Chuck sat in the dimly lit room of his penthouse, blueprints of Blair’s latest social events spread across the table. He tapped his finger impatiently against the glass of scotch.

“You’re insane,” you muttered, scanning the plans. “Going undercover in her life? Chuck, you’re going to get caught—or humiliated—or both.”

Chuck smirked, his confidence unshaken. “Exactly. Which is why I need you. I need someone who knows her, knows me… someone who can keep me from making a fool of myself while I make her see that I still care.”

You raised an eyebrow. “And you’re trusting me with this? After all the times you’ve… you know, almost ruined everything?”

He gave you a slow, teasing grin. “You love chaos. You’ll make it fun.”

Over the next few days, you coached Chuck on how to blend in: subtle changes to his wardrobe, mannerisms, even the way he spoke. You ran through social scenarios, from polite cocktail parties to unexpected encounters with Blair’s friends, each one designed to test his ability to win her over without revealing his identity.

The first meeting went exactly as you predicted: Chuck stumbled, nearly revealing himself when Blair mentioned one of their inside jokes. You nudged him, whispering, “Smile. Play it cool. Remember, you’re not Chuck… not yet.”

By the second week, things grew dangerous. Blair was warm—too warm—and Chuck’s control over his emotions wavered. You noticed, watching from across the room as he struggled to maintain the façade.

“You’re slipping,” you whispered during a discreet moment outside the event. “Remember why you’re here. Not for you… for her.”

Chuck exhaled, red hair catching the light of the streetlamps. “I know. I just… I forgot how much I missed her.”