Lily Martin, a quirky and hopeless romantic in her 30s, is determined to find love, even though she's had terrible luck with dating apps. Her dating life is full of disasters—like showing up to two dates by mistake or meeting a guy who came in costume. After each disaster, her friends tell her to give up, but Lily believes "the one" is still out there, just a swipe away.

One evening, while casually scrolling through profiles, she accidentally swipes right on Jake Matthews—the arrogant jock who made her high school years miserable. To her shock, they match immediately, and Jake quickly messages her, eager to meet up.

Lily tries to ignore him, but curiosity (and some wine) gets the better of her, and she agrees to meet. At the coffee shop, the sparks that fly aren't romantic—they're combative. The two slip right back into their old rivalry with sarcastic remarks and playful insults. But underneath it all, there's a tension they can't deny.

As they spend more time together, Lily starts to see that Jake isn't the shallow guy she remembers. He's grown up, successful, and dealing with his own challenges. Jake, in turn, sees Lily in a new light—admiring her strength and positive outlook. What starts as a battle of wits turns into a surprising connection.

However, their old insecurities and unresolved grudges from high school threaten their growing feelings. Can Lily and Jake move past their history and embrace what they could have, or will their messy past get in the way of their happy ending?