7 romance movies for your perfect date night

By Gen Terblanche30 May 2023

7 romance movies for your perfect date night

Snuggle up, lovers. Whether you’re coupled up or just dreaming of The One, we’ve put together the ultimate classic romcom playlist to fill your nights with charm and laughter. We have all your favourite things – peasants and princesses, kissing in the rain, mutual pining, ridiculous best friends, Hollywood’s dream jobs, inspiring weird dates, and people who genuinely like each other. We’re talking quippy. We’re talking quotable. We’re talking good vibes only!

13 Going On 30

13 going on 30 is on Showmax

This 2004 film features the ultimate second chance romance. On nerdy Jenna Rink’s (Christa B Allen) 13th birthday she gets backstabbed by some popular mean girls, and makes a wish to be “30, flirty, and thriving”. Her wish is granted when the “magic wishing dust” on the doll house, made by her best friend Matty (Sean Marquette), sprinkles down on her, and she wakes up with her 13-year-old consciousness in her 30-year-old body and life.

Grownup Jenna (Jennifer Garner at her most charming) seems to have it all – a luxe New York apartment, a job as a fashion magazine editor, a hot bod and a boyfriend. There’s a big problem, though. Grownup Matty (played by Mark Ruffalo), now a romantic, struggling photographer, reveals that Jenna became successful by becoming a mean girl herself – and that her grownup BFF is now Lucy (Judy Greer), the mean girl ringleader. Jenna races to set things right before it’s too late and Matty marries someone else.

The best bits: The joy, kindness and silliness Jenna brings to everyday life as she sees the grownup world through young eyes – and how a lot of adult cruelty just flies right over her head. Her authenticity convinces a room full of hardened publication industry pros to get onboard with her new vision for the magazine during her big presentation. And there’s a killer choreographed group dance scene to Michael Jackson’s Thriller. Cynicism begone.

Notable quotable: “All of us want to feel something that we’ve forgotten or turned our backs on because maybe we didn’t realise how much we were leaving behind.” – Jenna Rink

50 First Dates

50 First Dates is on Showmax

This 2004 Adam Sandler film is the ultimate meet-cute, love at first sight story. Commitment shy oceanarium veterinarian Harry Roth (Adam Sandler in his warmer, kinder style) only ever dates tourists visiting Oahu in Hawaii … until he meets restaurant owner’s daughter Lucy Whitmore (a charmingly eccentric Drew Barrymore), an artist.

Lucy was in a car accident and she has a form of Hollywood amnesia that erases everything she’s experienced since the accident when she goes to sleep. Ignoring her father’s warnings, Harry then sets up a whole string of cute and kooky “first” meetings (one of which nearly gets a penguin run over) and cute dates with Lucy, gets to know her and falls deeply in love. Harry starts to realise that Lucy might remember more than she is aware of, and works on being a man she could fall in love with for good.

The best bits: The dating and kissing montages are swoon-worthy, but nothing beats a date when your guy takes you to meet his BFF, who is a real-life performing walrus. All this, and you get to see Drew Barrymore beat the heck out of Rob Schneider with a baseball bat – the ultimate first date activity.

Notable quotable: “Nothing beats a first kiss.” – Lucy, many, many times

The Holiday

The Holiday is on Showmax

Nancy Meyers strikes again in this 2006, double couple, house swapping delight. Both fleeing heartbreak, British society columnist Iris (Kate Winslet) and LA-based movie trailer producer Amanda (Cameron Diaz) exchange houses over the Christmas holidays via a website. While revelling in their new surroundings, the two also take a chance on love, Amanda with Iris’s brother Graham (Jude Law), and Iris with Miles (Jack Black), a colleague of Amanda’s ex-boyfriend.

The best bits: Each woman’s house is an ultimate Airbnb fantasy. Iris’s little cottage is charming cosy in a snowy winter wonderland. And Amanda’s palatial modern pad has all the glitz and glam of sunny LA – including Old Hollywood famous neighbours. Iris’s speech about the tragedy of unrequited love is something to pause on. Plus, thanks to old Hollywood character Arthur (Eli Wallach), The Holiday also becomes a movie about the romantic comedy itself, and how to escape the best friend role to become the leading lady.

Notable quotable: “I’m sorry. I didn’t mean to kiss you twice… and then linger a long time on the second kiss.” – Miles

About Time

About Time is on Showmax

This 2013 Richard Curtis fantasy romcom is a modern classic about second chances. Like Palm Springs and 50 First Dates, the story uses the idea of resetting and replaying time to fine tune a relationship until everything is perfect. When Tim (Domhnall Gleeson) falls for his sister’s visiting friend Charlotte (Margot Robbie), he uses his family’s ability to go back in time to try to court her, only to be rejected. Later and older, but no wiser, he uses his time trick to set up the perfect meeting with Mary (Rachel McAdams). The two marry and have kids, and Tim finds out that he can’t change past events before the birth of a child without potentially undoing the child’s existence. In the end, the story is about how wonderfully perfect ordinary life, parenthood and love are. Prepare for happy tears.

