When John Gilbert is twenty two, he returns home for the annual Founder's Day party and when he gets to his brother's house, Grayson introduces him to the very adorable Elena and Jeremy Gilbert. Later, at the party, he is introduced to Miranda's enchanting but still seventeen year old younger sister, Jenna, who is watching the kids as their parents mingle.
John has to remind himself to breathe when Miranda makes the introductions. He is not so sure if it is from being reintroduced to his daughter and her cousin as their uncle or at meeting the beautiful girl acting as caretaker.
Grayson ignores his brother's sadness and focus on the expression of lust on John's face and later pulls him aside to lecture him on the importance of being friendly to the girl—but not overly friendly—and to not say anything about the nature of Elena's parentage.
John rolls his eyes. "I don't even know them, Gray," he protests. "Nothing is going to happen."
"Just be careful," Grayson warns.
John wants to ask more, but he doesn't.
In the end, John sits next to her at dinner and makes conversation with Jenna about Elena and baby Jeremy and engages his daughter/niece as stiffly as he can manage without tipping Jenna off and politely asks her to dance when Grayson and Miranda come to spend time with their children. Jenna's smile is brilliant and John promises himself that he will not mess it up with her and Elena. He likes Jenna and he likes that being near her allows him some resemblance of access to his daughter.
A few weeks and half a bottle of tequila later, Jenna tells him that her asshole of a boyfriend cheated on her.
"What did you expect?" John replies after her confession. "The dumbass is a Fell."
Jenna laughs and kisses him.
Tequila kisses and drunken touches aside, nothing happens until after her eighteenth birthday and, even after that, he has to wait until her latest breakup with Logan Fell.
They are by no means exclusive, but for some reason, it hurts every time he comes into town and sees her out with Logan or talking to Mason Lockwood or one of the Bradley boys. He can't tell her this, though, because it was his idea all along to be able to date other people.
He also can't explain to her the reason he has becomes so distant with his family. How can he explain—without actually saying the words—that watching his daughter call his brother 'Daddy' just about breaks his heart and that there is nothing she can do about it.
He thought being with Jenna would be good for him, that seeing his daughter would be good for him, but it isn't, and eventually he leaves.
It takes him almost sixteen years to realize that leaving changed nothing. It didn't make him stop missing Jenna, it didn't make him stop wishing they could have had a family one day, and it didn't make him stop wishing for his daughter to call him 'Daddy.' So he goes back.
The whole of Mystic Falls hasn't changed a bit—ridiculous town events and pretentious Founding Families wherever you go—but when he sees Jenna and Elena, he realizes just how much the people he has considered his family for the past seventeen years changed.
His daughter hates him, Jenna hates him, and Jeremy barely knows him.
It nearly breaks what is left of his heart, but he doesn't show it. Instead he remembers his promise, and while he knows he has fucked up royally, he realizes that he must do whatever it takes to protect them. However he can.