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If you asked a random single woman about her dream proposal, there’s a good chance it would include her own Mr. Darcy — or at the very least, her own Mark Darcy. The problem with those unrealistic expectations set by pop culture? Sorry to be the bearer of bad news, but you are not Matthew Macfadyen or Colin Firth, and real life is much messier than romantic comedies would have you believe.
That’s not to say there’s nothing to be gleaned from the film and TV proposals that have made their way into the cultural lexicon. In fact, whether we’re talking about Adam Sandler’s unforgettable airplane performance in The Wedding Singer or Billy Crystal’s quasi-proposal on New Year’s Eve in When Harry Met Sally, there are lessons galore that can help men nail what should be one of the biggest and happiest moments of their lives.
Below, we’ve rounded up 17 of the most memorable on-screen proposals, from successes to disasters, and the wisdom you should take from them.
Pride & Prejudice (2005)
Lesson: Tell her how you feel
It sounds like a no-brainer, but it’s easy to be too distracted by logistics or too focused on getting the big question out to remember that at the end of the day, a proposal is a declaration of love — eternal love, assuming things go according to plan. Don’t forget to take some time before you officially pop the question to tell your soon-to-be fiancée how much she means to you. And if you’re not entirely sure how to put it into words, you can always pull inspiration from Mr. Darcy (Matthew Macfadyen) and his iconic line: “You have bewitched me, body and soul.”
When Harry Met Sally (1989)
Lesson: Don’t drag your feet
Sure, Harry (Billy Crystal) doesn’t actually utter the words “Will you marry me?” at that fateful New Year’s Eve party in When Harry Met Sally, but the movie’s ending confirms that he and Sally (Meg Ryan) do, in fact, wind up getting hitched. After delivering one of the greatest rom-com speeches of all time, rattling off all the things he loves about her (including “that you get cold when it’s 71 degrees out” and “that you get a little crinkle above your nose when you’re looking at me like I’m nuts”), Harry closes with something to keep in mind when deciding when to propose: “When you realize you want to spend the rest of your life with somebody, you want the rest of your life to start as soon as possible.” So don’t fret too much over timing. If you know, you know.
Love Actually (2003)
Lesson: Meet them halfway
Realistically, would two people who don’t speak the same language — living in a pre-Google Translate world — and whose communication is limited to hand gestures, meaningful looks and general vibes be able to get to know each other well enough to decide that they’re in love? Probably not. But if we suspend disbelief, Jamie’s (Colin Firth) proposal to Aurelia (Lúcia Moniz) in Love Actually is pretty heartwarming: He shows up at her village unannounced, finds her at work and reveals that he learned Portuguese by asking for her hand in marriage in her native tongue. The kicker? She responds in English, meaning each of them secretly went out of their way to learn the other’s language. The lesson here is that marriage is about meeting each other halfway — and that same advice can be applied to the proposal itself. If you’ve got your heart set on popping the question on the Jumbrotron at a Knicks game but know that she hates being the center of attention, maybe try splitting the difference and taking her out to a nice dinner instead.
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The Wedding Singer (1998)
Lesson: If you’re going to make a grand gesture, be sure it’s a good one
Planning a big public proposal? It’s important that you understand the risk of humiliation is high. If you’re going to be singing or reading a poem or anything else with the potential for embarrassment, you’d better be confident it’s going to be good. You don’t want your fiancée quietly cringing through your proposal, and you certainly don’t want to inspire some bystander to whip out their phone and turn you into a meme. The grand-gesture benchmark should always be Robbie (Adam Sandler) serenading Julia (Drew Barrymore) on the airplane in The Wedding Singer. It would be extremely cheesy in lesser hands, but he absolutely crushes it with “I Wanna Grow Old With You.” Make sure to practice in front of an audience you trust who can give honest feedback (and who can keep a lid on it).
Sweet Home Alabama (2002)
Lesson: Bigger isn’t always better
Look, would I be mad if someone proposed to me by taking me to a rented-out Tiffany showroom, getting down on one knee and saying, “Pick one”? Absolutely not. But this Sweet Home Alabama moment is a good reminder that not every on-screen proposal has a happy ending. Andrew (Patrick Dempsey) is not the hero of this rom-com, but rather the guy standing in the way of our two protagonists’ happily ever after. Melanie (Reese Witherspoon) says yes in the moment, but she ultimately realizes her heart belongs to another man back in the small town she grew up in. You can have all the money in the world, but if you’re not the right person, that gigantic diamond is meaningless.
