Movies Like The Proposal

In The Proposal, audiences are treated to a delightful mix of humor, romance, and unexpected turns as two people embark on a journey that takes them from mere acquaintances to something much more. If you’re enchanted by the story of a demanding boss and her assistant finding love in the most unexpected circumstances and are craving similar tales of laughter, love, and life’s little surprises, here’s a curated list of 15 movies like The Proposal that share the same spirit and charm. Hope you can discover your favorite movies like The Proposal with us!

  1. Crazy, Stupid, Love.
  2. 27 Dresses
  3. The Holiday
  4. Bridesmaids
  5. Silver Linings Playbook
  6. Leap Year
  7. Just Go With It
  8. The Ugly Truth
  9. Friends with Benefits
  10. It’s Complicated
  11. Bridget Jones’s Diary
  12. Crazy Rich Asians
  13. No Strings Attached
  14. How to Lose a Guy in 10 Days
  15. The Big Sick

Crazy, Stupid, Love. (2011) – Streaming on TNT, TBS

This film is a clever and heartfelt story about the complexities of love seen through the interconnected lives of several individuals. At the center is a middle-aged man whose life is upended when he discovers his wife’s infidelity. As he ventures back into the dating world with the help of a suave, younger friend, the movie weaves through various aspects of love and relationships, making it a humorous yet poignant exploration of the human heart.

27 Dresses (2008) – Streaming on Hulu, Fubo TV

A romantic comedy about the eternal bridesmaid, Jane, who has been in 27 weddings. Her world turns upside down when her sister gets engaged to the man Jane secretly loves. As she prepares for yet another bridesmaid duty, she encounters a cynical journalist who sees her story as his next big piece. This film beautifully combines humor with moments of introspection, exploring themes of love, sacrifice, and the courage to stand up for your own happiness.

The Holiday (2006) – Streaming on DIRECTV, Fubo TV

This film follows two women, Iris and Amanda, from different countries, who agree to a home exchange to escape heartbreak during the holiday season. In their new environments, they each encounter unexpected romances that help them rediscover the joy of life. The film is a feel-good story about healing and new beginnings.

Bridesmaids (2011) – Streaming on Peacock Premium

This comedy takes a look at the competitive and often chaotic nature of being a bridesmaid. When Annie is asked to be the maid of honor for her best friend Lillian, she faces the wild antics of the bridal party and her own life’s unraveling. The movie is a hilarious yet touching look at friendship, love, and the personal growth that often comes with navigating the rocky road to a friend’s wedding. Don’t miss this film if you are looking for more movies like The Proposal.

Silver Linings Playbook (2012) – Streaming on DIRECTV, Netflix

A blend of drama, comedy, and romance, this film follows Pat and Tiffany, two individuals with complex emotional backgrounds who come together to form an unexpected bond. As they practice for a dance competition, their relationship helps them to confront their issues and rediscover the silver linings in their lives. The movie is a touching portrayal of mental health, healing, and the unexpected ways love can heal and transform us.

Leap Year (2010) – Streaming on DIRECTV

This charming film tells the story of Anna, who plans to propose to her boyfriend on Leap Day—an Irish tradition—only to find herself on a detour through the Irish countryside with Declan, a handsome but surly innkeeper. As they journey together, Anna begins to question her feelings and what she truly wants in life. It’s a story filled with beautiful landscapes, cultural charm, and a heartwarming look at love and destiny.

Just Go With It (2011) – Streaming on Peacock Premium, Fubo TV

In this comedy, a plastic surgeon convinces his loyal assistant to pose as his soon-to-be ex-wife to cover up a lie he told his much younger girlfriend. As they take a trip to Hawaii with their ‘children,’ the lines between truth and deception blur. The film is a humorous and sometimes heartfelt look at love, lies, and the unexpected relationships that can form when we pretend to be someone we’re not.

The Ugly Truth (2009) – Streaming on DIRECTV

A battle of the sexes ensues when a romantically challenged morning show producer is teamed up with her chauvinistic correspondent. He promises to help her find love using his ‘rules’ of attraction, leading to a series of hilarious and enlightening encounters. The film is a witty, sometimes crude exploration of love, attraction, and the stereotypes we navigate in the quest for romance.

Friends with Benefits (2011) – Streaming on Netflix

This film explores the complexities of adding sex to a friendship as two friends agree to start a no-strings-attached relationship. As they navigate this new arrangement, they start to realize that separating emotions from physical intimacy is more complicated than they thought. The movie is a witty and insightful look at modern relationships, friendship, and the blurred lines between love and lust. It is also one of the movies like The Proposal on Netflix.

It’s Complicated (2009) – Streaming on DIRECTV, Amazon Prime Video

A romantic comedy about Jane, a divorced woman who starts an affair with her ex-husband, Jake, who’s married to a younger woman. At the same time, she’s drawn to Adam, her architect, who’s recovering from his own divorce. As Jane navigates these complicated relationships, she learns more about her desires and herself. The film is a humorous and honest look at love, relationships, and the often complicated journey to finding happiness.

Bridget Jones’s Diary (2001) – Streaming on Fubo TV

Let’s dive into the following excellent rom com movies like The Proposal. This film is a witty and endearing adaptation of Helen Fielding’s novel, following the life of Bridget Jones, a single woman who’s determined to improve herself while she looks for love. Bridget’s hilarious and often poignant diary entries reveal her adventures and misadventures in the world of dating, work, and family. It’s a relatable, humorous look at the life of a modern woman navigating the ups and downs of love and life.

Crazy Rich Asians (2018) – Streaming on DIRECTV, Hulu

When New Yorker Rachel Chu accompanies her longtime boyfriend, Nick Young, to his best friend’s wedding in Singapore, she’s unprepared to learn that Nick’s family is extremely wealthy and he’s considered one of the country’s most eligible bachelors. The film is a lavish, heartwarming, and humorous tale of love, family, and the clash of cultural norms.

No Strings Attached (2011) – Streaming on Paramount+

This movie looks at the complicated relationship between two friends who decide to make their relationship physical without emotional attachment. As they try to maintain their friendship while satisfying their physical needs, they discover that they want more. It’s a humorous and touching examination of friendship, love, and the modern dilemma of romantic relationships.

How to Lose a Guy in 10 Days (2003) – Streaming on Paramount+

In this romantic comedy, a magazine writer embarks on a mission to start and end a relationship in 10 days to write an article for her work, while her unsuspecting target, an advertising executive, bets he can make any woman fall in love with him in the same timeframe. As their deceptive plots unfold, they find themselves genuinely falling for each other, leading to comedic and heartwarming moments.

The Big Sick (2017) – Streaming on Amazon Prime Video

Based on the real-life love story of Kumail Nanjiani and Emily V. Gordon, this film tells the story of Pakistan-born aspiring comedian Kumail, who connects with grad student Emily after one of his standup sets.

Each of these films, like The Proposal, offers a unique blend of humor, romance, and life’s unexpected twists. They capture the essence of finding love and laughter in the most unexpected places, making them perfect for anyone looking to dive into heartwarming and humorous stories of love and life. Discuss more with other movie lovers on movies like The Proposal Reddit!