Top 5 Best & 5 Worst Rom-Com Dates

#5: Best: IKEA Date

“(500) Days of Summer” (2009)

It’s practically a universal truth that IKEA can make or break a relationship, and for Tom and Summer, it becomes one of the most charming dates imaginable. They wander through staged rooms, flop onto beds, and test furniture meant for display only. They make their way through the store, playing house like it’s been 34 years instead of 34 days. Tom plays along, already picturing a life that sadly won’t happen. Shoppers shuffle past while they build an imaginary life full of domestic bliss. It’s light, goofy, and strangely intimate. For a moment, the fluorescent lights disappear, and it feels like they’ve found a tiny world that belongs only to them.

#5: Worst: Where to Begin!?

“How to Lose a Guy in 10 Days” (2003)

The only reason these dates don’t rank higher is that they’re deliberately bad. Andie systematically chips away at Ben’s patience, turning what should be a fun night into a public ordeal. At the NBA game, she goes out of her way to make sure Ben enjoys as little of the action as possible. Then she dangles a ‘do-over,’ which predictably turns into another one of her self-serving antics, far from the night he truly wanted. Then there’s the dinner scene: Andie really will do anything to get her story! Meanwhile, it’s amazing just how much his ego can take, enduring hit after hit, all for the sake of winning a bet.

#4: Best: Griffith Observatory Dance

“La La Land” (2016)

This date is an absolute dream because it transcends reality, offering a truly ethereal experience that is nothing short of breathtaking. Mia and Sebastian start with a simple visit to the planetarium, then suddenly lift off the ground, floating into the stars. They dance through a glowing universe, twirling among constellations and drifting past nebulae as if nothing else exists. Their silhouettes move together in perfect rhythm, suspended in endless space. The scene captures that feeling of new love when everything feels possible, and the world briefly disappears. For a moment, nothing else matters. It’s dreamy, intimate, and completely untethered from reality.

#4: Worst: Double Date

“When Harry Met Sally…” (1989)

Few dating scenarios are as mortifying as this double date gone wrong. It perfectly illustrates the excruciating awkwardness of being the unwelcome third (or fourth) wheel when your friends unexpectedly hit it off. Harry and Sally’s attempt to set each other up with Marie and Jess goes spectacularly awry. We see Harry and Sally’s hopeful expressions slowly deflate into discomfort as Marie and Jess immediately connect, and basically forget they’re even on a double date. Our protagonists are left making strained small talk, clearly playing gooseberry while their friends fall for each other instead. It's a relatable, albeit painful, scenario that highlights how some dates just aren't meant to be.

#3: Best: Paintballing

“10 Things I Hate About You” (1999)

Some people hope to get struck by Cupid’s arrows, while others are happy getting splattered by a paintball. Kat and Patrick charge through the paintball field, dodging shots and firing back without hesitation. Paint splatters everywhere as they run around, laughing and fully locked into the game. They duck behind barriers, strategize on the fly, and eventually collapse together, breathless and grinning. There’s no pressure to impress, no polite conversation. Their connection shows up in the way they challenge each other and keep pace. The messiness is the point. It’s playful, competitive, and honest, proving attraction can spark when people are fully themselves.

#3: Worst: A Night Behind Bars

“Blind Date” (1987)

Walter’s date with Nadia spirals out of control at an alarming pace. What starts as a formal dinner quickly explodes when champagne takes hold of Nadia, costing Walter a major deal and his job. The chaos only escalates. He’s chased through the city by her ex, his car is stripped, and the madness just continues to devolve. By the time he reaches a party, he’s frantic, unraveling, and barely holding himself together. His behavior turns embarrassing, then violent, ending in a brawl. Flashing police lights follow and the night ends in a cold station cell. He’s eventually bailed him out of a situation that completely wrecked his life.

#2: Best: Ice Skating

“Serendipity” (2001)

This charming date is a winter wonderland dream, wrapping you in the warmth of a frozen-in-time fairy tale in the middle of a bustling city. Jonathan and Sara share a whimsical, almost fated ice-skating date at Wollman Rink in Central Park. The crisp winter air brushes past them, and city lights twinkle like scattered diamonds. Their graceful glides across the ice fall into rhythm, playful spins, and intimate glances punctuating each lap. The setting encourages realness and fun, allowing their connection to grow naturally, creating a budding romance that feels lifted straight from a storybook. Well, that is, until Sara brings them crashing to reality.

#2: Worst: A Spicy-Induced Flare-Up

“Along Came Polly” (2004)

This date is a testament to showing up as your authentic self. Reuben's attempt to impress Polly at a Moroccan restaurant turns into a spectacle of gastronomic regret. At first, he insists he can handle the spice, sitting upright and confident. Then the heat kicks in. His face reddens, sweat beads on his forehead, and frantic sips of water offer no relief as the food takes its toll. Each bite makes things worse, and his discomfort becomes impossible to ignore. The situation reaches a breaking point with the explosive aftermath, proving that faking it to impress someone can lead to a messy date. At least their salsa date is más caliente.

Before we unveil our top picks, here are a few honorable mentions.

Best: Spaghetti & Meatballs, “Lady and the Tramp” (1955)

Private Dining, Free Food Under the Stars with Live Music? Sign Us Up!

Worst: TMI, “Baby Mama” (2008)

Nothing Screams “Run for the Hills” Like Leading with Your Biological Clock on a First Blind Date

Best: Razzles & a Swing Set, “13 Going on 30” (2004)

Relive Your Childhood Joy & Find Romance on the Swings with Razzles in Hand

Worst: Robot Concert, “The Perfect Man” (2005)

Sure, If It’s Your Thing Why Not, but Based on Jean’s Face This Is Not the One

#1: Best: The Spanish Steps Rendezvous

“Roman Holiday” (1953)

What is it about Europe that just screams romance? This Roman escapade is pure dating fantasy, blending freedom, spontaneity, and the thrill of discovering true connection in one of the world’s most iconic cities. Princess Ann, played by Audrey Hepburn, experiences exhilaration as she escapes her royal duties with American journalist Joe Bradley. We watch her joyously eating gelato on the Spanish Steps, and follow them as they zip through Rome on a Vespa, carefree and unburdened. Every moment feels impromptu, shedding inhibitions and inviting romance, capturing the magic of a blossoming connection against breathtaking historic beauty. To borrow from another Rome-based flick, this is what dreams are made of.

#1: Worst: Caught in a Zip

“There's Something About Mary” (1998)

This date is infamous for all the wrong reasons, starting with a zipper disaster that ruins the night before it even begins. Ted’s attempt to take Mary to prom ends in frantic scrambling, a trip to the emergency room, and the complete collapse of his first impression. The zipper incident dominates every moment, leaving Ted embarrassed, flustered, and painfully aware of everyone watching. Then, years later, Mary unknowingly applies a mysterious bodily substance to her hair, mistaking it for gel, and Ted can only watch in horrified disbelief. This gross misunderstanding is the absolute epitome of cringeworthy, a literal sticky situation no one wants to find themselves in, like ever.

What would be your dream date inspired by a rom-com, and which would have you faking an emergency just to get away? Let us know in the comments