Timeless movies for the hopeless romantic

Looking for something to watch with your sweetheart on Valentine's Day, or with anyone when you just want a good laugh/cry? You can't go wrong with these.

Meg Ryan and Billy Crystal walking along a sidewalk in the movie When Harry Met Sally Photo: Metro Goldwyn Mayer

I've always been a hopeless romantic. My mother and I have been watching romance movies together since I was very young. We’ve seen the good, the bad and everything in between. Here’s my list of the best movies to watch if you’re looking for a good love story



(Movies that defined the genre and are a must-watch)


Dirty Dancing

Stars: Patrick Swayze, Jennifer Grey

Baby recounts her summer at the Catskills, where she falls in love with a choreographer at her camp, but this forbidden love doesn’t stop her from chasing her dreams. Has one of the most recognizable scenes from the ’80s.


When Harry Met Sally

Stars: Meg Ryan, Billy Crystal

A story focused on the pair Harry and Sally, starting with an argument on whether men and women can ever just be friends. It spans 12 years of their lives until they finally confess their love for each other. This has one of my favourite “confessions of love” speeches in a romance.


27 Dresses

Stars: Kathrine Heigl, James Marsden

Follows the story of always a bridesmaid, never a bride, as the lead hopeless romantic will bend over backwards to make sure all her friends have the perfect wedding. She finally gets her chance to fall in love with a newspaper writer, containing one of the most cathartic movie endings.


13 Going on 30

Stars: Jenifer Garner, Mark Ruffalo

After Jenna wishes to be 30, she’s transported to the future and has to discover what happened in her life and reconnect with her childhood best friend. They rekindle the spark they didn't realize they had. Contains a great dance scene.


Sad romances

(For those looking to cry their eyes out)


A Walk to Remember

Stars: Mandy Moore, Shane West

It starts off as a sweet rom-com for teens that quickly turns into a dilemma about life and what to do with the time you have left. Definitely not recommended for those who want a happy ending.


Love, Rosie

Stars: Lily Collins, Sam Claflin

Follows characters Rosie and Alex who are friends for most of their lives in a “will they won't they/never being able to find the right time” story. They always seem to miss each other by one big event after the other. It really shows that timing is everything.


Me Before You

Stars: Sam Claflin, Emilia Clarke

Follows Louisa, a caretaker who starts working for William, a man in a wheelchair. One of the purest forms of love captured on a movie screen but one of the most devastating endings, so be prepared to ball your eyes out.


The Fault in our Stars

Stars: Shane Woodley, Ansel Elgort 

Hazel and Augustus find each other in a cancer support group—one is terminally ill and the other has recovered. During Hazel's final days, they decide to spend their little time together discovering the meaning of life and also what they mean to each other.


About Time

Stars: Rachel McAdams, Domhnall Gleeson

At 21, Tim discovers that all the men in his family can time travel, and he uses his powers to try to fix all the mistakes that he’s made, including all of his attempts to win over the love of his life, Mary.



(For those who want a good laugh with their heartwarming story)


She’s the Man

Stars: Amanda Bynes, Channing Tatum

In a modern telling of Twelfth Night, Viola dresses up as a man to be able to join the boys' soccer team and develops a strong friendship with Duke. As the movie goes on, the love between them becomes apparent and the hijinks become crazier than ever before.


The Holiday

Stars: Jack Black, Kate Winslet, Cameron Diaz, Jude Law

Feeling dejected with their lives, Amanda and Iris switch houses for the holiday, only for them both to find love in the city they’ve travelled to. This is the perfect Christmas movie that gives double the romance of a normal rom-com.


She’s All That

Stars: Freddy Prince Jr., Rachael Leigh Cook

A classic high school rom-com where Zack bets that he can make Laney prom queen. While doing so, in typical rom-com fashion, the two end up falling in love, creating a heartfelt bond between the two of them.


Home Again

Stars: Reese Witherspoon, Pico Alexander

After a supposed one-night stand with a younger man, Alice's family grows attached to Harry and his friends, and they all become a blended family. This is a heartwarming story about family and chasing your dreams.


Just Go With It

Stars: Jennifer Aniston, Adam Sandler

While Daniel tries to get Palmer to fall in love with him, she finds a ring in his pocket. Now he has to try to convince his assistant Kathrine to pretend to be his ex-wife so he can dupe the girl into falling in love with him, but realizes his assistant was the one all along.


My personal favourites


10 Things I Hate About You

Stars: Julia Stiles, Heath Ledger

Bianca Stratford is one of the most coveted girls in school, the only problem is she isn’t allowed to date until her sister Kat does. Patrick is being paid to take out Kat, but he quickly realizes he has fallen for her. It’s a classic high school romance that never goes out of style with a hilarious star-studded cast.


Set it up

Stars: Glen Powell, Zoey Deutch

Two assistants, Harper and Charlie, are tired of their bosses always being so demanding of their work, so they decide to get their two bosses together. But in the process they end up falling in love themselves. It’s a hilarious movie that shows the natural and endearing development of their love story. It also has Pete Davidson in a supporting role.


Little Women (2019)

Stars: Saoirse Ronan, Florence Pugh, Timothée Chalamet

While many would first think of the romance of Jo and Laurie in this classic story, the 2019 version focuses on the sweet relationship between Amy and Laurie. Taking a deep dive into their romantic development, it finally gets audiences to root for this couple.