Trevor Belmont, the 9th Doctor, Detective Pikachu, Edward Elric, Detective Jake Peralta with prompt 10
"To cut and style my hair." Oho this'll be interesting.
Nine (yeah he's short-haired but I bet he's earned a lot about it along the way)
Jake Peralta (from the many clips and memes I've seen of B99, he gives off enough Big City Disaster Bi Energy that I'd feel reasonably comfortably leaving this to him)
Trevor Belmont (another Disaster Bi, but I suspect about 80% of his experience is from occasionally chopping his own hair with whatever sharp object he happened to have to hand. Granted, the other 20% is from the popular fanon that he had several older sisters, and you can't tell me they didn't show him some hair stuff)
Edward Elric (okay kid your hair is amazing but I stg if you get any of mine gets caught in your automail then I will rip it from its socket)
Detective Pikachu (he hands too small)