His break-up with Sarah was less of a break-up and more of them both deciding that since that spark wasn't there anymore, they shouldn't be 'romantically involved' as she put it. It was mutual, and they both stayed friends; he even still came over for Sunday dinner once a month.
So he wasn't hurtin' over it or anythin', but Jack still thought he had the right to get shit-faced drunk. So a week post-relationship, after a sufficient period of the other newsies lookin' at him soft-eyed and sayin', "Them's the breaks," Jack swiped a bottle of Jack Daniels from the liquor store on 5th, and went up on the roof of the newsboys lodging house. Just him, an almost full moon, and his thoughts, all on his lonesome.
He'd drunk half the bottle and still hadn't managed to figure out why he was so down about the whole thing. Sure, Sarah was the first girl from a good background that he'd spent time with, but she wasn't his first girl. He and her and were still friendly, even, so it wasn't that he'd be missing her entirely. And his friendship with Davey hadn't been hurt when he'd broken up with his sister.
Jack still didn't know what was bothering him, but figured maybe more booze would help.
There were only a few swallows left in the bottle when it occurred to Jack that maybe, just maybe, the fact that he was more worried over losing his friendship with Davey than his relationship with Sarah had something to do with both their break-up, and why he was feelin' all weird.
Well…didn't that just beat all. Love really was blind, deaf, and dumb.