It Had to Be You 2000

At The Plaza in Manhattan, Charlie Hudson and Anna Penn find themselves thrust into wedding planning when their respective fiancés, Claire Parker and David Allen, are abroad in Europe for work. The pair’s paths cross in a serendipitous ripple of encounters: first at a reception, then again in an elevator, and once more as they separately enter a wedding-shopping world that hums with questions about commitment and chance.

Charlie Hudson invites his close friend Henry Taylor to dinner, and amid the flame of attraction, Anna’s presence lights up the room. The spark is undeniable, and the two share a moment that hints at something deeper than casual flirtation. Their elevator rendezvous repeats the tension, and Anna jests with a guarded warmth as she tries to navigate the growing pull between them.

That night, a small, almost cinematic mishap—Anna falling asleep in the tub with water spilling onto Charlie’s bed—forces a brief interruption in the mood, and Charlie heads upstairs to address the maintenance issue. The incident becomes a quiet reminder of how ordinary moments can tilt a life toward something new, something unexpected.

The next day, the two cross paths again in a wedding shop, registering side by side and catching glimpses of each other through the act of choosing rings and gifts. While they split to collect bridal party items, both notice the sales staff weighing in with their blunt, even cynical, views on marriage—an atmosphere that unsettles Anna and nudges Charlie toward honesty about his own feelings.

A dinner invites more intimate conversation. Anna reveals her teaching career, and Charlie opens up about leaving the police force after a devastating failure to prevent a child’s suicide. In parallel, Henry Taylor connects with Anna’s maid of honor, Tracey Meltempi, in a bar, where his charm is tempered by a sincere, non-pressuring approach that steadies Tracey’s expectations.

The couple’s search for a wedding band becomes a reminder of past lives. They encounter an old contact of Charlie’s who’s unsteady after a divorce, and they drop by to see the officiating priest. The encounter unsettles Anna, who retreats to lunch with her mother. The luncheon scene underscores tensions about compatibility and the fear that love might demand more than one is prepared to give.

Anna’s mother voices concerns about settling, and the dynamics with David’s mother—who warns that Charlie’s world could be affected by his past—add layers of familial anxiety to the romantic questions at hand. Charlie and Henry discuss the idea of love at first sight, and Tracey weighs in, encouraging Anna to consider what she really wants.

A pivotal moment comes when Henry nudges Charlie to confess. He rents a horse-drawn carriage, pours champagne, and plans a dramatic reveal. They come close to a kiss, but the reality of Claire and David—and the weight of commitments already chosen—pulls them apart, returning Charlie to his hotel room where Claire awaits.

The emotional arc shifts as the two couples confront the ache of possibilities not yet realized. Claire departs, and a cautious resolve settles over Charlie: he must tell Anna how he feels, even if the timing feels perilous. Anna’s response—fear that her feelings aren’t mutual—forces a pause that feels almost inevitable given the circumstances.

Time passes, and we glimpse the four lead characters resuming their lives: Charlie continues his writing, Anna remains dedicated to her students, Henry confronts his own sobriety, and Tracey seeks out Henry at the bar where their paths first crossed. Yet the pull between Charlie and Anna remains a quiet undertone beneath the surface of everyday life.

A year passes, and Charlie’s new book hits the shelves. An observant colleague hints that the narrative might be about their shared story, sparking Anna’s decision to seek out Tracey. They head to the precinct to find Henry, discovering that he has returned to his police roots and is currently helping a young person wrestling with despair. The reunion is warm yet restrained until a realization crystallizes: Henry is sober, and the trio begins to bridge the gap that once seemed insurmountable. The moment culminates in a hopeful kiss, signaling a renewed possibility for what they might become together.

The story culminates in a wedding scene that finally unites the two central arcs: Charlie and Anna’s wedding, where the journey through doubt, proximity, and courage finds its resolution in a commitment that feels earned and true.

This tale blends quiet humor, risk, and the messy beauty of imperfect timing, offering a portrait of love that can endure the jagged edges of doubt and the weight of life’s complicated obligations, all set against the glamorous backdrop of a quintessential New York landmark.