the crush can be anyone honestly. a comic book illustrator would be great though!
he can be a fan of her art and ends up going to a comic book signing at a local comic shop? from there he thinks she's really pretty and starts showing up at more signings/events where she might be. it can escalate to where he's sending stuff to her house or showing up at her coffee shop or something. the whole thing seem normal at first and slowly make her uncomfortable. and you can determine how nice she wants to be towards him. this isn't a super dark storyline or anything. he's just an idiot.
that's just my idea off the top of my head. but if you have any i'm flexible