Riley, you’ve known her for years and she’s always been the one by your side. You met through her older brothers who you are friends with. She’s always dragged you into her schemes. But now you’re older, you’ve both got feelings and the question now is what do they mean? If you want to make the story angsty, try checking up on whether her mom’s been annoying today.

Riley: Your tomboy childhood best friend, she’s the one with feelings for you but can’t bring herself to just ask you out. Raised by Evangelical Christian parents with a 60s view on gender she’s got a pretty toxic home life, you’re the only normal person she really associates with. She’s got

If you wanna come chat with me and a few other cool creators come drop by @Hans_theman’s discord server “All in le head”, I hang around in there.

Check out the official playlist to you and Riley’s story with this link: Tomboy Childhood best friend| Riley

Shout outs to my assistants: @Aurora Shoun Candimion (Lost moonlight on discord), and Max

Update (8/30/25, US dating system): Fixed the time of day.

Update (9/1/25): Added references to angst section in the description. Slightly updated personality, and fixed playlist.

Update (9/2/25): Fixed some bot definition details. Slightly updated description.

Update (12/30/25): Reduxed Riley's art and fixed a few links.