Bridget Jones: The Edge of Reason (2004)
Lesson: Be confident in your “yes”
One of the core personality traits of Bridget Jones (Renée Zellweger) is that she’s constantly putting her foot in her mouth, so it’s fitting that when Mark Darcy (Colin Firth) starts his proposal with “There’s a question I’ve been meaning to ask you,” she responds by jokingly saying, “All right, as long as it’s not ‘Will you marry me?’” It all works out for them in the end: Bridget realizes she was, in fact, about to be proposed to and requests a do-over. But it’s a good reminder that it’s important to be certain that your partner actually wants to get engaged to you before popping the question. If you’re unsure, that’s your answer — it’s too soon.
New Girl (2015)
Lesson: Don’t be afraid of a good callback
Schmidt (Max Greenfield) and Cece (Hannah Simone) had an on-again, off-again situation going on for much of the run of New Girl, but when they finally wound up together for good, the show took us all the way back to the beginning, revealing that Schmidt had kept the five-dollar bill he deposited into the group’s “Douchebag Jar” for saying, “Girl, I’mma marry you” to her the day they met in Season 1. With that five in hand, he gets down on one knee and asks, “Girl, will you marry me?” You don’t need to have a Douchebag Jar of your own to incorporate something similar into your proposal. Surely you and your significant other have some sort of inside joke or a recurring bit that might be fun to add. Even if you don’t, you can always work in a little nostalgia and do something sentimental like return to the site of your first date.
Serendipity (2001)
Lesson: Pack it in, pack it out
Before she realizes she’s in love with the guy she serendipitously met in a department store, Sara (Kate Beckinsale) gets this well-intentioned proposal from her boyfriend Lars (John Corbett). When she walks into her home, there are rose petals all over the floor and a giant box with a bow and a note that says “Open me!!” She does, and finds…another, slightly smaller box, which contains another and another until finally she’s holding an empty ring box. Lars appears, holding the ring, and says, “You’ve gotta say yes first.” It’s all very sweet, but what’s not shown is just as essential as what is. Cleaning up a mess is not my idea of romance, so if you go this route, be prepared to tidy up afterwards. Now that is husband material.
My Big Fat Greek Wedding (2002)
Lesson: Know what style of proposal your partner prefers
Our second John Corbett proposal on this list is much less labor-intensive. In My Big Fat Greek Wedding, Toula (Nia Vardalos) and Ian (Corbett) are simply snuggling in bed when he eventually says, “I love you. I don’t know how to say this…will you marry me?” And that’s it. No elaborate surprise, no grand declarations, no getting down on one knee — just a sweet, private moment between the two of them. Not everyone wants or needs their engagement to be a big event. (If you don’t already know where your partner falls, you probably shouldn’t be marrying them.) At the end of the day, it’s the idea behind the proposal that matters.
Grey’s Anatomy (2012)
Lesson: Don’t be afraid to bail out if the vibe isn’t right
In Season 8 of Grey’s Anatomy, the engagement of anesthesiologist Ben Warren (Jason Winston George) and Dr. Miranda Bailey (Chandra Wilson) starts with a fight. Ben has spent two months putting together a custom crossword puzzle — mocked up to look like the one in The New York Times and everything — with clues related to their relationship. The only problem? Miranda didn’t bother to finish it because she was distracted by a big surgical case, so she never got to the central answer of the puzzle: the 14-letter phrase “Will you marry me?” It eventually works out for them when she finishes it in the operating room while performing a spinal surgery to remove a rare “bone-eating parasite,” but it’s a good example of why it’s important to read the room before you pop the question. Even the strongest couples fight occasionally, and if the energy is off, you can always punt to a later date. No one wants to look back at their proposal and remember how annoyed they were before it.
The Proposal (2009)
Lesson: Make sure you’re doing it for the right reasons
This Ryan Reynolds/Sandra Bullock rom-com features a classic enemies-to-lovers plot: Margaret (Bullock) is an overbearing boss from Canada who runs into some trouble with her visa and essentially forces her long-suffering personal assistant Andrew (Reynolds) into marrying her so she can get a green card. Naturally, an immigration officer suspects them of fraud, leaving Margaret no choice but to agree to give Andrew a promotion in exchange for his pretending to be in a relationship with her. You can probably see where this is going: Somewhere along the way, they wind up falling in love, and Andrew eventually proposes for real, to keep her in the country and give them the opportunity to be together. “You can imagine my disappointment when it suddenly dawned on me that the woman I love is about to be kicked out of the country,” he says. “So Margaret, marry me. Because I’d like to date you.”