The best bits: It’s Richard Curtis, so the side characters knock it out of the park. Tim’s flatmate Harry (Tom Hollander), an angry playwright, tells a fan at a wedding, “I’m here to celebrate true love not scribble my illegible signature on stupid bits of paper that you can flog on eBay so that at the next wedding you can wear a less hideous hat.” And Tim’s mom reminisces about him, saying, “You were such an ugly baby. More chimpanzee than child. I remember the first time I saw you, I thanked God we were within driving distance of London Zoo.”

Notable quotable: “I just try to live every day as if I’ve deliberately come back to this one day, to enjoy it, as if it was the full final day of my extraordinary, ordinary life.” – Tim

The Big Sick

The Big Sick on Showmax

Kumail Nanjiani and his wife Emily V Gordon co-wrote one of the best-ever modern romcoms, inspired by events in their own lives. This 2017 film revolves around stand-up comedian and Uber driver Kumail (Kumail Nanjiani), whose mom is trying to set him up with an arranged marriage. But he’s slowly falling for a former passenger and supposed one-night stand, Emily (Zoe Kazan). Emily finds out about the arranged marriage and breaks up with him, but when she falls ill, Kumail refuses to leave her while she’s in hospital, and the events that follow cement his commitment to her. She’s in a coma, though, and has to catch up with their romance once she wakes up.

The best bits: While the romance is incredibly moving, the laughs keeps us coming back thanks to real life comedians like Ray Romano (as Emily’s father, Terry) and Bo Burnham (CJ). Terry bumblingly asks how Kumail (a Muslim man with Pakistani roots) feels about 9/11, and Kumail tells him, “What’s my stance on 9/11? Oh um, anti. It was a tragedy, I mean we lost 19 of our best guys.” And there are great little bits around the fact that Kumail is an Uber driver, so after he and Emily hook up and she calls an Uber for her walk of shame, Kumail immediately picks up the request and drives her home.

Notable quotable: “You look great. What’s your blood oxygen level?”– Kumail to Emily


Trainwreck with Amy Schumer is on Showmax

Get ready for a wildcard. This 2015 film was written by and stars Amy Schumer as magazine writer Amy, party girl and queen of the one-night stand. She meets her unlikely match when she’s sent to interview Dr Aaron Conners (Bill Hader, writer-creator-director of dark hitman comedy series Barry) – a sports medicine specialist whose clients (and friends) include basketball megastar LeBron James. It’s a switcheroo of the normal formula from producer-director Judd Apatow (Knocked Up, The 40-Year-Old Virgin), with Amy taking on the role of the laid back, slobby, free spirited commitment shy disaster magnet half of the couple and Bill taking on the role of the nerdy workaholic professional who becomes fascinated, compelled and captivated by this trainwreck of a human being. Look out for a hilarious John Cena as Amy’s boyfriend Steven, and Tilda Swinton as Amy’s boss Dianna. 

The best bits: There’s loads of romantic flair in this tale of loving flawed people, including a grand apology scene involving gymnastics in high heels. But it’s a standout when Amy asks her sister Kim whether she deliberately dresses her husband like a guy who teaches computer skills in a church basement so that no one else will want to have sex with him. And if you’ve ever wanted to murder people for talking in the cinema, just watch Steven trying to stand up for Amy when everyone gets annoyed with her. 

Notable quotable: “I like him so much. Why do I feel so scared?” – Amy


Shrek is on Showmax
Image: NBC

No, don’t leave! This animated takedown of Disney Princess stories really is one of the all-time great romantic comedies as Shrek the ogre (Mike Myers) and cursed princess in a tower Fiona (Cameron Diaz) fall in love with all of each other’s onion-like layers of personality. While the things that Fiona wants, does, and thinks make her a monster in the human world, in Shrek’s eyes she’s perfect. It’s not a love at first sight deal, but something they slowly discover during their “road trip” back to her future kingdom. The two go on to explore their love, family and parenthood in Shrek 2 and Shrek The Third.

The best bits: The scenes after Fiona destroys a group of soldiers and pulls an arrow out of Shrek’s bottom is a total hearts and flowers moment. Shrek helps Fiona to cross a river, and when he’s plagued by flies, she catches and wraps them all up in a spider web until she’s able to present them to him like a disgusting stick of candyfloss. Then, using their ogre breath, they inflate a frog and a snake and frolic in a meadow like best friends at a funfair. And Lord Farquaad is the perfect “other” man in the love triangle, because we don’t feel sorry for him at all.

Notable quotable: “I don’t understand. I’m supposed to be beautiful.” – Fiona. “But you are beautiful.” – Shrek (after Fiona’s transformation)

This is just the tip of love’s iceberg on Showmax. Look out for more romantic comedy titles coming your way in this month like George Clooney and Julia Roberts’ Ticket To Paradise and License To Wed with Robin Williams, Mandy Moore and John Krasinski.