This Time Around 2003

In eighth grade, Melissa Rochester is a shy, geeky girl who harbors a massive crush on Drew Hesler, the most popular boy in her middle school. When her missing notebook—stuffed with doodles of their names—finds its way to the school reception desk, it circulates until it lands in the hands of Drew Hesler and his in‑crowd. They decide to pull a prank: a note supposedly from Drew telling Melissa to meet him at lunch and wait to be asked out. Ecstatic at the prospect, and bolstered by her best friend Gabby Castellani, Melissa approaches Drew during lunch. But the moment she gets close, the group publicly reveals it as a joke, leaving Melissa humiliated and racing away. We later learn that both Melissa and Gabby Castellani transfer to a Catholic high school, leaving the public school behind.

Ten years pass, and Melissa has grown into a confident executive at a public relations firm, yet trust issues cling to her after the old humiliation. Her agency is tasked with handling the launch of Drew Hesler’s new restaurant, and at first she resists. Gabby encourages her to see this as an opportunity to exact a quiet revenge: make Drew Hesler fall in love with her and then break his heart.

The plan unfolds in stages. The two women employ a mix of charm, timing, and persistence to draw Drew back into Melissa’s orbit, and he eventually asks her out. They share a tender, intimate date at the still-new restaurant, where Drew explains that the venture is funded from his own money and that if it fails, he would be ruined financially. He also reveals that he has just ended a long relationship with Cara Cabot, the popular girl from their old school who had been by his side for a decade, and he’s ready to move forward. As the night progresses, a genuine spark seems to flare between Melissa and Drew.

Yet the back‑story haunts them. Cara Cabot appears, urging Melissa to step aside, and Melissa’s recent misgivings surface when Cara’s mother—having learned rumors about Melissa’s junior high identity as “Pissy Missy”—tells Cara that Melissa might be more trouble than she’s worth. Drew feels a twinge of guilt for the pranks of their past and heads to Melissa’s apartment, while Gabby realizes their sabotage may have gone too far. She and Cara conspire to push Drew away, but Drew insists that he isn’t the same kid he was back then and that he has moved on.

When Cara and her allies reveal the ruse to Drew, he confronts the truth: his actions in junior high were childish, and he’s not willing to repeat the same mistakes. Gabby recognizes her miscalculation and capitulates, inviting Melissa to join them for Drew’s grand opening that night. At the event, Melissa arrives, they clear the air, and Drew publicly acknowledges Melissa’s hard work. The evening ends with a heartfelt reconciliation and a kiss, signaling a fresh start built on mutual respect and a renewed sense of possibility. The story closes on a note of tempered redemption, showing two people who have learned to separate past wounds from present feelings and to choose a future together.