The night John Gilbert leaves Mystic Falls, Jenna is little more than sixteen, and she had just told him not but a week ago that she thought she might be in love with him.
"John Gilbert is a complete jackass," Mason says, coming to her spot behind the school bleachers.
He sits down beside her and hands her a flask. "It'll help," he tells her.
She has never had a drink of alcohol before that day, and she doesn't really believe him, but she takes the flask anyway and takes a hesitant swig.
She ends up coughing and spitting it all back up and Mason sits there laughing at her.
"It isn't funny!" Jenna exclaims, crossing her arms over her chest defensively.
Mason takes the flask back and takes a swig expertly. "No, I suppose it isn't."
For the next hour and a half after the football game Jenna will always remember as the one that made her cry and the one that opened the gateway to all her risky behaviors, Mason instructs Jenna on the fine points of liquor and weed and while Jenna tries none of it again that night, she makes him promise to really show her some other time.
"There's a whole world of things I can teach you, Jenna Sommers," Mason whispers against her lips as he drops her off at her house.
And neither is truly surprised when she takes him up on his offer.