19 Hilarious Movies About First Dates Gone Wrong

1. 50 First Dates 2004，IMDB Rating: 6.8, IMDB Votes: 386137, ID: 0343660
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In ’50 First Dates’, the charming chemistry between Adam Sandler and Drew Barrymore is undeniable. However, the plot where a woman is made to pay for everything on a date resonates differently after our topic. It makes one appreciate the character of Henry (Sandler) who, despite Lucy’s (Barrymore) memory loss, strives every day to win her heart anew.
2. 10 Things I Hate About You 1999，IMDB Rating: 7.3, IMDB Votes: 392591, ID: 0147800
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The movie ’10 Things I Hate About You’ presents a unique take on dating and relationships. The scenario of a woman paying for a date is humorously reversed when Patrick (Heath Ledger) is paid to date Kat (Julia Stiles). This twist adds a layer of irony to our topic, making the movie even more enjoyable.
3. Forgetting Sarah Marshall 2008，IMDB Rating: 7.1, IMDB Votes: 304357, ID: 0800039
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In ‘Forgetting Sarah Marshall’, the protagonist’s journey to self-discovery after a painful breakup offers a refreshing perspective on relationships. The topic of a woman paying on a date underscores the importance of honesty and respect in any relationship, elements that are beautifully explored in this film.
4. When Harry Met Sally… 1989，IMDB Rating: 7.7, IMDB Votes: 245116, ID: 0098635
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The classic ‘When Harry Met Sally…’ explores the complexities of male-female friendships and romantic relationships. In light of our topic, it underscores the importance of mutual respect and understanding in dating, making it a timeless watch.
5. Notting Hill 1999，IMDB Rating: 7.2, IMDB Votes: 346543, ID: 0125439
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The film ‘Notting Hill’ beautifully portrays the love story between a famous actress and a humble bookstore owner. In the context of our topic, it emphasizes the value of sincerity and equality in a relationship, making it a delightful and thought-provoking watch.
6. Serendipity 2001，IMDB Rating: 6.8, IMDB Votes: 122181, ID: 0240890
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Serendipity is a romantic comedy that revolves around the concept of fate and destiny. The movie’s plot, where the protagonists leave their relationship up to fate, could be seen as a metaphor for the unpredictability of dating. However, the male lead’s actions are far from the deceitful behavior in the user’s topic. The movie is light-hearted and charming, but some may find the plot’s reliance on coincidences a bit too much.
7. Roman Holiday 1953，IMDB Rating: 8.0, IMDB Votes: 148813, ID: 0046250
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Roman Holiday is a classic romantic comedy that tells the story of a princess who escapes her royal duties for a day of freedom in Rome. The male lead, a reporter, discovers her identity and sees an opportunity for an exclusive story. However, he doesn’t deceive her for personal gain, unlike the scenario in the user’s topic. The movie is praised for its performances and is considered a classic in the genre.
8. Pitch Perfect 2012，IMDB Rating: 7.1, IMDB Votes: 333279, ID: 1981677
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Pitch Perfect is a musical comedy that focuses on the competitive world of a cappella singing. The movie features strong female characters who navigate their personal and professional lives. However, the plot doesn’t directly relate to the user’s topic of deceptive dating experiences. Despite some clichéd elements, the movie is praised for its performances and musical numbers.
9. Autumn in New York 2000，IMDB Rating: 5.6, IMDB Votes: 28476, ID: 0174480
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Autumn in New York is a romantic drama that tells the story of a middle-aged playboy who falls for a much younger woman. The male lead’s initial insincerity might resonate with the user’s topic, but the movie’s focus is more on the bittersweet aspects of love. The film has been criticized for its clichéd plot and lack of chemistry between the leads.
10. Pride & Prejudice 2005，IMDB Rating: 7.8, IMDB Votes: 335267, ID: 0414387
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Pride & Prejudice is a timeless romance that explores the themes of pride, prejudice, and misunderstandings in relationships. While the male lead, Mr. Darcy, initially comes off as proud and aloof, his character is far from the deceitful date in the user’s topic. The movie is praised for its faithful adaptation of Jane Austen’s novel and the performances of its leads.
