“Sure,” they texted, “a movie sounds great”. Between skipping down the street and keeping the butterflies at bay, you’ve given no thought to what movie you’ll be watching. After a half-hour browse and a courteous “I don’t mind, you pick” you chooseThe Hangover, a safe bet. But this special night has no spark. There’s nothing to talk about, and they’re checking their phone constantly, probably to see what time it is.
Don’t let this happen to you. Movies and dates go together like butter and popcorn because cinema is among the most wonderful shared experiences: stories, laughter, and emotion help blossoming connections bloom.So whether you’re dating the one or just having fun, be ready with good date night movies that wow. The best among these will make lasting impressions that show you have great taste in films, increasing the chances of a second date.
30. ‘Wedding Crashers’ (2005)
Directed by David Dobkin
Owen WilsonandVince Vaughnstar as best friends, John and Jerry, who, every wedding season, attend strangers' weddings where they become the life of the party. When they crash the Secretary of Treasury’s (Christopher Walken) daughter’s wedding, they find themselves a bit in over their heads after Jerry hooks up with the Secretary’s other daughter (Ilsa Fisher) and when John is immediately taken by another daughter (Rachel McAdams), leading the duo on an unexpected stay with the family at their vacation home.
Wedding Crashersis a hilarious romantic comedy that, despite its plot, also has sentimental moments that make it the ideal date night flick. The movie is full of physical and slapstick comedy that effectively breaks the ice on those slightly awkward first dates, providing enough comic relief to put any couple at ease. Between the string of ridiculous chaos that ensures and the all-star cast,Wedding Crashersis guaranteed to leave a lasting impression (in a good way!)
Wedding Crashers
29. ‘The Princess Bride’ (1987)
Directed by Rob Reiner
When a boy (Fred Savage) is home sick from school, his grandfather (Peter Falk) tells him a story about a brave farmboy, Westley (Cary Elwes), who must find his true love, Princess Buttercup (Robin Wright), before she marries a loathsome prince (Chris Sarandon). With the help of a few friends, Westley must overcome a series of obstacles and fight his way to rescue his beloved princess before it’s too late.
The Princess Brideisa 1980s cult classicthat puts a humorous spin on a classic fairy tale, conveying the perfect balance of comedic romance and thrilling action to satisfy any viewer. The movie ranks as a crucial date night movie because it has something for everyone, so if you’re at odds with your date about what to watch,The Princess Brideis the best choice to settle any debate.
The Princess Bride
28. ‘Crazy, Stupid, Love.’ (2011)
Directed by Glenn Ficarra and John Requa
Steve Carellstars as a husband and family man, Cal Weaver, who, despite his seemingly picturesque life, discovers that his wife has been having an affair and wants a divorce. At the age of forty, Cal finds himself completely lost in the modern dating world and decides to hire a smooth-talking player, Jacob Palmer (Ryan Gosling), to teach him the ropes.
Crazy, Stupid, Loveis an excellent pick for any date night and will have viewers both laughing and crying by the end. Gosling and Carell are a hysterical duo who pull out all the stops with their deadpan and sarcastic humor, presenting a difficult situation in a relatable and approachable light. Whether you’re in your 20s or in your 40s,Crazy, Stupid, Loveis noted for its realistic view of anyone who finds themselves struggling in the dating world, deeming it to be a solid pick for date night.
Crazy, Stupid, Love
27. ‘The Wedding Singer’ (1998)
Directed by Frank Coraci
Adam Sandler stars as a wedding singer, Robbie Hart, who is a bit of a local celebrity and comes highly recommended by every couple who hires him. When Robbie is engaged to be married to his longtime sweetheart, he completely falls apart after she leaves him at the altar. Despite swearing off performing at weddings, Robbie agrees to help a soon-to-be bride, Julia (Drew Barrymore), plan her upcoming wedding, but as they spend more time together, Julia begins to have second thoughts.
Set in 1985,The Wedding Singeris ranked as the ultimate romantic comedy and was the first collaboration between Sandler and Barrymore, who have an undeniable on-screen chemistry that is impossible to resist.Sandler and Barrymore deliver lighthearted humor and natural romance that setsThe Wedding Singerapart from other rom-coms. For those looking for an easy-going love story full of laugh-out-loud comedy,The Wedding Singeris right up your alley for your next date night.
The Wedding Singer
26. ‘Forgetting Sarah Marshall’ (2008)
Directed by Nicholas Stoller
When Peter Bretter (Jason Segel) finds out that his longtime girlfriend and television star, Sarah Marshall (Kristen Bell), is leaving him, he falls into a deep depression and is convinced by his brother to take a vacation to Hawaii. While this is great advice, Peter’s trip takes an unexpected turn when Sarah and her new boyfriend (Russell Brand) are staying at the same resort. Despite the awkward coincidence, Peter ends up spending time with one of the hotel’s employees (Mila Kunis) who breaks him out of his shell and reminds him that life goes on.
