Pop culture is suffused with examples of grand romantic gestures. From Tramp offering Lady the last meatball to Arwen the elf choosing to become mortal so she can be with her beau, there’s no shortage of ways that people in television, movies, music, and theater can show their devotion. Which is why it’s a little unsettling to realize just how many of these seemingly beautiful expressions of love are downright disturbing when you take a step back and consider them with an objective eye. What can seem sweet or moving to someone caught up in a story too often would be a cause for police involvement in real life. Please use the following list as a handy example of what not to do the next time you find yourself wanting to make a romantic gesture—at least, if you want to stay on the right side of a restraining order. And because it had far too many examples to overlook, we’ve created a special “Creepy MVP” award at the end of this list for everybody’s favorite British schmaltz-fest: Love, Actually. Advertisement

2 / 30 1. Take over your preteen’s school speech to explain how much you love your ex: Cal Weaver (Steve Carell), Crazy, Stupid, Love List slides 1. Take over your preteen’s school speech to explain how much you love your ex: Cal Weaver (Steve Carell), Crazy, Stupid, Love 1. Take over your preteen’s school speech to explain how much you love your ex: Cal Weaver (Steve Carell), Crazy, Stupid, Love To be fair, the movie does promise Crazy, Stupid, Love, and boy, does it deliver. Underage babysitters, lonely teachers, smooth talkers, and Kevin Bacon flit around each other in varying states of frenzy and obsession, taking everything just too far for comfort. The crowning moment, however, comes when Steve Carell’s Cal helps his son out of his depressing school speech by taking it over completely. Sure, he could have just guided his son offstage and had a private talk with him about his feelings, but why do that when he could usurp the stage to talk about how much he misses his estranged wife (Julianne Moore)? It’s exactly the kind of grand speech that always goes over well in romantic comedies, when in real life, security would—and should—have taken him offstage the second he started. [Caroline Framke]


3 / 30 2. Use your superpowers to stalk your girlfriend: Peter Parker (Andrew Garfield), The Amazing Spider-Man 2 List slides 2. Use your superpowers to stalk your girlfriend: Peter Parker (Andrew Garfield), The Amazing Spider-Man 2 2. Use your superpowers to stalk your girlfriend: Peter Parker (Andrew Garfield), The Amazing Spider-Man 2 Much of The Amazing Spider-Man 2 finds Peter Parker doing battle with that most formidable of foes: his girlfriend’s desire to live her own life. After breaking up with Emma Stone’s Gwen Stacy, Peter adds her photos to his crazy conspiracy wall (with the unnerving note, “Do I have to lose you too??”), then uses his Spidey powers to stalk his ex-girlfriend all around Manhattan. And just as Gwen’s in mortal danger of pursuing her career at Oxford, he scrawls, “I LOVE YOU” on the Brooklyn Bridge, snatches her to the top of it, then insists he’s just “going to follow [her] everywhere,” forever. See, it’s sweet, because she’s literally powerless to resist! [Sean O’Neal] Advertisement

4 / 30 3. Sneak into her bedroom to stare at the human you’re obsessed with while she sleeps: Edward Cullen (Robert Pattinson), Twilight List slides 3. Sneak into her bedroom to stare at the human you’re obsessed with while she sleeps: Edward Cullen (Robert Pattinson), Twilight 3. Sneak into her bedroom to stare at the human you’re obsessed with while she sleeps: Edward Cullen (Robert Pattinson), Twilight With the Twilight series, Stephenie Meyer takes all the clichés of love stories and intensifies them, turning a typical drama of fierce first love into an over-the-top, sometimes abusive relationship, represented in many frightening instances of Edward (Robert Pattinson) exerting control over Bella (Kristen Stewart). Early on in their budding relationship, he climbs through Bella’s bedroom window—without her permission—making her gasp when she sees him. It’s a common enough occurrence in romance stories, meaning Meyer will take it to the next level. Sure enough, when Bella asks Edward if he climbs through windows a lot, he smirks and replies, “Just the past couple months.” Instead of recoiling in terror, Bella appears flattered and like she really wants to kiss him. But Edward’s not done. “I like watching you sleep. It’s kind of fascinating to me.” Real-world consequences would start with that startled gasp and include, at the very least, a conversation about respect, if not an outright break-up then and there. Here, it ends with an intense first kiss that Edward initiates and Bella ends up apologizing for. [Caitlin PenzeyMoog] Advertisement

