What Men Can Learn From 17 Unforgettable On-Screen Proposals

Welcome to The Groom’s Guide, our expert-led handbook designed to help you navigate the proposal, the wedding, and everything in between. 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.

Focus Features 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.”

Columbia Pictures 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 moment is still iconic. The takeaway here is that sometimes, the act of committing to someone—even if not explicitly through a proposal—can be just as meaningful. If you’re considering a more low-key approach, this scene suggests that showing your intent and dedication can be powerful in its own way.

Warner Bros. The Proposal (2009)

Lesson: Be prepared for spontaneity

In this romantic comedy, Sandra Bullock’s character, Margaret, is forced to marry her Canadian liaison, Andrew (Ryan Reynolds), to avoid deportation. The proposal happens in a public bathroom, of all places. This unexpected setting might seem like a disaster, but it also shows that being ready for anything—and making the most of the moment—can lead to a memorable proposal. If spontaneity isn’t your style, at least this one reminds us that life is unpredictable, and sometimes, the best moments happen when we least expect them.

Paramount Pictures The Notebook (2004)

Lesson: Create a personalized moment

The proposal in The Notebook is both intimate and filled with personal history. Ryan Gosling’s character, Noah, recreates a scene from the book “The Notebook” that they had shared as teenagers. This not only shows thoughtfulness but also ties their love story together, making the proposal feel like a natural progression of their relationship. Consider incorporating elements that are meaningful to both of you to make the moment feel uniquely special.

20th Century Fox The Wedding Singer (1998)

Lesson: Be yourself

Adam Sandler’s character, Rob, is a womanizing singer who proposes to his love interest, Julia (Drew Barrymore), mid-airplane flight. The proposal is unconventional and over-the-top, but it’s also genuine. This scene reminds us that being authentic and true to yourself can make even the most outlandish proposal memorable. If you’re not the type to recite a prepared speech, this one shows that spontaneity and being yourself can be the best proposal strategy of all.

Focus Features The Proposal (2009)

Lesson: Don’t be afraid to be silly

In this romantic comedy, Margaret (Sandra Bullock) and Andrew (Ryan Reynolds) end up in a public bathroom for an impromptu proposal. Andrew’s proposal is both heartfelt and humorous, showing that a little humor can diffuse tension and make the moment more enjoyable for both of you. If you’re worried about the pressure of the moment, consider incorporating a light-hearted element to keep things fun and relaxed.

Warner Bros. The Holiday (2006)

Lesson: Surprise her with a thoughtful gesture

In The Holiday, Graham (Jude Law) surprises Iris (Kate Winslet) with a proposal in a snowy forest. He’s not just asking her to marry him but also giving her a necklace that symbolizes their connection. This thoughtful gesture not only makes the proposal more meaningful but also shows that adding a personal touch can make the moment even more special. Consider including a symbolic item or a memory that holds significance for both of you.

Sony Pictures Animation The Princess Bride (1987)

Lesson: Be adventurous

In this beloved film, Westley (Cary Elwes) proposes to Buttercup (Robin Wright) by reciting the lines from their favorite book, “As you wish.” This creative and adventurous approach not only demonstrates his love for her but also shows that proposing in a unique way can be both memorable and heartwarming. If you’re looking for a way to make your proposal stand out, consider thinking outside the box and incorporating elements that reflect your shared passions or interests.

Universal Pictures The Sweetest Thing (2002)

Lesson: Be honest about your feelings

In this romantic comedy, Patrick (Thomas Jane) proposes to his girlfriend, Christine (Cameron Diaz), in a heartfelt and honest manner. He admits that he’s not perfect and that he’s not sure if he’ll ever be the right person for her, but he loves her and wants to try. This honesty not only shows vulnerability but also demonstrates that love isn’t about perfection—it’s about being open and genuine. If you’re unsure about how to express your feelings, this scene reminds us that honesty and transparency can be the most powerful aspects of any proposal.

Warner Bros. The Notebook (2004)

Lesson: Cherish the moment

Noah (Ryan Gosling) and Allie (Rachel McAdams) share a romantic proposal in The Notebook, surrounded by the very landscape that symbolizes their love story. This intimate and personal moment highlights the importance of creating a space where both of you can truly connect and cherish the proposal. Consider choosing a location that holds special meaning for both of you to make the moment even more meaningful.

Focus Features Pride & Prejudice (2005)

Lesson: Be patient

Mr. Darcy’s proposal in Pride & Prejudice is anything but impulsive. He takes the time to understand Elizabeth (Keira Knightley) and her values before asking her to marry him. This patience not only demonstrates his respect for her but also shows that taking the time to get to know each other can lead to a stronger foundation for your relationship. If you’re feeling rushed, this scene reminds us that patience and thoughtfulness are key components of a meaningful proposal.

Columbia Pictures When Harry Met Sally (1989)

Lesson: Communicate openly

In When Harry Met Sally, Harry and Sally (Billy Crystal and Meg Ryan) have a candid conversation about marriage, which eventually leads to a heartfelt moment where Harry admits his love for Sally. This open communication not only builds trust but also shows that expressing your feelings can be just as impactful as a traditional proposal. If you’re unsure about how to approach the topic, this scene emphasizes the importance of honesty and open dialogue in your relationship.

Warner Bros. The Proposal (2009)

Lesson: Be willing to take a chance

Margaret and Andrew’s relationship in The Proposal is built on a lie, but their proposal shows that sometimes, taking a chance on love can lead to something beautiful. This unconventional proposal reminds us that love isn’t always about perfection or following the rules—it’s about believing in the potential of a relationship and being willing to take that leap of faith. If you’re feeling unsure about the future, this scene encourages us to embrace the unknown and trust in the power of love.

20th Century Fox The Wedding Singer (1998)

Lesson: Embrace your unique style

Rob’s proposal in The Wedding Singer is chaotic and unconventional, but it’s also filled with passion and sincerity. This unapologetic approach shows that there’s no one-size-fits-all way to propose—what matters most is that the moment reflects your authentic self and your love for the person you’re asking to marry you. If you’re feeling constrained by societal expectations, this scene reminds us that being true to your own style can make for the most memorable proposal of all.

Sony Pictures Animation The Princess Bride (1987)

Lesson: Show your commitment

Westley’s proposal in The Princess Bride is not just about asking Buttercup to marry him—it’s about declaring his unwavering commitment to her. This unyielding dedication not only demonstrates his love but also sets the stage for a lifelong partnership built on trust and loyalty. If you’re unsure about how to convey your commitment, this scene underscores the importance of showing your partner that you’re fully invested in the relationship.

In the end, whether you’re inspired by the romance of Mr. Darcy’s words or the spontaneity of Rob’s airplane proposal, the key takeaway is that a successful proposal is one that truly reflects your love for your partner. Remember to prioritize communication, honesty, and creating a moment that feels uniquely special to both of you. And while pop culture may have set certain expectations, the most important thing is to make the proposal that feels right for you and your relationship. Good luck!