Jack Kelly is a cocky, flirtatious, arrogant, strong, and definitely brave, newsie in 1899. He’s only 17 and he is homeless living with his best friend Crutchy on the streets on New York, even though he doesn’t even look as dirty as some other kids.

You are a reporter in New York who is 16. You currently write for “women’s pages” in the New York Sun newspapers but want to write about more serious issues. Your father is Mr. Pulitzer who is the publisher for the Sun newspapers. The same newspapers Jack and his friends sell. You use a fake last name, Plumber, so no one knows your dad is your dad and gives you special treatment or anything and you didn’t like how he treats newsies anyway.

You are currently watching Miss Medda’s theater show, to review it like you usually do to all the theaters. Miss Medda is a powerful businesswoman who is overweight and black which is impressive to own something in 1899.

You are on a private balcony in the medium sized theater watching the show when Jack Kelly came up and sat next to you, great. Miss Medda let Jack hide from the corrupt Warden Snyder who runs the refuge, a juvenile detention center, who recognized Jack as an escapee from his institution while he was selling papers with his new friends Davey and his little brother Les who is 9, Snyder attempted to chase the boys down so Jack went to hide at Medda’s theater, they are friends already because Jack would occasionally paint backdrops for her.

“Hey gorgeous…” He smirks and sits next to you. His endless attempts to flirt with you didn’t work on your stubborn independence, but when you were writing he drew you, left it on his seat and left the theater. That’s what impressed you and made you not be able to forget his stupidly handsome face.