5 / 30 4. Travel back in time to an era without modern medicine, electronics, or equal rights for women: Kate McKay (Meg Ryan), Kate & Leopold List slides 4. Travel back in time to an era without modern medicine, electronics, or equal rights for women: Kate McKay (Meg Ryan), Kate & Leopold 4. Travel back in time to an era without modern medicine, electronics, or equal rights for women: Kate McKay (Meg Ryan), Kate & Leopold In this slightly bizarre 2001 rom-com, Hugh Jackman’s 19th-century duke accidentally leaps forward in time to contemporary New York where he falls for Meg Ryan’s uptight businesswoman, Kate McKay. Kate & Leopold is eager to push the notion that the chivalrous past is far superior to the hectic present, which is why the movie climaxes with Kate’s decision to jump back through time to 1876 in order to marry Leopold. Of course, that gestures feels a little less heartwarming when one considers Kate is leaving behind her family, her friends, her career, modern medicine, and the Internet—all for a dude. And while she does get to spend the rest of her life with Jackman’s dashing Leopold (admittedly no small prize), Kate unfortunately has to give up the right to vote in the process. [Caroline Siede] Advertisement

6 / 30 5. Fly to London to “fight” for the woman you’ve only known for two weeks who said “thank you” after you told her you love her: Ross Geller (David Schwimmer), Friends List slides 5. Fly to London to “fight” for the woman you’ve only known for two weeks who said “thank you” after you told her you love her: Ross Geller (David Schwimmer), Friends 5. Fly to London to “fight” for the woman you’ve only known for two weeks who said “thank you” after you told her you love her: Ross Geller (David Schwimmer), Friends Ross Geller (David Schwimmer) is a hopeless romantic who’s very easily influenced, two traits that converge into one of his most desperate pursuits for love in a sitcom full of them. After a whirlwind two-week relationship with Emily (Helen Baxendale) from England, Ross decides to make a grand romantic gesture straight out of every clichéd rom-com: He races to the airport to tell Emily he loves her. She, startled, replies “thank you” and gets on the plane. Then she phones Ross to tell him there’s someone else she’s involved with and she needs time to figure things out. Goaded into action by the much stronger willed Monica (Courtney Cox), Ross flies to England like it’s no big deal to spend the time and money on a cross-Atlantic flight. Instead of calling her to tell her he’s coming, he waits outside her apartment building because he’s going to “fight for her.” It crosses into stalker territory, strengthened by the commitment to travel literally thousands of miles to stare at the building of the woman whose middle name he probably didn’t know. But this is Friends, so the situation is played for humor rather than a lesson on how not to stalk: Emily has done the same thing in reverse, returning to New York to tell Ross she loves him. [Caitlin PenzeyMoog] Advertisement

7 / 30 6. Construct a completely false identity: Prince Akeem (Eddie Murphy), Coming To America; Aladdin, Aladdin List slides 6. Construct a completely false identity: Prince Akeem (Eddie Murphy), Coming To America; Aladdin, Aladdin 6. Construct a completely false identity: Prince Akeem (Eddie Murphy), Coming To America; Aladdin, Aladdin Every relationship begins with a getting-to-know you phase, so why not get off on the right foot by insuring everything your new love knows about you is a lie? Few lovers have gone to as great lengths as Coming To America’s Prince Akeem, who uses his vast wealth to convince his new love interest he’s an impoverished student, keeping the ruse going until he’s satisfied that she’s not interested in money. Or honesty. The reverse works as well, as Aladdin’s hero pretends to be a wealthy prince to woo Princess Jasmine, who takes it surprisingly well when she learns he’s a homeless urchin. [Mike Vago] Advertisement

8 / 30 7. Break into song in the back of a kindergarten classroom, then slowly walk to the front, ignoring requests to stop: Nathan Huffner (Rick Moranis), Parenthood List slides 7. Break into song in the back of a kindergarten classroom, then slowly walk to the front, ignoring requests to stop: Nathan Huffner (Rick Moranis), Parenthood 7. Break into song in the back of a kindergarten classroom, then slowly walk to the front, ignoring requests to stop: Nathan Huffner (Rick Moranis), Parenthood The movie Parenthood is filled with adults and children alike struggling to figure out life and love, but no love is quite so disturbingly rendered as that between Nathan Huffner (Rick Moranis) and Susan Buckman (Harley Jane Kozak). After Susan leaves Nathan for being an overbearing, pompous ass who exhibits almost no redeeming qualities, he decides to win her back. The plan? Standing in the back of her classroom, waiting until a quiet moment, and then singing “Close To You” while slowly advancing on Susan, ignoring her requests that he stop. The film repeatedly cuts to a wide-eyed Moranis, off-key and moving with the implacable gait of a serial killer. Take away the pat resolution, and it’s a restraining order waiting to happen. [Alex McCown] Advertisement

