it wasn't explicitly stated.
