Jackson White Unpacks Stephen And Lydia’s Mysterious ‘Tell Me Lies’ Engagement: “He’s So Messed Up”

After the Season 1 finale of Tell Me Lies shocked fans by revealing that Stephen (Jackson White) and Lydia (Natalee Linez) are engaged in 2015, the general reaction from viewers was “HOW?! WHY?! WHEN?!”

Three episodes into Season 2 of Meaghan Oppenheimer’s addicting Hulu drama, we still don’t know how or when Lucy’s (Grace Van Patten) ex-boyfriend and ex-best friend got together — nor do we know why exactly Lucy and Lydia had a falling out or why Stephen and Diana (Alicia Crowder) broke up. But thanks to Tell Me Lies star Jackson White, we do have some insight into why Stephen and Lydia become an item.

When chatting with White ahead of Tell Me Lies‘ Season 2 premiere, Decider asked if he believes that Stephen’s love of revenge fueled his engagement with Lydia, or if his character truly had feelings for Lucy’s ex-bestie.

“Gosh, it’s hard to say. I think he genuinely finds something he loves or admires in the people he’s dating, but there’s like this certain layer — maybe that’s even part of the manipulation, is he’s manipulating himself,” White told Decider. “He’s so deep, man. He’s so messed up. So I feel like, it’s probably both.”

While White obviously couldn’t spoil any future Tell Me Lies twists or storylines, he did say, “I think it’s pretty impressive the lengths [Stephen] will go to to get one over on someone.” After reflecting on the question a bit longer, he shared another potential factor behind Stephen and Lydia’s unexpected relationship.

“I think her family is really well off. And he tends to go for girls with families that are well off,” White explained. “That seems to be a theme there. So probably some of that, too.”

As of Tell Me Lies Season 2, Episode 3, Stephen and Diana (whose family is very well off) are still dating in 2008, but a massive Season 2 premiere twist revealed that when Stephen is engaged to Lydia in 2015, Diana is dating PIPPA (Sonia Mena)!

“I didn’t see it coming, so I was like, ‘Oh my gosh, if I’m surprised, then hopefully other people will be as surprised by it,'” Mena told Decider. “I was definitely shocked. Like, did not see that coming in at all. And it was so much fun,” Crowder added.

While we’ll have to wait for more answers to all of our burning Tell Me Lies relationship questions, showrunner Meaghan Oppenheimer assured us they’re coming.

“All the unanswered questions where people are like, ‘How the heck did that come to be?’ We will dive into all of those things: How did Stephen get together with Lydia? Where did his relationship with Diana go? When was the last time Lucy and Steven actually were together? Because it wasn’t the Hawaiian party. There’s more entanglement. That wasn’t their last breakup, I would say. So yes, I have a lot planned,” Oppenheimer told Decider.

As for what goes down in the time that passes between the 2008 college experience and the 2015 wedding festivities, Oppenheimer says she’s open to exploring those years as well.

“Obviously there’s so much that has to happen in the eight years that we have not seen. So yeah, I think it would be nice to see more of that,” she said.

New episodes of Tell Me Lies Season 2 premiere Wednesdays on Hulu. While you wait to see what’s next, be sure to catch up on all of Decider’s Tell Me Lies coverage and interviews here.