MomSkoop
Steve Carell shows up twice on this list, once as a newly separated dad and once as a tired suburban husband mistaken for a thief in New York. Directors Rob Reiner and Robert Zemeckis each claim two spots as well, so a few decades of crowd-pleasers are covered. I love that mix, because a date night pick has a tricky job. It has to win over two people with different moods, different snack rules, and different patience for slow scenes.
The picks ahead lean on sharp dialogue, big adventures, and love stories that don’t feel like homework. Some will make you laugh, and a couple might sneak up on you emotionally. Each one comes with a quick reason it works for two viewers, plus a few fun details to share during the opening credits. Which of you is grabbing the blanket, and who is in charge of the remote?
1. How to Lose a Guy in 10 Days
Two people walk into a relationship, and both of them are running a scam.
Andie Anderson writes a how-to column for Composure magazine, and her new assignment is to drive a man away in 10 days.
Ben Barry, an advertising executive, has his own secret.
He bet his boss he could make a woman fall for him within 10 days, and a big diamond account rides on the outcome.
Kate Hudson and Matthew McConaughey play these sneaky lovebirds with fast, silly energy.
Watching each of them refuse to quit, no matter how ridiculous things get, is half the fun.
The movie works for couples because it gives both viewers someone to root for.
One of you can cheer for Andie’s outrageous tactics while the other defends poor Ben through them.
Keep an eye out for the karaoke scene with Carly Simon’s “You’re So Vain,” which turns into a playful public battle.
Andie’s yellow gown at a later party also became one of the most talked-about outfits in the film.
Donald Petrie directed this 2003 romantic comedy, and it moves quickly at under two hours.
Afterward, you can compare notes on which move was the most annoying, and which one you would never try at home.
2. Hitch
Dating advice sounds smooth until the expert starts tripping over his own rules.
Will Smith plays Alex “Hitch” Hitchens, a New York “date doctor” who helps shy men win over the women they admire.
His newest client is Albert Brennaman, a lovable accountant played by Kevin James.
Albert has a crush on a wealthy celebrity, and his dance moves need serious repair.
Meanwhile, Hitch meets Sara Melas, a sharp gossip columnist played by Eva Mendes.
She is not easily charmed, and his polished tricks keep backfiring in very public ways.
The dance lesson between Hitch and Albert is a highlight for plenty of viewers.
Kevin James commits to his goofy moves so fully that you may find yourself copying them on the couch.
For date night, this film offers a nice balance of slapstick and sweet moments.
It also sparks easy conversation about first-date habits, which can be pretty funny if you share your own awkward stories.
Andy Tennant directed the movie, and it hit theaters in February 2005, just in time for Valentine’s Day.
Fair warning, though, there’s a scene involving a food allergy that might make you think twice before ordering shellfish.
3. Crazy, Stupid, Love
Steve Carell starts this movie in a rough spot, sitting in a car while his wife asks for a divorce.
His character, Cal Weaver, then lands at a bar where a smooth ladies’ man named Jacob Palmer decides to rebuild him.
Ryan Gosling plays Jacob, and the makeover scenes are a delight.
Watching Cal lose his sneakers and gain confidence gives the first half plenty of easy laughs.
Several love stories run side by side here.
Julianne Moore plays Cal’s wife Emily, while Emma Stone plays Hannah, a law student who isn’t impressed by Jacob’s usual lines.
One scene borrows the famous lift from Dirty Dancing, and it’s a sweet nod for anyone who knows the original.
Gosling and Stone later reunited for La La Land, so you can spot their early chemistry here.
The film also includes a twist that changes how several characters connect.
Try to avoid spoilers before watching, because the reveal lands best as a surprise.
Directed by Glenn Ficarra and John Requa, the movie came out in 2011.
It suits couples who like a mix of comedy and honest moments about marriage, crushes, and second chances.
4. 10 Things I Hate About You
Shakespeare probably never pictured his play involving a paintball date and a marching band.
Still, this 1999 teen comedy is a modern take on The Taming of the Shrew, set at Padua High School.
Bianca Stratford can’t date until her older sister Kat does, and Kat has zero interest in the boys at school.
So new student Cameron, played by Joseph Gordon-Levitt, arranges for mysterious Patrick Verona to win Kat over.
Julia Stiles gives Kat a sharp tongue and a strong point of view.
Heath Ledger plays Patrick with a sly grin that makes his slow change fun to watch.
The most famous moment comes when Patrick sings “Can’t Take My Eyes Off You” in the bleachers.
It’s a goofy, bold gesture, and security chasing him around the stadium makes it even better.
Fun fact: the school scenes were filmed at Stadium High School in Tacoma, Washington.
The building looks like a castle, which fits the Shakespeare connection nicely.
Gil Junger directed this one, and it runs about an hour and a half.
Kat’s poem near the end might get you both a little misty, so keep the tissues close by.
5. When Harry Met Sally…
Can men and women just be friends?
Harry Burns says no during a long car ride from Chicago to New York, and Sally Albright strongly disagrees.
That argument kicks off a story that spans years of run-ins, friendships, and other relationships.
