Jesse: 1st date
Ryder: when he serenaded you in Glee club
Jake: at prom
Puck: when you told him how upset you were with Jake
Sebastian: 1st Date
Hunter: When he met you
Blaine: 2nd date
Finn: When he dumped Rachel for you
Sam: when he suggested you 'test out his Trouty mouth'
Mike: when he won a dance competition
Artie: when you watched his film about you
Kurt: when you got protective of him
Don't ask about the Sam one, a friend suggested it...
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Glee Preferences and Imagines
FanficI decided to write one of these because very few get continued or have very few chapters.