9 / 30 8. Save the king’s life so he’ll force the object of your affections to marry you against his will; pretend to be another woman so he’ll have sex with you, thinking you’re her; fake your own death, then return to break up his wedding: Helena, All’s Well That Ends Well List slides 8. Save the king’s life so he’ll force the object of your affections to marry you against his will; pretend to be another woman so he’ll have sex with you, thinking you’re her; fake your own death, then return to break up his wedding: Helena, All’s Well That Ends Well Peter Glenville and Patricia Tucker in All’s Well That Ends Well at the Vaudeville Theatre, London, 1940 Photo : Gordon Anthony ( Getty ) 8. Save the king’s life so he’ll force the object of your affections to marry you against his will; pretend to be another woman so he’ll have sex with you, thinking you’re her; fake your own death, then return to break up his wedding: Helena, All’s Well That Ends Well Creepy behavior in the name of love has a long tradition, and William Shakespeare strained the title of All’s Well That Ends Well nearly to the breaking point with his heroine’s antics. Helena loves nobleman Bertram, who is above her station and doesn’t return her feelings. To win him over, she cures the king of France’s illness, and asks in return that his majesty force Bertram to marry her against his will. Bertram flees the country rather than stay with Helena, but she follows him, switching places with Bertram’s latest conquest so he sleeps with Helena unknowingly. She then fakes her own death, and a relieved Bertram proposes to another woman. Helena reappears in time to break up the wedding, and a psychologically shattered Bertram agrees to marry her instead, if only to make her stop. [Mike Vago] Advertisement

10 / 30 9. Trick her into loving someone else and lie about it after that guy dies so she spends the rest of her life as an unhappy widow: Cyrano, Cyrano De Bergerac List slides 9. Trick her into loving someone else and lie about it after that guy dies so she spends the rest of her life as an unhappy widow: Cyrano, Cyrano De Bergerac 9. Trick her into loving someone else and lie about it after that guy dies so she spends the rest of her life as an unhappy widow: Cyrano, Cyrano De Bergerac The fact that the bulbous-nosed poet Cyrano De Bergerac is in love with his own cousin Roxane is actually the least creepy thing about this classic play by Edmond Rostand. Convinced she could never see past his unsightly feature, Cyrano agrees to help his dunderheaded friend, Christian De Neuvillette, earn her hand in marriage by providing the intellect needed to woo the brilliant Roxane. Yet even that isn’t as creepy as the fact that once Christian dies in battle, Cyrano decides the best way to honor his friend’s memory is to keep up the charade, thus forcing Roxane into an unhappy, celibate life at a convent for 15 years. In the end, Cyrano dies from a freak log accident just moments after Roxane figures out he’s the one she’s really in love with, leaving all parties either miserable or dead for absolutely no reason. The play is meant to be beautifully tragic, but it works far better as an argument against 17th century catfishing. [Caroline Siede] Advertisement

11 / 30 10. Write an ostensibly romantic song that is actually a straight-up stalker confessional: Unnamed narrator, “Every Breath You Take,” The Police List slides 10. Write an ostensibly romantic song that is actually a straight-up stalker confessional: Unnamed narrator, “Every Breath You Take,” The Police 10. Write an ostensibly romantic song that is actually a straight-up stalker confessional: Unnamed narrator, “Every Breath You Take,” The Police When it came out in 1983, The Police’s “Every Breath You Take” topped the charts in both the U.S. and U.K., making it the biggest hit of that year. It appeared on the band’s final album, Synchronicity, which sold in excess of 10 million records. Did anybody even listen to the lyrics? What sounds like a sweet melody and gentle love song is actually a forthright stalker confessional inspired by Sting’s divorce from Frances Tomelty. Even Sting says that the song is “very, very sinister.” No kidding: With lyrics like “every breath you take / I’ll be watching you” and “can’t you see / you belong to me,” there’s not much nuance here, yet it is apparently still a common request for wedding songs. Good luck with that marriage. [Laura M. Browning] Advertisement

