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From dreamy fantasy dates to absolute romantic disasters... Join us as we count down our picks for the best and worst dates in romantic comedies! Our countdown includes the IKEA stroll in "(500) Days of Summer," the Observatory dance from "La La Land," the infamous zipper incident from "There's Something About Mary," and more!
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00:00Does he take you out dancing just so he can hold you close?
00:05I don't dance.
00:06Welcome to Ms. Mojo.
00:08And today we're counting down our picks for the rom-com dates that made our dream vision boards.
00:13And the ones that are more like a walking nightmare.
00:17So what's your excuse?
00:18For?
00:19For acting the way we did.
00:22I don't like to do what people expect.
00:26Number 5. Best. Ikea date.
00:29500 days of summer.
00:30It's practically a universal truth that Ikea can make or break a relationship.
00:36And for Tom and Summer, it becomes one of the most charming dates imaginable.
00:40Home sweet home.
00:44Our place really is lovely, isn't it?
00:48Yes.
00:50Ooh, idols on.
00:52They wander through staged rooms, flop onto beds, and test furniture meant for display only.
00:58They make their way through the store, playing house like it's been 34 years instead of 34 days.
01:04I made it myself.
01:06Bald eagle.
01:08Your favorite.
01:16The sink's broken.
01:18Tom plays along, already picturing a life that sadly won't happen.
01:23Shoppers shuffle past while they build an imaginary life full of domestic bliss.
01:27It's light, goofy, and strangely intimate.
01:30For a moment, the fluorescent lights disappear.
01:33And it feels like they've found a tiny world that belongs only to them.
01:38Darling, I don't know how to tell you this, but there's a Chinese family in our bathroom.
01:46Number 5. Worst. Where to begin.
01:49How to lose a guy in 10 days.
01:51The only reason these dates don't rank higher is that they're deliberately bad.
01:55I'm gonna make you wish you were dead.
01:59Poor guy.
02:01Andy systematically chips away at Ben's patience, turning what should be a fun night into a public ordeal.
02:07At the NBA game, she goes out of her way to make sure Ben enjoys as little of the action
02:12as possible.
02:13Watch the three-step trip!
02:13Ben, it's not diet! Ben, it's not diet!
02:17Please, I'm so thirsty!
02:20With the wine! With the wine!
02:22Then she dangles a do-over, which predictably turns into another one of her self-serving antics,
02:28far from the night he truly wanted.
02:30Then there's the dinner scene.
02:32Andy really will do anything to get her story.
02:35Meanwhile, it's amazing just seeing how much his ego can take,
02:39enduring hit after hit, all for the sake of winning a bed.
02:42My boyfriend thinks I'm fat!
02:47And I can't eat in front of you!
02:49I can't eat in front of you!
02:52I can't eat in front of you!
02:54I can't eat in front of you!
02:54Number 4. Best Griffith Observatory Dance, La La Land
02:58This date is an absolute dream because it transcends reality,
03:03offering a truly ethereal experience that is nothing short of breathtaking.
03:17Mia and Sebastian start with a simple visit to the planetarium,
03:21then suddenly lift off the ground, floating into the stars.
03:24They dance through a glowing universe, twirling among constellations and drifting past nebulae
03:30as if nothing else exists.
03:50Their silhouettes move together in perfect rhythm, suspended in endless space.
03:55The scene captures that feeling of new love when everything feels possible,
04:00and the world briefly disappears.
04:02For a moment, nothing else matters.
04:04It's dreamy, intimate, and completely untethered from reality.
04:09Number 4. Worst. Double Date.
04:11When Harry Met Sally
04:12Few dating scenarios are as mortifying as this double date gone wrong.
04:17I thought it was like late 80s.
04:19It's a macho.
04:20I don't think it's just me.
04:21It's interesting.
04:22Let's just say I'm really just not a big fan of Jimmy President.
04:25Well, he's the reason I became a writer, but that's not important.
04:28It perfectly illustrates the excruciating awkwardness
04:32of being the unwelcome third or fourth wheel
04:35when your friends unexpectedly hit it off.
04:37Harry and Sally's attempt to set each other up with Marie and Jess
04:41goes spectacularly awry.
04:43Restaurants are to people in the 80s.
04:45What theater was to people in the 60s?
04:47I read that in a magazine.
04:50I wrote that.
04:52Get out of here.
04:53No, I did. I wrote that.
