Dan Humphrey wasn’t the kind of guy anyone expected to be obsessed. He prided himself on being reserved, observant, a little removed from the chaos of Upper East Side drama—even if that was a lie he told himself more often than he should have. But when it came to you, the famous new transfer student with a name that lit up headlines and a face that had become the centerpiece of countless Tumblr blogs and gossip articles, Dan had lost all sense of distance.

He knew everything about you. Not in a creepy way—well, not intentionally. But he read every interview, followed every fan account, even scrolled back years into your Instagram archive just to try and understand the essence of you. It wasn’t just your beauty that pulled him in—it was your effortless poise, the way you somehow stayed grounded despite all the noise around your name. Dan liked to believe he saw the real you, the version hidden behind curated images and stylized red carpet moments. He’d fantasized more times than he could count about what it would be like if you two ever crossed paths. He never imagined it would actually happen.

But there you were.

It was the first morning of the fall semester at Constance Billard-St. Jude’s Academy, and the entire student body was already buzzing with whispers. You were the new girl, the starlet, the internet’s sweetheart—and now, inexplicably, you were walking the same courtyard as them. Dan had only seen you through screens, but the real-life version of you somehow made all those photos feel flat and incomplete.

You stood in front of the school, dressed in a way that made the other girls look like they were trying too hard, your attention locked on your phone, thumb scrolling lazily. The crowd around you gave just enough distance that it was clear they were too intimidated to make the first move. Dan’s heart thudded as he realized what this meant: this was his chance. You hadn’t spoken to anyone yet. You were completely unclaimed. And if he moved now, he could be the first person you really connected with here.

For a moment, he hesitated. Should he act cool, pretend he didn’t already know who you were down to your middle name and past film credits? Or should he be honest—well, selectively honest—and just be himself? But then he remembered all the hours he spent thinking about this exact moment, and how he promised himself he wouldn’t let it slip away. He steadied himself, wiped his palms on his jeans, and walked up to you, determined.

“Hey… uh, hi. Sorry to interrupt you—I know phones are sacred before school starts, believe me—but I just wanted to say welcome. I mean, to Constance and St. Jude’s. I guess you’ll get tired of hearing that today, but… I wanted to be the first to say it. I’m Dan. Dan Humphrey. I go here, obviously. Not that I wouldn’t be loitering outside a school for no reason, that would be… weird.”

He lets out a nervous laugh.

“I’ve, uh… heard a lot about you. Not in a creepy way. Okay, that sounded creepy. I just mean… you’ve got a reputation. The good kind. Impressive. You’ve done a lot for someone our age. Honestly, it’s kind of inspiring. I write a little… well, a lot, actually. Fiction, essays, blog stuff—so people like you… I guess I just find you interesting. In the best way.”

He clears his throat.

“Anyway, if you ever want someone to show you around—someone who’s not drowning in trust fund ego or pretending to care just because of your IMDB page—I’d be happy to help. No pressure or anything. You probably already have ten people offering, but just… if you want something a little less curated, I’m your guy. Well, if you want.”

He offers a small, awkward smile.

“So… yeah. Welcome to this wonderfully twisted place we call school.”