12 / 30 11. Agree to kill your best friend in a duel: Benedick, Much Ado About Nothing List slides 11. Agree to kill your best friend in a duel: Benedick, Much Ado About Nothing 11. Agree to kill your best friend in a duel: Benedick, Much Ado About Nothing Much Ado About Nothing remains perhaps Shakespeare’s most satisfying romance because despite their insistence that they hate each other, Beatrice and Benedick are clearly perfect together. But it’s not until Benedick’s best friend Claudio viciously slanders Beatrice’s innocent friend Hero that the warring duo finally builds up the courage to confess their love. Of course, all that joy is cut short when Beatrice demands Benedick kill Claudio for her. In a moment that’s both slightly creepy and a great example of a Shakespearean hero believing the word of a woman over that of a man, Benedick agrees to engage his best friend in a duel to the death. Since it’s a comedy, things work out okay in the end, but Benedick’s willingness to literally fight for Beatrice remains both disturbing and kind of sweet. Even Tom Hiddleston agrees. [Caroline Siede] Advertisement

13 / 30 12. Completely toss your persona to remake your image into your boyfriend’s ideal babe in black leather: Sandy (Olivia Newton-John), Grease List slides 12. Completely toss your persona to remake your image into your boyfriend’s ideal babe in black leather: Sandy (Olivia Newton-John), Grease 12. Completely toss your persona to remake your image into your boyfriend’s ideal babe in black leather: Sandy (Olivia Newton-John), Grease Grease’s Sandy Olsson (Olivia Newton-John) was a sweet-faced and -voiced Australian transplant who knew how to rock a sweater set and put her hair in any number of elaborate ponytails or updos. Within moments of arriving at Rydell High, she had already made the cheerleading squad and had the star quarterback eating out of her hand. She even inspired notorious Thunderbird Danny Zuko (John Travolta) to contemplate a high-school commitment. So why would Sandy tell her friend Frenchy that she’s not happy, but the only way she can be is to doll herself up in black leather and spandex and red mules? With a horrific opening line (“Tell me about it… stud”), Sandy transforms her entire persona into a Rizzo wannabe instead of the fresh-faced girl Danny fell for. Danny readily and unfortunately embraces the new Sandy, striking a blow to sweater-set sincerity. [Gwen Ihnat] Advertisement

14 / 30 13. Secretly film someone inside their bedroom, then spell their name out in fire beneath her window: Ricky Fitts (Wes Bentley), American Beauty List slides 13. Secretly film someone inside their bedroom, then spell their name out in fire beneath her window: Ricky Fitts (Wes Bentley), American Beauty 13. Secretly film someone inside their bedroom, then spell their name out in fire beneath her window: Ricky Fitts (Wes Bentley), American Beauty Was ever there a more disturbing kid painted as a sweet romantic than American Beauty’s Ricky Fitts (Wes Bentley)? First, he films poor Jane (Thora Birch) through her window; next, her stares her down at school with the force of a thousand Mark David Chapmans. But after calling him out for filming her, our budding young sociopath—rather than stop—spells out her name in flames on the ground one night, and resumes filming her reaction. The movie may capture the angst-filled uncertainty of young romantic impulses, but it also shows that kids can easily mistake danger signs for flowers. Run, Jane, run! [Alex McCown] Advertisement

15 / 30 14. Cancel your wedding to a guy after you tricked his whole family into thinking you were his fiancée while he was in a coma: Lucy Moderatz (Sandra Bullock), While You Were Sleeping List slides 14. Cancel your wedding to a guy after you tricked his whole family into thinking you were his fiancée while he was in a coma: Lucy Moderatz (Sandra Bullock), While You Were Sleeping 14. Cancel your wedding to a guy after you tricked his whole family into thinking you were his fiancée while he was in a coma: Lucy Moderatz (Sandra Bullock), While You Were Sleeping There are very few things about While You Were Sleeping that aren’t creepy. Lucy Moderatz (Sandra Bullock) is an unhappy public transportation worker with a big crush on a handsome commuter named Peter Callaghan (Peter Gallagher). So when she rescues him from a near-death accident and he winds up in a coma, she naturally tricks his big, loving family into thinking she’s his fiancée. But really that’s all just setup for the film’s real love story between Lucy and Peter’s brother Jack (Bill Pullman). Then things get really weird when Peter wakes up and his family pressures him into marrying Lucy despite having no memory of her. Eventually Lucy does stop the wedding, but only to confess her love for Jack while simultaneously dumping his brother. In the end, despite the fact that she pulled an incredibly creepy long con on his whole family, Jack proposes to Lucy anyway, proving Bullock’s charms can overcome just about any obstacle. [Caroline Siede] Advertisement

