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Back in my youth, I was someone who scowled at Valentine’s Day – you’re supposed to love the one you’re with every day! Ah, to be young, single… and bitter. Since then, I’ve come to the conclusion that Valentine’s Day can be as special or insignificant as you choose, but why complain over free chocolate and flowers? I’m not that strong, myself.

Besides gifts, the main theme behind Valentine’s Day is, of course, romance. I’ve been into classic films since high school, and yes, have made every man in my life sit through at least one black and white movie with me on Valentine’s Day.

Now, boyfriends have come and gone, but my love for classic films is still alive and well, so I have compiled a list of my absolute favourite romantic old movies for you to watch with your partner. If they’re not interested in delving into Old Hollywood with you on February 14th, I highly suggest using, “So what, you don’t love me?!” tactics until they’ve succumbed.

Moving along. In no particular order:

An Affair to Remember

Starring: Cary Grant, Deborah Kerr

Directed by: Leo McCarey

Why you should watch it: Deborah Kerr is all class and smooth Cary Grant oozes his usual charm, with a softer side. This is a gut-wrenching movie with lots of romance. If the title seems vaguely familiar to you, it’s for a reason – this is one of the most popular romance movies of all time. Deborah and Cary fall in love on a cruise despite both being engaged to different people. They make a deal to meet at the Empire State Building in six months if they still believe their love is real. Make sure you have tissues!

Love in the Afternoon

Starring: Audrey Hepburn, Gary Cooper

Directed by: Billy Wilder

Why you should watch it: Besides Alfred Hitchcock, Billy Wilder has to be my favourite classic Hollywood director! All of his films just have a special touch that’s easy to spot but difficult to explain. In Love in the Afternoon, Audrey Hepburn plays a detective’s daughter and let’s just say…Gary Cooper is in trouble. I had read the plot of this film in high school before borrowing the VHS (good times) from the library and was completely hooked. I am a major Audrey Hepburn stan, and in my opinion, this is one of Audrey’s more underrated movies. If you’re a Hepburn fan, definitely pop some bubbly or pour your favourite coffee and spend the night in with this one. I’ve actually only seen this once, so I may have to take my own advice!


Starring: Humphrey Bogart, William Holden, Audrey Hepburn

Directed by: Billy Wilder

Why you should watch it:
One of my favourites I have re-watched time and time again! Bogart and Hepburn are both in my top favourite classic Hollywood actors lists. The story! An ugly duckling grows up to be the belle of the ball and while nursing a crush on the younger of two brothers, gets to know his older brother. This is a movie with pure magic – you can see the sparkles through the black and white! Very romantic and a must-watch. Like Love in the Afternoon, this movie is best enjoyed with black coffee or champagne.


Starring: Humphrey Bogart, Ingrid Bergman

Directed by: Michael Curtiz

Why you should watch it: My sources (a Tumblr post from ten years ago) tell me this movie was never meant to be big but everyone loved the romantic tension between Bogart and Bergman and it became one of the most famous classic films! Bogie is at his best here – tough, romantic, broody, aloof. I do have a bone to pick however, as I’ve heard Rita Hayworth, my favourite classic actress, was considered for the main lead role and I would’ve loved to see her in a movie with Humphrey Bogart! That being said, this wartime movie is still a great one to watch with a partner, and even alone since it’s known to most as one of the greatest films ever made. Bogart is a nightclub owner in Casablanca, minding his business when Bergman, an old flame, visits town with her husband. Watch with gin & tonics or martinis for optimal viewing experience.

Designing Woman

Starring: Lauren Bacall, Gregory Peck

Directed by: Vicente Minnelli

Why you should watch it: Want something light? How about two actors who usually play serious roles being in a romantic comedy? Lots of physical comedy with this one. A designer and a sportswriter get married quite…quickly…and realize they barely know each other. You’ll love seeing these two on screen together! #TallLegends

You’ll Never Get Rich

Starring: Fred Astaire, Rita Hayworth

Directed by: Sidney Lanfield

Why you should watch it: Rita Hayworth is amazing. You already know she’s a favourite of mine. She also said her two movies with Fred Astaire were the jewels of her life, a big reason why both of their films together are on this list. Fred Astaire is more known for his roles with Ginger Rogers but Fred has said Rita was his favourite dance partner! Two of the most graceful dancers, two romance films. Another wartime flick, You’ll Never Get Rich is a lighter film. A Broadway producer is caught buying a gift for Rita by his wife. To take the suspicion off himself, he sets Fred and Rita up on a date. This movie is definitely underrated, and a fun watch. Enjoy!

You Were Never Lovelier

Starring: Fred Astaire, Rita Hayworth

Directed by: William A. Seiter

Why you should watch it: Rita Hayworth at her most beautiful. This film is great because you see her be both charming and petulant, and spoiler alert: it’s very cute. Rita plays a second-oldest daughter who according to her father, must get married before her younger sister. Fred happens to be out of work. This is a light movie that sparkles with romance and laughter. I could watch these two dance all day!

Pillow Talk

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Starring: Doris Day, Rock Hudson

Directed by:
Michael Gordon

Why you should watch it: Goodness, this is a good one! Another light film, with lots of laughs but feel-good, lovey-dovey action too. Rock Hudson is so smooth in this, and Doris Day is absolutely hilarious! The misunderstandings make this movie a gem. Picture it: Doris and Rock share a party phoneline and Doris gets sick of Rock always hogging the phone, with of course, the ladies. Revenge ensues. Definitely enjoy with Bloody Marys.

Dark Passage

Starring: Humphrey Bogart, Lauren Bacall

Directed by: Delmer Daves

Why you should watch it: Lauren Bacall and Humphrey Bogart were actually a couple in real life, and even got married and had kids! Their chemistry vibrates through the screen, and Dark Passage is personally my favourite film they did together. Although this one really falls under film noir, it’s definitely romantic with these two! Bogart escapes prison and tries to clear his name for a crime he didn’t commit. I won’t say anything else but let’s just plastic surgery and Bacall are part of his…healing process.

Roman Holiday

Starring: Audrey Hepburn, Gregory Peck

Directed by: William Wyler

Why you should watch it: Another special Hepburn movie, Roman Holiday is a story about a princess who wants to explore Rome and live like a normal person. Cue Peck – a reporter – who definitely recognizes the princess. This movie is so fun but what endears it to me the most is how genuine both leads are in their roles. Like Sabrina, this movie pulls at your heartstrings. And you’ll definitely cry at the end of the movie – unless you’re a sociopath. Eat with ice cream!

Well? Get to watching!

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