Parks and Recreation (2012)
Lesson: Don’t rush the moment
Nerves and emotions are running high, so it makes sense that a lot of proposals are pretty quick. But when Ben (Adam Scott) starts to propose to Leslie (Amy Poehler) in the home they’re considering buying together, she cuts him off. He tries to restart, and she shuts him down again. “Hold on,” she says. “I need another second, please. I need to remember every little thing about how perfect my life is right now at this exact moment.” In an ideal world, you only propose to someone once in your life. Take a second (or two) to soak it all in.
Crazy Rich Asians (2018)
Lesson: You don’t need family approval, but it’s nice when you can get it
It shouldn’t matter whether your family approves of your relationship or not as long as you’re in love. That’s the realization Nick (Henry Golding) comes to before he finds a way onto Rachel’s (Constance Wu) flight, where he presents her with a ring. But it’s not just any ring; it’s his mother’s, meaning she’s finally come around to Rachel, the former object of her ire. Understand that family approval isn’t necessary — many people have rough or complicated relationships with their parents — but it is a nice thing if you can get it. You don’t have to ask for permission to marry their daughter, but a heads-up before you pop the question is a nice courtesy.
Schitt’s Creek (2019)
Lesson: Know your partner’s ring preferences
There’s a lot about Patrick’s (Noah Reid) proposal to David (Dan Levy) in Season 5 of Schitt’s Creek that doesn’t go according to plan: he injures his foot on their hike, and David has to carry him up to the summit. Worried that the moment is ruined, he’s hesitant to go through with it, but David insists on setting up the romantic picnic they had planned. (“I didn’t carry you up a mountain not to eat cheese after,” he says.) When Patrick tells him to go into the front pocket of his backpack for him, David finds the one aspect of this proposal that was executed flawlessly: a box of four gold rings, to match the set of four silver ones he wears all the time on his right hand. Save yourself from an awkward conversation later and make sure you know what kind of jewelry your partner typically wears. (Or what they don’t wear: I have a friend whose now-husband knew she never wore rings, so he proposed to her with a Ring Pop instead.)
Walk the Line (2005)
Lesson: Don’t rely on peer pressure
Okay, sure, this onstage proposal from Johnny Cash to June Carter worked (in Walk the Line, but also in real life). But that doesn’t mean it’s something to emulate. The Man in Black (Joaquin Phoenix) had already asked June (Reese Witherspoon) to marry him — and been turned down multiple times when he paused in the middle of singing “Jackson” with her and proposed. She laughed it off and tried to get him to keep singing, but he continued, “Sorry, folks, but I just can’t do this song anymore unless she’s going to marry me…I’ve asked you 40 different ways, and it’s time you come up with a fresh answer.” She eventually said yes, and they were married for 35 years, until her death in 2003. But just because it worked out for them doesn’t mean you should consider turning your proposal into a low-stakes hostage situation and use a crowd of 7,000 people to pressure your significant other into saying yes. You are not Johnny Cash.
Moonstruck (1987)
Lesson: It’s okay to improvise
For every meticulously planned proposal, there’s another impromptu, heat-of-the-moment one, where someone suddenly finds themselves struck by how in love they are and simply blurts out, “Will you marry me?” That’s the case at the end of Moonstruck, when Johnny (Danny Aiello) returns unexpectedly from his trip to Italy and breaks off his engagement to Loretta (Cher). She angrily tosses her ring at him, and his brother Ronny (Nicolas Cage) — who she’s fallen in love with while Johnny was gone — pops up from his seat, asks Johnny if he can borrow the ring and pops the question. Everybody wins!
Shrinking (2023)
Lesson: If you’re going to enlist the help of other people, make sure they can deliver
Season 1 of Shrinking finds Jimmy (Jason Segel) in a particularly self-destructive phase as he struggles to cope with the recent and sudden death of his wife. His best friend Brian (Michael Urie) asks him to help him propose to his boyfriend, Charlie (Devin Kawaoka). The plan is to tell Charlie that Jimmy’s having a party to celebrate receiving an award at work, then have Jimmy play piano while Brian sings “You Are So Beautiful” to reveal that it’s actually a surprise engagement party. Instead, Jimmy gets drunk because he’s still grieving his dead wife and starts singing along with Brian — in a hilariously accurate Joe Cocker voice, no less — before projectile vomiting all over the piano. Fortunately, Charlie still says yes. But if you’re planning on asking a friend for help in executing your proposal, make sure you’re tasking them with something they can handle so there are no hiccups (or in this case, full-on barfs) along the way.
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