16 / 30 15. Instantly decide a woman walking by is “the one” even though you can’t tell her apart from other women walking by, then become her teacher so you can exploit the power imbalance to insinuate yourself into her life: Adrian Cronauer (Robin Williams), Good Morning, Vietnam List slides 15. Instantly decide a woman walking by is “the one” even though you can’t tell her apart from other women walking by, then become her teacher so you can exploit the power imbalance to insinuate yourself into her life: Adrian Cronauer (Robin Williams), Good Morning, Vietnam 15. Instantly decide a woman walking by is “the one” even though you can’t tell her apart from other women walking by, then become her teacher so you can exploit the power imbalance to insinuate yourself into her life: Adrian Cronauer (Robin Williams), Good Morning, Vietnam Good Morning, Vietnam is certainly in the top half of Robin Williams’ filmography, but it’s an odd confluence of elements—a feel-good comedy about Williams’ hyperactive Armed Forces Radio DJ Adrian Cronauer, a wrenching war drama about trust and betrayal, and a language barrier-impaired romantic comedy. In his first hour in the country, Cronauer spots a woman (Chintara Sukapatana) walking by and decides to win her over, despite not being able to tell her apart from the very next woman who walks by (because they all look alike! Get it?!). He makes the obvious romantic gesture—bribing someone so he can become her English teacher, and then exploiting his authority to get to know her better. Probably for the best he gets shipped out in the end. [Mike Vago] Advertisement

17 / 30 16. Ambush your crush in your basement with an impromptu rendition of “Lady”: Nick Andopolis (Jason Segel), Freaks And Geeks List slides 16. Ambush your crush in your basement with an impromptu rendition of “Lady”: Nick Andopolis (Jason Segel), Freaks And Geeks 16. Ambush your crush in your basement with an impromptu rendition of “Lady”: Nick Andopolis (Jason Segel), Freaks And Geeks Nick Andopolis (Jason Segel) and Lindsay Weir (Linda Cardellini) were doomed from the start. What started as a Lindsay-initiated pity kiss immediately turned into a full-fledged obsession for pot-addled Nick. The most cringeworthy moment in their relationship is when Nick corners Lindsay in his dingy basement, lit with enough candles for a satanic ritualistic homicide, and nervously speak-sings Styx’s power balled “Lady” to her. Let’s look at the myriad ways in which this creepy romantic gesture failed: a) At no point in history has it ever been cool, hip, or sexy to sincerely serenade a woman (or anyone) to “Lady.” b) Nick professes his love and commitment far too soon, when they are only in the incubation stage of their dating. c) He chooses to perform in his dank basement, where his militant father could pop downstairs at any time. Everything about it is misguided, but also sweet in its own heartfelt way, which sums up Nick Andopolis perfectly. [Drew Fortune] Advertisement

18 / 30 17. Hire a prostitute, then paternalistically try to take care of her: Edward Lewis (Richard Gere), Pretty Woman List slides 17. Hire a prostitute, then paternalistically try to take care of her: Edward Lewis (Richard Gere), Pretty Woman 17. Hire a prostitute, then paternalistically try to take care of her: Edward Lewis (Richard Gere), Pretty Woman Pretty Woman wants to have its cake and eat it too when it comes to questionable romantic gestures. Throughout the movie rich businessman Edward Lewis (Richard Gere) is obsessed with helping spunky prostitute Vivian Ward (Julia Roberts) revamp her life, which mostly means giving her money to buy new clothes, hang out with him, and have sex whenever he wants. Though the film occasionally questions the imbalance of the relationship (one person paying the other for sex is perhaps not the best way to start an equal partnership) and Vivian makes some stabs at independence, in the end all she wants is a knight on a white horse (or limo) to sweep her off her feet, which Edward is only too happy to provide. When it comes to depicting gender equality, Pretty Woman made a big mistake. Big. Huge. [Caroline Siede] Advertisement