Billy Crystal and Meg Ryan trade quick lines that still sound fresh today.
Nora Ephron wrote the screenplay, and Rob Reiner directed the film in 1989.
Their conversations about dating, breakups, and holiday parties feel like chats you might actually overhear.
The scene at Katz’s Delicatessen in New York is the one people quote most.
The line “I’ll have what she’s having” is spoken by a customer played by Estelle Reiner, the director’s mother.
Between scenes, the film cuts to older couples telling how they met.
These short interviews add sweet little breaks and might inspire you to share your own story.
Autumn in New York looks gorgeous here, with fallen leaves and city walks.
It makes a great pick on a crisp fall evening, though the New Year’s Eve scenes also make it a fun choice in late December.
6. The Princess Bride
A grandfather visits his sick grandson with a storybook, and the boy is not excited at first.
He worries it might be a kissing book, which gives the movie one of its best running jokes.
Peter Falk plays the grandfather, and Fred Savage plays the doubtful kid.
Their story frames the main tale of Westley, a farm boy, and Buttercup, the woman he loves.
Cary Elwes and Robin Wright lead the adventure, which includes pirates, giants, and a swamp full of large rodents.
Mandy Patinkin steals plenty of scenes as Inigo Montoya, a swordsman with a very famous introduction.
William Goldman wrote the novel and the screenplay, so the humor stays sharp from start to finish.
Rob Reiner directed it, and it hit theaters in 1987.
This film may be the easiest win on the list for couples with different tastes.
One person gets sword fights and wisecracks, while the other gets true love and a fairy tale.
André the Giant plays Fezzik, a gentle strongman who loves rhyming.
Expect to repeat lines like “As you wish” and “Inconceivable!” for days after the credits roll.
7. Back to the Future
Eighty-eight miles per hour is the magic number in this one.
Hit that speed in Doc Brown’s DeLorean, and you might end up decades in the past.
That’s what happens to Marty McFly, played by Michael J.
Fox.
He lands in 1955, accidentally gets in the way of his parents meeting, and has to fix it fast.
Christopher Lloyd plays Doc Brown with wild hair and wide eyes.
His panicked shouts about 1.21 gigawatts are a highlight, even if you don’t understand the science.
Here’s a fun bit of history: Eric Stoltz was first cast as Marty, and he filmed scenes before the role went to Fox.
It’s hard to picture anyone else in that red vest now.
For date night, this pick blends action, comedy, and a bit of romance at a school dance called Enchantment Under the Sea.
It also gives you both something to talk about, like where you’d go if you could travel in time.
Robert Zemeckis directed the film, which came out in July 1985.
If you love it, two sequels are ready for future date nights.
8. The Wedding Singer
Big hair, shiny jackets, and synth-pop songs fill this love letter to the 1980s.
The story is set in 1985, and the costumes alone deserve a pause button.
Adam Sandler plays Robbie Hart, a singer who performs at other people’s weddings.
After his own fiancée leaves him at the altar, he becomes the gloomiest entertainer in town.
Drew Barrymore plays Julia Sullivan, a kind waitress who works the same receptions.
She’s engaged to someone else, which makes their growing friendship complicated.
Sandler and Barrymore have an easy, sweet chemistry that later brought them together again in 50 First Dates and Blended.
Here, their scenes feel gentle and funny instead of loud.
The soundtrack is packed with hits from the era, and the movie includes a cameo from Billy Idol himself.
Robbie also sings an original tune called “Grow Old with You,” which is short, simple, and lovely.
Frank Coraci directed the film, released in February 1998.
It’s a solid pick if one of you loves Sandler comedies and the other prefers a softer love story, since this one delivers both.
9. Date Night
Watching a movie called Date Night on date night feels a little like a wink, and that’s part of the charm.
Steve Carell and Tina Fey play Phil and Claire Foster, a busy New Jersey couple stuck in a routine.
To shake things up, they head to a fancy Manhattan restaurant without a reservation.
They grab a table under another couple’s name, which turns out to be a terrible idea.
Soon, the Fosters are being chased by people who think they are thieves.
The night spirals into car chases, wrong turns, and a lot of nervous bickering.
Carell and Fey are both comedy veterans, and their improvised-feeling banter keeps things moving.
Mark Wahlberg also appears as a security expert who never seems to own a shirt.
Shawn Levy directed the film, which opened in April 2010.
It runs about 88 minutes, making it a smart choice when you both want laughs without a late bedtime.
The movie also has a sweet core about long-term couples who still like each other.
After watching, you might feel grateful that your own evening involves popcorn instead of a getaway car.
10. The Secret Life of Walter Mitty
Daydreamers, this one is for you.
Walter Mitty spends his days zoning out into wild fantasies while working in the photo department at Life magazine.
Ben Stiller directed the film and stars as Walter.
When a key negative for the magazine’s final print issue goes missing, he has to track down a famous photographer to find it.
That photographer, Sean O’Connell, is played by Sean Penn.
The hunt sends Walter to places like Greenland and Iceland, and the scenery is stunning.
One standout scene shows Walter skateboarding down a long mountain road.