04:55I've never quoted anything from a magazine in my life.
04:58We see Harry and Sally's hopeful expression slowly deflate into discomfort
05:02as Marie and Jess immediately connect
05:05and basically forget they're even on a double date.
05:07Our protagonists are left making strained small talk,
05:11clearly playing gooseberry while their friends fall for each other instead.
05:14It's a relatable, albeit painful scenario
05:17that highlights how some dates just aren't meant to be.
05:20Don't make any moves tonight.
05:22Fine, no problem. I wasn't even thinking about tonight.
05:26Well, I don't really feel much like walking anymore.
05:28I think I'll get a cab.
05:29I'll go with you.
05:30Great!
05:31Number three. Best. Paintballing.
05:34Ten things I hate about you.
05:36Some people hope to get struck by Cupid's arrows,
05:39while others are happy getting splattered by a paintball.
05:41Are you up for it?
05:44Up for what?
05:51Cat and Patrick charge through the paintball field,
05:55dodging shots and firing back without hesitation.
05:58Paint splatters everywhere as they run around laughing
06:00and fully locked into the game.
06:03They duck behind barriers, strategize on the fly,
06:06and eventually collapse together, breathless and grinning.
06:14There's no pressure to impress, no polite conversation.
06:18Their connection shows up in the way they challenge each other and keep pace.
06:22The messiness is the point.
06:23It's playful, competitive, and honest.
06:26Proving attraction can spark when people are fully themselves.
06:29I'm surprised that you've never been told before
06:34That you're lovely and you're perfect
06:37And that somebody wants you
06:39Number three. Worst. A night behind bars. Blind date.
06:44Walter's date with Nadia spirals out of control at an alarming pace.
06:48What starts as a formal dinner quickly explodes when champagne takes hold of Nadia,
06:53costing Walter a major deal and his job.
06:55Do I have to say the words?
06:58I'm fired.
07:00Fired?
07:00The chaos only escalates.
07:02He's chased through the city by her ex,
07:05his car is stripped,
07:06and the madness just continues to devolve.
07:09By the time he reaches a party,
07:10he's frantic, unraveling, and barely holding himself together.
07:14Lord of us, Mamo King!
07:17No!
07:18No!
07:19Mamo, is it, darling?
07:21Mamo!
07:22Where's my head?
07:23Mamo!
07:24His behavior turns embarrassing, then violent, ending in a brawl.
07:29Flashing police lights follow.
07:31The night ends in a cold station cell,
07:34with Nadia bailing him out of a situation that completely wrecked his life.
07:38I warned you not to let her drink.
07:41Number two. Best. Ice skating. Serendipity.
07:45This charming date is a winter wonderland dream,
07:48wrapping you in the warmth of a frozen-in-time fairy tale
07:51in the middle of a bustling city.
07:53Now promise me you're not just visiting here for a week,
07:55or marrying somebody to get a green card,
07:57or on parole.
08:00None of the above.
08:02You?
08:02No, no, no.
08:03Jonathan and Sarah share a whimsical,
08:06almost faded ice skating date
08:08at Woolman Rink in Central Park.
08:10The crisp winter air brushes past them,
08:12and city lights twinkle like scattered diamonds.
08:15Their graceful glides across the ice fall into rhythm,
08:19playful spins, and intimate glances punctuating each lap.
08:22Favorite New York moment.
08:27This one's climbing the charts.
08:30I'm flattered.
08:32The setting encourages realness and fun,
08:35allowing their connection to grow naturally,
08:37creating a budding romance that feels lifted straight from a storybook.
08:41Well, that is until Sarah brings them crashing to reality.
08:44Let's take a look at that.
08:46Oh, Jesus.
08:48That's a deep, deep gash.
08:51What?
08:52Number two.
08:54Worst.
08:54A spicy-induced flare-up.
08:56Along came Polly.
08:58This date is a testament to showing up as your authentic self.
09:01Ruben's attempt to impress Polly at a Moroccan restaurant
09:04turns into a spectacle of gastronomic regret.
09:08Are you okay?
09:09Because you're sweating pretty profusely.
09:12Yeah, no, I'm fine.
09:13I always react this way to spicy food.
09:15At first, he insists that he can handle the spice,
09:18sitting upright and confident.
09:20Then the heat kicks in.
09:21His face reddens,
09:23sweat beads on his forehead,
09:24and frantic sips of water offer no relief as the food takes its toll.