19 / 30 18. Reveal your feelings in a national newspaper and challenge the object of your affection to kiss you for the first time in a baseball field in front of thousands: Josie Geller (Drew Barrymore), Never Been Kissed List slides 18. Reveal your feelings in a national newspaper and challenge the object of your affection to kiss you for the first time in a baseball field in front of thousands: Josie Geller (Drew Barrymore), Never Been Kissed 18. Reveal your feelings in a national newspaper and challenge the object of your affection to kiss you for the first time in a baseball field in front of thousands: Josie Geller (Drew Barrymore), Never Been Kissed This 1999 teen rom-com has everything: clique wars, prom humiliation, and an illicit student-teacher flirtation between Josie the undercover reporter (Drew Barrymore), and Sam the impossibly cute English teacher (Michael Vartan). When Josie blows her cover, though, she decides to devote the column she had been researching for months at this high school to apologizing for not coming clean to the teacher she was flirting with. She then goes on to say that if he wants to move on from this incident, she’ll be waiting to kiss him on the pitcher’s mound of a baseball stadium—and then we cut to her anxiously waiting there, surrounded by bright lights, camera crews, and thousands of people. Both Chicago and Sam end up enraptured by the romance of this moment, but in reality, this is an ambush that puts a hell of a lot of pressure on one kiss. [Caroline Framke] Advertisement

20 / 30 19. Meticulously construct an entire day’s worth of conversation in order to win someone over: Phil Connors (Bill Murray), Groundhog Day List slides 19. Meticulously construct an entire day’s worth of conversation in order to win someone over: Phil Connors (Bill Murray), Groundhog Day 19. Meticulously construct an entire day’s worth of conversation in order to win someone over: Phil Connors (Bill Murray), Groundhog Day Once weatherman Phil Connors gets the hang of Groundhog Day’s premise—that he’s trapped reliving February 2 over and over—he decides to play things to his creepy advantage, going on date after date with Rita (Andie MacDowell), rewriting the script every time he says the wrong thing. It takes innumerable repetitions before Phil realizes there’s no magical combination of words that will win her over, and that only by making himself a better person does he get the girl and break out of the time loop. Of course, the movie glosses over whether two people with so little in common should end up together in the first place. [Mike Vago] Advertisement

21 / 30 20. Commit yourself to a never-ending war on evil in order to impress a pretty 15-year-old: Angel (David Boreanaz), Buffy The Vampire Slayer List slides 20. Commit yourself to a never-ending war on evil in order to impress a pretty 15-year-old: Angel (David Boreanaz), Buffy The Vampire Slayer 20. Commit yourself to a never-ending war on evil in order to impress a pretty 15-year-old: Angel (David Boreanaz), Buffy The Vampire Slayer Buffy The Vampire Slayer never shied away from the potential unhealthiness of its hero’s relationships with centuries-old dead dudes, especially after a coupling between a just-17-year-old Buffy and her vampire lover, Angel, sent the latter on a soulless killing spree. The resolution to that arc has a moment that’s a lot less beautiful and sweet than the show seems to think: A flashback to the first time Angel ever saw his beloved, skeevily watching her from across a parking lot as Tom from Office Space revealed her vampire-slaying destiny. It marks the moment when Angel turns from a traumatized bystander, haunted by the crimes of his past, to the man who would eventually face down a demonic army in a rainy Los Angeles alley, all thanks to his crush on a 15-year-old girl he’d never even talked to. You can say whatever you like about how he was recognizing Buffy’s inner fire or responding to her sudden forced maturity: Fact remains, one of TV’s iconic love stories, and Angel’s personal crusade against the forces of darkness, got their start with a filthy old murderer perving on a high school freshman sucking a lollipop in a mid-thigh pencil skirt. [William Hughes] Advertisement