Forgetting Sarah Marshallis a raunchy romantic comedy that pulls out all the stops of the unfortunate and wonderfulaspects of love and heartbreak, woven intricately through non-stop humor. Segel and Kunis are a pure delight who play well off each other’s witty, dry humor, creating a more than convincing on-screen couple. Aside from Segel and Kunis, the supporting cast is another underrated gem in this outrageous comedy and will have everyone in stitches by the end of the date.
Forgetting Sarah Marshall
25. ‘An Affair to Remember’ (1957)
Directed by Leo McCarey
Perhaps one of the most timeless romantic movies isAn Affair to Remember, which pairs beloved actorCary GrantandBritish thespian Deborah Kerr. In the movie, strangers Nickie Ferrante and Terry McKay spark a connection aboard an ocean liner in transit across the Atlantic ocean. Despite being betrothed to other people, Nickie and Terry promise to see each other on top of the Empire State Building if they’re sure of each other after six months.
However, an unfortunate accident prevents Terry from fulfilling his promise.It’s an essential romance film to watch due in large to the palpable chemistry between its lead characters, as well as its plot that highlights how love truly conquers all odds. Watching the film with your date can easily turn into a core memory, with you and your partner getting lost in the movie’s dramatic shipboard romance story.– Jom Elauria
An Affair to Remember
24. ‘Palm Springs’ (2020)
Directed by Max Barbakow
A chance encounter at a Palm Springs wedding becomes a life-altering event for wedding attendees Nyles (Andy Samberg) and Sarah (Cristin Milioti). Thrust into a time loop, they find themselves reliving the same day over and over. What begins as surreal panic becomes a catalyst for personal growth. As they navigate this bizarre predicament, they confront past mistakes, shed their inhibitions, and discover a surprising connection.
You can spice up your date night withPalm Springsas it offers a thought-provoking and hilarious plot. It takes the classic time-loop concept and injects it with humor and heart, with standout performances from Samberg and Milioti, making viewers laugh out loud while rooting for their unconventional love story. Beyond the entertainment,Palm Springsoffers plenty to discuss on your date.The unique blend of sci-fi and romance creates a conversation starter, which is perfect for getting to know your date’s perspective on love and destiny.– Jom Elauria
Palm Springs
23. ‘Bridesmaids’ (2011)
Directed by Paul Feig
One ofPaul Feig’s stronger comedies,Bridesmaidsis the go-to choice for anyone looking for a well-written flick that’s neither crass nor cheesy. Down-on-her-luck Annie (Kristen Wiig) has just been appointed maid of honor by her childhood best friend Lillian (Maya Rudolph). Although she’s elated about the engagement, deep down she’s scared about what this might mean for their friendship. Determined to give Lillian the best bridal experience, Annie pulls out all the stops to give the future bride what she wants.
But when Lillian’s other bridesmaids (Rose Byrne,Melissa McCarthy,Wendi McLendon-Covey, andEllie Kemper) start one-upping Annie, she starts bringing out her competitive side - even if it costs her her dignity. With memorable scenes like the food poisoning fiasco and Annie’s drunken airplane meltdown,Bridesmaidsdoesn’t shy awayfrom getting into Annie’s insecurities and victim complex, giving the comedy a much more genuine touch. —Dyah Ayu Larasati
Bridesmaids
22. ‘Nick and Norah’s Infinite Playlist’ (2008)
Directed by Peter Sollett
Nick and Norah’sInfinite Playlistromanticizesthe concept of date night: galavanting through New York City after hours, hopping from one bar to another, and falling in love with a stranger. Indie band bassist Nick (Michael Cera) is recently dumped by his hot ex-girlfriend Tris (Alexis Dziena). In an attempt to patch up his broken heart, Nick’s friends get him to perform a gig in the city to take his mind off Tris. There he meets Norah (Kat Dennings), who asks her to be her pretend boyfriend for five minutes, sealed with a fake kiss.
Their charade isn’t over yet. When Norah’s drunken best friend suddenly disappears, the two scour the streets looking for her, all while searching for an elusive secret show that’s been the talk of town. From sloppy make-out sessions to a man dressed up as a cig-smoking Jesus,Nick and Norah’s Infinite Playlistis the right choice to vicariously live through someone else’s date night. —Dyah Ayu Larasati
Nick and Norah’s Infinite Playlist
21. ‘The Holiday’ (2006)
Directed by Nancy Meyers
Whether it’s summer or winter, any time’s a good time for a cute Christmastime flick.The Holidayfollows two lovelorn women from two different continents. Amanda Woods (Cameron Diaz), an uber-successful movie trailer producer based in sunny Los Angeles, just got dumped by her cheating ex-boyfriend Ethan. Meanwhile, all the way in London, hapless wedding column writer Iris Simpkins (Kate Winslet) is still hung up over her unrequited love for her newly engaged colleague.
Following their chance encounter through a house exchange website, the two women impulsively decide to switch homes for the holidays. Little do they know, they’re about to meet their potential loves during their silly little trip.Pairing Diaz’s cool-girl goofinessand Winslet’s introverted charm,The Holidayis a safe bet for anyone looking for a lighthearted moviewith genuine chemistry and an abundance of chuckles. —Dyah Ayu Larasati