09:29Are you sure I can't get you a towel or something?
09:31No, no, I'm good.
09:33Each bite makes things worse,
09:34and his discomfort becomes impossible to ignore.
09:37The situation reaches a breaking point with the explosive aftermath,
09:41proving that faking it to impress someone can lead to a messy date.
09:44At least their salsa date is mas caliente.
09:58Before we unveil our top pick,
10:00here are a few honorable mentions.
10:03Best, Spaghetti and Meatballs,
10:04Lady and the Tramp,
10:06Private Dining,
10:07Free Food Under the Stars with Live Music,
10:09sign us up.
10:23Worst, TMI, Baby Mama.
10:25Nothing screams run for the hills
10:27like leading with your biological clock on a first blind date.
10:30I want a baby now.
10:31I'm 37.
10:37It's too much for a first date, isn't it?
10:40I said too much.
10:42I'm just gonna go use them.
10:44Best, Razzles and a Swing Set,
10:4613 going on 30.
10:48Relive your childhood joy
10:50and find romance on the swings with Razzles in hand.
10:53Whoever goes the furthest,
10:54the other owes a drink.
10:55An Orange Julius.
10:56Who up in the steaks?
10:58And dinner Friday night at 8 o'clock
11:01at the 24th Street Diner
11:03to celebrate our redesign being chosen.
11:06Worst, Robot Concert,
11:08The Perfect Man.
11:09Sure, if this is your thing, why not?
11:11But based on Gene's face,
11:13this is not the one.
11:15I don't think that sticks!
11:17Oh, they're Kelroy.
11:18They're a tribute band of sticks.
11:22Yeah, the singer's not as good as the original,
11:24but if you close your eyes,
11:25you can't even tell the difference.
11:28I've got the secret.
11:29No? You can tell.
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11:51What is it about Europe that just screams romance?
11:55This Roman escapade is pure dating fantasy,
11:57blending freedom, spontaneity,
11:59and the thrill of discovering true connection
12:01in one of the world's most iconic cities.
12:03Why don't you take a little time for yourself?
12:07Maybe another hour.
12:09Live dangerously.
12:10Take the whole day.
12:12I could do some of the things I've always wanted to.
12:15Princess Anne, played by Audrey Hepburn,
12:18experiences exhilaration as she escapes her royal duties
12:21with American journalist Joe Bradley.
12:23We watch her joyously eat gelato on the Spanish steps
12:26and follow them as they zip through Rome on a Vespa,
12:30carefree and unburdened.
12:44Every moment feels impromptu,
12:46shedding inhibitions and inviting romance,
12:49capturing the magic of a blossoming connection
12:51against breathtaking historic beauty.
12:53To borrow from another Rome-based flick,
12:56this is what dreams are made of.
12:57Since then, it's become a sort of a shrine.
12:59People come and whenever their wishes are granted,
13:03they put up another one of these little plaques.
13:06Lovely story.
13:08Number one.
13:09Worst.
13:10Caught in a zip.
13:11There's something about Mary.
13:12This date is infamous for all the wrong reasons,
13:15starting with a zipper disaster
13:16that ruins the night before it even begins.
13:19Ted?
13:20Are you okay?
13:22Yeah, I'm fine.
13:23Everything's okay.
13:24Okay, okay, just take your time.
13:26It's all right.
13:27You know, he's been in there over a half an hour.
13:29Ted's attempt to take Mary to prom
13:31ends in frantic scrambling,
13:33a trip to the emergency room,
13:34and the complete collapse of his first impression.
13:37The zipper incident dominates every moment,
13:40leaving Ted embarrassed, flustered,
13:41and painfully aware of everyone watching.
13:44Okay, Ted!
13:45Okay, let's roll.
13:53Then, years later,
13:55Mary unknowingly applies
13:56a mysterious bodily substance to her hair,
13:59mistaking it for gel,
14:00and Ted can only watch in horrified disbelief.
14:03This gross misunderstanding
14:05is the absolute epitome of cringeworthy,
14:07a literal sticky situation
14:09no one wants to find themselves in,
14:11like, ever.
14:12No, no, no, no, God,
14:14I couldn't live with myself.
14:15No, I mean, I only went out with him a couple times,
14:18but, you know, it's like,
14:19just the thought of that.
14:20What would be your dream date
14:22inspired by a rom-com,
14:23and which would have you faking an emergency
14:26just to get away?
14:27Let us know in the comments.
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