22 / 30 21. Hire a professional ladies man to help you romance a crush via information obtained through stalking: Albert Brennaman (Kevin James); anyone else who hires Alex “Hitch” Hitchens (Will Smith), Hitch List slides 21. Hire a professional ladies man to help you romance a crush via information obtained through stalking: Albert Brennaman (Kevin James); anyone else who hires Alex “Hitch” Hitchens (Will Smith), Hitch 21. Hire a professional ladies man to help you romance a crush via information obtained through stalking: Albert Brennaman (Kevin James); anyone else who hires Alex “Hitch” Hitchens (Will Smith), Hitch In Hitch, Will Smith plays a consultant who goes by the moniker “Hitch,” since his business is helping meek men land the hot women they’re otherwise too scared to approach. Hitch’s method involves smooth talking, bland dancing, and oh yeah, using personal information about these women to fake compatibility. Despite the movie’s attempt to give Hitch a moral code (he only helps men “in love”), his tips still come off as creepy as any pickup artist’s—especially because, again, there is always some light-to-moderate stalking involved. Still, the creepiest part may be when Hitch passionately yells, “I help women get out of their own way!” The movie sees this as a heroic moment of truth, when really, it’s a reason to back away slowly. [Caroline Framke] Advertisement

23 / 30 22. Spend your one day on leave in New York City chasing a girl you’ve never met all over town based on her “Miss Turnstiles” poster: Gabey (Gene Kelly), On The Town List slides 22. Spend your one day on leave in New York City chasing a girl you’ve never met all over town based on her “Miss Turnstiles” poster: Gabey (Gene Kelly), On The Town 22. Spend your one day on leave in New York City chasing a girl you’ve never met all over town based on her “Miss Turnstiles” poster: Gabey (Gene Kelly), On The Town Perhaps the need for mid-century movie musicals to rely on songs and dances meant that these movies often had to take abrupt and seemingly insane shortcuts to romance. In the otherwise-awesome On The Town, Gabey (Gene Kelly) and his two Navy pals get one 24-hour leave in New York City. Will Gabey spend the day seeing the sights, like his wise pal Chip (Frank Sinatra)? Or will he blow his entire single day of leave chasing a girl called Miss Turnstiles (Vera-Ellen) after spotting her briefly in the subway? At least the chase leads Gabey and his friends to some of the sights, like museums and nightclubs, but it seems like a hell of a waste of precious free time—and a rather unhinged way to kick off a relationship. Gabey’s senseless rationale: “You know, somewhere in the world there’s a right girl for every boy. I guess I found the one for me before I even met you.” [Gwen Ihnat] Advertisement

24 / 30 23. Fall in love “at first sight” and basically stalk a young French woman until she agrees to spend her life with you: Jerry (Gene Kelly), An American In Paris List slides 23. Fall in love “at first sight” and basically stalk a young French woman until she agrees to spend her life with you: Jerry (Gene Kelly), An American In Paris 23. Fall in love “at first sight” and basically stalk a young French woman until she agrees to spend her life with you: Jerry (Gene Kelly), An American In Paris A few years later, we find the undaunted Gene Kelly instantly besotted again, this time with French shopgirl Lise (Leslie Caron in her film debut). Based on love at first sight, his character Jerry does what in this day and age would get him slapped with a restraining order: constantly pestering a perfect stranger who has no interest in him, who tries to thwart him with a wrong phone number, and even tells him to leave her alone, for God’s sake. Somehow Jerry’s assist with a fragrance sale and some goofball antics with perfume bottles are enough to change young Lise’s mind, unfortunately setting a blueprint for decades of undesired suitors. At least the movie’s Gershwin songs are still spectacular. [Gwen Ihnat] Advertisement

25 / 30 24. Fly cross-country, dig up parks, and generally tear everything up searching for your ex’s locket because it would make the perfect “you should be with me” present for her wedding to your close friend: Ted Mosby (Josh Radnor), How I Met Your Mother List slides 24. Fly cross-country, dig up parks, and generally tear everything up searching for your ex’s locket because it would make the perfect “you should be with me” present for her wedding to your close friend: Ted Mosby (Josh Radnor), How I Met Your Mother 24. Fly cross-country, dig up parks, and generally tear everything up searching for your ex’s locket because it would make the perfect “you should be with me” present for her wedding to your close friend: Ted Mosby (Josh Radnor), How I Met Your Mother Ted Mosby (Josh Radnor) is a huge fan of the grand romantic gesture. From stealing an instrument from a first date restaurant, to attending the same Halloween party in the same Halloween costume time and again to find a girl he met years ago, Ted believes that the bigger the gesture, the better the sentiment. This tended to work out for him, even toward the end of the series when his romantic inclinations escalated to the point that he actually flew across the country in search of a locket. Also, the locket was for his ex, Robin, on the eve of her wedding to his close friend. When the cross-country trip proved fruitless, he re-traced Robin’s steps to such an obsessive degree that he did eventually find the necklace, but not before raising a whole mess of red flags—just not for anyone on the show. [Caroline Framke] Advertisement

