- Heartless, Claudia Stein, or Claudie is a mobster and tattoo artist in Smile!
- Heartless appears to be a very stoic and emotionless character. Though she can be seen smiling in a smug sort of manner in her first official release art, most of her pre-release sketches and doodles have showed her to be largely devoid of visible emotion.
- Heartless is a tall, somewhat gargantuan woman. She stands at an unusual height and is at an excessively large weight. Though she remains fit enough to remain on her feet despite her size. Given she is a member of the Syndicate and as such, a mobster, it is likely she is very muscular in addition. Her hairstyle is a hot pink leopard print death hawk with straight cut bangs. The 'leopard spots' and the tips and tails of her haircut are black. She is covered in tattoos, including a heart shaped tattoo over her left breast which appears to be a reference to her Syndicate name. Another visible tattoo is an anarchy symbol on her left thigh under the stylized word "Love" which can be read backward as "Hate." She also has some larger tattoo surrounded in doves on her left bicep. Heartless wears heavy gothic inspired makeup that ends in a little spiral under her left eye and has a bracelet tattoo on her right wrist. Both her ears are pierced with oversized spiral horn ear gauges. Her eyes are hazel brown.
- Pesky is her partner in crime, and a fellow Syndicate member.
- Heartless was originally a character in Pineapple Soda but became a character in the spin-off series Smile! abruptly and with little explanation. Due to the disparities in time-period between the two series, (EG: Pineapple Soda taking place mainly in 1996 and Smile! in present day,) it is unclear if she will still make an appearance in Pineapple Soda. It is still feasible given that time travel is a recurring theme within both series.
- Some pre-release drawings of Heartless shows her with dreadlocks and green hair. Other differences include the position of her tattoo, her earrings being biohazard symbols, and differences in her makeup design. It isn't yet clear if changes to her hairstyle and makeup will be a common theme in the series or if the design changes are permanent.
- Heartless can be reached through the ask-the-characters official discord by mentioning her name or by sending a question addressed to a cupid's arrow through heart emoji.