One of the biggest mysteries surrounding The Vampire Diaries Season 5 is Grayson Gilbert and how he was involved with the Augustine Society. We know Elena’s dad hated vampires, but would he really go as far as to torture them?

The Season 5 mid-season finale (“Fifty Shades of Grayson”) will feature flashbacks to Elena’s past, and she’ll start to see Gilbert Grayson in a new light.

“She's kind of putting it together and it will emerge as, ‘Oh, I thought that was one thing and looking through it in a different lens my childhood was actually different than I lived it,’” Vampire Diaries executive producer Caroline Dries told TVGuide.com. “We get to learn more about [Gilbert] Grayson's backstory.”

It’s possible that while on Dr. Wes’ lab table, Elena starts to learn about the Augustine Society’s motivations. Perhaps they’re not the monsters she thought they were. Whereas Damon was emotionally scarred from the experimentation, Elena will have quite a different reaction.

“It actually strangely has the opposite effect on her and as she starts to learn more about why Augustine exists, she has a surprising take-away from it,” the EP teased. “That's going to cause some friction between Damon and her.”

It sounds like Gilbert Grayson had a clear motive for joining Augustine, and perhaps, the Society’s objectives aren’t that monstrous after all.

What do you think, TVD fans? What do you think the Augustine Society wants? Sound off in the comments!

Catch the next episode of The Vampire Diaries on Thursday, December 12 at 8 p.m. ET on the CW, followed by an all-new episode of Reign.

Crystal Bell is an editor at Wetpaint Entertainment and our resident fangirl for all things The Vampire Diaries. Follow her on Twitter and Google+!