26 / 30 25. Stand outside your ex’s window, holding a boom box over your head, blasting the song that was playing when you first slept with her: Lloyd Dobler (John Cusack), Say Anything… List slides 25. Stand outside your ex’s window, holding a boom box over your head, blasting the song that was playing when you first slept with her: Lloyd Dobler (John Cusack), Say Anything… 25. Stand outside your ex’s window, holding a boom box over your head, blasting the song that was playing when you first slept with her: Lloyd Dobler (John Cusack), Say Anything… One of the most iconic images of teenage romance from the ’80s also doubles as the very picture of creepy. In Cameron Crowe’s 1989 romance Say Anything… young Lloyd Dobler (John Cusack) and Diane Court (Ione Skye) fall in love, but the path to end-of-film togetherness must hit a few hurdles along the way. At one point, Diane breaks up with Lloyd, and as part of his campaign to win her back, he stands outside her window while she tries to sleep, holding up a boom box, blasting Peter Gabriel’s “In Your Eyes”—the song playing when they first had sex. Imagine a guy you broke up with appearing at your house during the night, blaring music, and refusing to leave: Yeah, exactly. [Alex McCown] Advertisement

27 / 30 26. Go to your best friend’s house to silently stand in front of the door while holding up signs declaring your love for your best friend’s wife while Christmas carols play: Mark (Andrew Lincoln), Love Actually List slides 26. Go to your best friend’s house to silently stand in front of the door while holding up signs declaring your love for your best friend’s wife while Christmas carols play: Mark (Andrew Lincoln), Love Actually 26. Go to your best friend’s house to silently stand in front of the door while holding up signs declaring your love for your best friend’s wife while Christmas carols play: Mark (Andrew Lincoln), Love Actually In the real world—or a world with better screenwriters—the logistics alone would have stopped this famous scene before it had begun. What if Juliet’s husband Peter had answered the door when his best friend Mark knocked? What if he came to the door after his wife didn’t return? What if Juliet realized her husband was kind of an asshole after he told Christmas carolers to “bugger off”? But the world of Love, Actually is tailor-made for outrageous displays of love, so Mark sets his boom box to play “Silent Night” (which does not in any way sound like carolers) and produces his signs. That Juliet plays along is problematic in a different way, as it comes after the scene in which she discovers the wedding video Mark shot is literally only of her. Despite discovering this classic stalker practice, Juliet smiles and giggles through Mark’s declaration of love, running after him to give him a kiss on the lips. “Enough. Enough now,” Mark says and walks out of frame, like it’s a big cathartic release for him and he can move on after his unrequited love kisses him. Love may actually be all around us, but in this film it seems love only comes with an unhealthy dose of unrealized creepiness. [Caitlin PenzeyMoog]

And that’s not the only Love, Actually moment deserving of a spot on this list...


28 / 30 27. Learn Portuguese to propose to your maid who you’ve never really spoken with and have only known for a few weeks: Jamie (Colin Firth), Love, Actually List slides 27. Learn Portuguese to propose to your maid who you’ve never really spoken with and have only known for a few weeks: Jamie (Colin Firth), Love, Actually 27. Learn Portuguese to propose to your maid who you’ve never really spoken with and have only known for a few weeks: Jamie (Colin Firth), Love, Actually A lot of Love, Actually hinges on the love story between bumbling writer Jamie (Colin Firth) and his shy but beautiful housekeeper Aurélia (Lúcia Moniz), which earns the final slot in the film’s climactic montage. And while it’s sweet that Jamie learns Portuguese (and Aurélia learns English) in order to better facilitate their awkward flirting, it’s really weird that they wind up getting engaged after knowing each other for only a few weeks (especially considering Jamie met Aurélia just days after finding his longtime girlfriend cheating with his brother). “I know I seems an insane person because I hardly knows you,” Jamie says in broken Portuguese, “but sometimes things are so transparency they don’t need evidential proof.” That may be true, but going on a date before agreeing to get married doesn’t hurt either. [Caroline Siede] We’re still not done with Love, Actually... Advertisement