11. Stardust 2007，IMDB Rating: 7.6, IMDB Votes: 286744, ID: 0486655
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As a software engineer who loves coding and gaming, I found ‘Stardust’ to be a delightful escape from reality. The movie’s fantasy elements, combined with the romantic storyline, provided a perfect balance of excitement and emotion. The plot twist where the protagonist, Tristan, turns out to be the rightful king of Stormhold was unexpected and added an extra layer of intrigue. However, the character of Captain Shakespeare felt somewhat out of place and disrupted the flow of the story. Overall, ‘Stardust’ is a charming movie that offers a magical journey filled with adventure and romance.
12. Her 2013，IMDB Rating: 8.0, IMDB Votes: 677634, ID: 1798709
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The movie ‘Her’ resonated with me as a tech enthusiast. It explores the complex relationship between humans and artificial intelligence, presenting a future where love transcends physical boundaries. The performances by Joaquin Phoenix and Scarlett Johansson were sincere and moving, making the unconventional love story believable. However, the film also served as a cautionary tale about our increasing reliance on technology, which I found thought-provoking. ‘Her’ is a beautifully crafted film that combines romance, science fiction, and social commentary in a unique and engaging way.
13. The Princess Bride 1987，IMDB Rating: 8.0, IMDB Votes: 454418, ID: 0093779
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As someone who enjoys comedy and romance, ‘The Princess Bride’ was a delightful watch. The film’s blend of humor, adventure, and romance was refreshing. The characters were charming and the dialogue was witty, making the film enjoyable from start to finish. However, the film’s parody of classic fairy tales might not appeal to everyone. Despite this, ‘The Princess Bride’ remains a timeless classic that offers a unique and entertaining take on the traditional fairy tale genre.
14. Bridget Jones’s Diary 2001，IMDB Rating: 6.8, IMDB Votes: 266093, ID: 0243155
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Bridget Jones’s Diary is a charming and funny movie about a woman navigating her love life with humor and honesty. In the context of a first date, Bridget’s resilience and optimism in the face of disappointment could serve as an inspiration. Despite the awkwardness of the situation, the movie encourages viewers to find humor in life’s imperfections and to keep an open mind when things don’t go as expected.
15. The Fault in Our Stars 2014，IMDB Rating: 7.7, IMDB Votes: 404540, ID: 2582846
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The Fault in Our Stars is a poignant film about two young people who fall in love while dealing with serious health issues. In the context of a first date, the movie underscores the importance of authenticity and kindness. It reminds viewers that genuine connections are built on honesty and understanding, not on pretenses or manipulative tactics.
16. Me Before You 2016，IMDB Rating: 7.4, IMDB Votes: 292218, ID: 2674426
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Me Before You is a touching film about finding love in unexpected places and learning to live life to the fullest. In the context of a first date, the movie highlights the importance of sincerity and respect in building a relationship. It suggests that a memorable date doesn’t necessarily have to be extravagant, but it should be genuine and considerate.
17. The Vow 2012，IMDB Rating: 6.8, IMDB Votes: 206187, ID: 1606389
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The Vow is a romantic drama about a soldier who falls for a conservative college student while he’s home on leave. The movie doesn’t provide much context about their first date, but it’s clear that the male lead is committed to winning her heart again after she suffers severe memory loss. The topic of the guy forgetting his wallet and making the girl pay doesn’t align with the storyline, as the movie emphasizes on love, commitment, and the lengths one would go to keep a promise.
18. The Longest Ride 2015，IMDB Rating: 7.0, IMDB Votes: 89650, ID: 2726560
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The Longest Ride centers on the star-crossed love affair between Luke, a former champion bull rider, and Sophia, a college student. Their first date is quite memorable as they help rescue an elderly man from a car crash. The topic of the guy forgetting his wallet and making the girl pay on the first date doesn’t align with the storyline, as the movie showcases a gentlemanly behavior from Luke and emphasizes on enduring love across time and circumstances.
19. The Best of Me 2014，IMDB Rating: 6.7, IMDB Votes: 77943, ID: 1972779
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‘The Best of Me’ revolves around high-school sweethearts reunited after 20 years. The movie explores the theme of second chances in love, which could resonate with someone who has experienced a disappointing first date. However, the film’s lack of depth and reliance on clichés might mirror the superficiality of the man’s excuse about forgetting his wallet on the date.