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They're teenagers on the verge of the rest of their lives, and Kent can't sleep.
Fandoms: Check Please! (Webcomic)
22 May 2017
“This could’ve easily been you, Zimms. You could’ve been the one to OD before the draft. You could’ve gone to Samwell. You could’ve taken the long way to get to the NHL.”
Or, Kent’s and Jack’s roles are reversed and Jack goes straight to the NHL and Kent somehow ends up at Samwell.
The story begins with a draft.
Even though they're linemates, Jack doesn't know Kent all that well. He certainly doesn't expect the American to come look after him when he's unwell on their first roadie.