It’s quiet, freeing, and a nice moment to simply soak in with your partner.
Kristen Wiig plays Cheryl, a coworker Walter likes but struggles to talk to.
Their sweet, low-key romance adds a gentle thread to the bigger adventure.
The story is loosely based on a 1939 short story by James Thurber.
Released on Christmas Day 2013, the film works well for couples who like travel, music, and a bit of inspiration, and it might even get you planning your next trip together.
11. You’ve Got Mail
Long before texting, there was the cheerful voice announcing new email.
Kathleen Kelly and Joe Fox trade messages online without knowing each other’s real names.
In real life, they are business rivals.
Kathleen runs a small children’s bookstore called The Shop Around the Corner, while Joe’s giant Fox Books store opens nearby.
Meg Ryan and Tom Hanks play the pair, marking their third movie together after Joe Versus the Volcano and Sleepless in Seattle.
Their chemistry is easy and familiar by this point.
Nora Ephron directed and co-wrote the 1998 film.
It’s a remake of the 1940 movie The Shop Around the Corner, which told a similar story with letters instead of email.
The Upper West Side of Manhattan looks lovely here, with flower shops, cafes, and fall leaves.
You may want to grab a fancy coffee and a new book after watching.
For couples, the fun lies in watching two smart people argue while slowly falling for each other.
It also leads to a fun talk about how dating has changed, from dial-up internet to modern apps.
12. Mr. & Mrs. Smith
Every marriage has secrets, but John and Jane Smith take things way too far.
Both are highly trained hired operatives working for rival agencies, and neither knows the truth about the other.
Brad Pitt and Angelina Jolie play the couple, who met in Bogotá and married quickly.
Years later, their suburban life feels dull, and their talks with a marriage counselor are hilariously stiff.
Things change fast when they are both assigned to the same target.
Suddenly, each spouse discovers the other’s double life, and the house becomes a battlefield.
Doug Liman directed the film, which came out in June 2005.
The action scenes are big and flashy, but the jokes about married life give the story its spark.
This pick suits couples where one person craves explosions and the other wants romance.
The film delivers both, plus some sharp banter during the chaos.
A dinner scene where the two try to outsmart each other is a fun standout.
Just maybe skip it if you’re in the middle of a real argument about whose turn it is to do the dishes.
13. Silver Linings Playbook
A dance competition might be the last thing you’d expect in a story about football fans and family drama.
Yet that’s exactly where this offbeat romance takes you.
Bradley Cooper plays Pat Solitano, a man with bipolar disorder who returns home to Philadelphia after a stay in a psychiatric hospital.
He is set on winning back his estranged wife.
Then he meets Tiffany, a blunt young widow played by Jennifer Lawrence.
She offers to help Pat, but only if he agrees to be her partner in a dance contest.
Lawrence won the Academy Award for Best Actress for this role.
Robert De Niro also appears as Pat’s father, a devoted Eagles fan with strong superstitions.
David O.
Russell wrote and directed the film, which is based on a novel by Matthew Quick.
It premiered in 2012 and mixes humor with serious moments about mental health and grief.
Because of its themes and strong language, it fits nights when you both want something with more depth.
The chaotic family scenes are funny, and the final dance gives you plenty to cheer for.
14. About Time
On his 21st birthday, Tim Lake gets surprising news from his dad.
The men in their family can travel back in time to moments from their own lives.
Domhnall Gleeson plays Tim, who decides to use this gift to find love.
He meets Mary, played by Rachel McAdams, and keeps redoing awkward moments to get things right.
Bill Nighy plays Tim’s dad with a dry, lovable humor.
Their father-son scenes, including ping-pong games and beach walks, are some of the most touching in the film.
Richard Curtis wrote and directed the movie, which came out in 2013.
He also wrote Notting Hill and Love Actually, so you can expect British charm and witty dialogue.
Much of the film takes place in London and Cornwall, and the seaside scenery looks beautiful.
A rainy wedding scene is chaotic, funny, and sweet all at once.
Fair warning, this one leans more emotional in its second half.
It’s a great choice if you both enjoy a story that makes you laugh and then quietly reminds you to appreciate ordinary days together.
15. Forrest Gump
A box of chocolates and a bus stop bench set the stage for this one.
Forrest Gump, a kind-hearted man from Alabama, tells his life story to strangers waiting nearby.
Tom Hanks plays Forrest, and his journey crosses paths with major moments in American history.
He runs across the country, plays ping-pong, and meets several U.S. presidents along the way.
Through it all, Forrest stays devoted to Jenny, his childhood friend played by Robin Wright.
Their on-and-off connection is the heart of the movie.
Robert Zemeckis directed the film, which came out in 1994 and won six Academy Awards.
Those wins included Best Picture and Best Actor for Hanks.
The story is based on a novel by Winston Groom.
Gary Sinise also stands out as Lieutenant Dan, Forrest’s commanding officer in the Vietnam War.
At about two hours and 22 minutes, it’s the longest pick here, so start early.
It works best when you both want a big, moving story with plenty of humor, and you’ll likely be quoting “Run, Forrest, run!” at each other the next morning.