2021 Valentine’s Day Rom-Com Picks

So out of the gate I have a confession. I hate Valentines Day.

I’ve never been a fan, I think it’s ridiculously commercial, and over the years I’ve had many friends cry on my couch. It makes people feel bad about being single, it sets outrageous expectations for couples, and it’s hardly ever what you want it to be.

However. Over the years I have crafted my perfect Valentines Day. I always get a fancy pint of ice cream. Something *special*. This year I’m going to pop over to Mables and get some Death In Venice Gelato. Then I get a bunch of blankets, gather everything I need on the couch, and then I eat my ice cream and watch my favourite Rom-Coms. It’s great.

I deeply love a rom-com. It is my favourite genre of movie – but it has to be done well. I dislike Hallmark style ‘Movies of the Week’. I want high quality Nancy Meyers movies. I want movies with big celebrities and movies with fantastic soundtracks. I want smart writing and clever uses of familiar troupes.

Up first and always at the top of the list for Valentines Day is the movie Valentines Day. I wrote a very long blog post about a two years ago and it stands up. 10/10 must watch.

But then once I’m done that I reach for something else. To help you curate your rom-com movie marathon this weekend hopefully this will help. Pick a few from each category and you’ll be set for a great weekend.

90s/00s Mega Hits

I have seen all of these next few movies countless times. You probably have favourites that are not on this list because this was the golden age of Rom-Coms. So many were made and they all slapped. I wish we were putting out movies like this now but the industry has changed. They are no longer making ‘mid-budget’ movies – everything is an indy film or a big budget superhero movie. So let’s dive into a simpler time with some of the classics.

How to Lose a Guy in 10 Days  – Netflix  
A true classic staring Kate Hudson and Matthew McConaughey. She’s writing an article about “How To Lose a Guy in 10 Days”, he’s trying to win a bet that he can get any girl to fall in love with him by a particular party. Hilarity ensues. I always laugh watching this movie which we could all use right now.

Bridget Jone’s Diary  – Netflix
A British classic, It’s a modern retelling of Pride and Prejudice staring Renée Zellweger, Colin Firth, and Hugh Grant. There are three movies in this series so you could really settle in for a marathon. This scene might particular resonate this year…

Anything by Nancy Meyers – Various
You know Nancy. She’s directed hits like It’s Complicated, The Holiday, and The Intern. She is my favourite director and her movies are all incredible. She is the queen of the Rom-Com and also… kitchens.

Clueless – Netflix
A modern retelling of Emma staring Alicia Silverstone, Stacey Dash, Brittany Murphy and Paul Rudd among others. It is a classic. It was number 8 on my top 25 high school movies.

Legally Blonde – Netflix 
You think it’s a love story between Elle and Warren, but it ends up being a self love story. I’m currently studying the GMAT and Elle is my role model. It’s always a winner.

The Wedding Planner  – Netflix
Again, it’s just a classic and stars the incomparable Jennifer Lopez and Matthew McConaughey who both look the exact same 20+ years later. Plus Alex from Grey’s.

10 Things I Hate About You – Disney+
This is one of my ‘I can never overwatch this movie’ movies. It is brilliant. It’s a modern retelling of Taming of the Shrew. Lots of fun, very feminist. The cast is fantastic, the writing is smart, and it aged well. It was number 3 on my HS list. But let’s be honest… we’re all just watching it for this scene.

My Best Friend’s Wedding – Amazon  – 
I love Julia Roberts in this. Here’s the deal – Julia and Dermot Mulroney decide that if they are not married by 28, they’ll marry each other. I’m 29. I get it, but also… like maybe push it to 35. HOWEVER – I understand why Julia freaked out when she found out Dermot wanted to marry college student Cameron Diaz. If any of my friends said they were marrying someone still in university there would be a conversation. I’m into this movie.

My Big Fat Greek Wedding  
So many of my favourite movies are from ‘away’, but this is a ‘made in Toronto’ movie and I adore it for that. It’s such a fun romcom, I owned this on VHS as a kid and would watch it all the time. I have no idea where it’s streaming, but it’s worth renting.

She’s The Man  
A hilarious retelling of Twelfth Night. This is PEAK Amanda Bynes. It’s so quote-able. It’s one of those movies that feels like a warm hug – just instant nostalgia for 00s teens. Get some gouda and settle in.

Pride and Prejudice (the Keira Knightly version) – Crave
I cannot say enough good things about this movie. Everything is perfect. The soundtrack, the acting, the locations, the writing. Just pure perfection. This is a great movie to watch with a cup of tea on a Sunday afternoon. Perfect for this weekend.

Others I’ll endorse:

You’ve Got Mail, Never Been Kissed, Notting Hill, What a Girl Wants, 13 Going on 30, A Cinderella Story, The Prince and Me, Hitch, The Notebook, P.S. I Love You, 27 Dresses, Music and Lyrics, What Happens in Vegas, and The Proposal.


Enter the new rom-coms. These all came out in the last 10 years and you can tell because people have cell phones. A lot of these movies were made for streaming services rather than theatrical releases because of the shift in the way movies are being made. We’ve had some solid rom-coms in the last few years, but I’d argue that Hollywood is only producing one or two a year unlike 2004 that had a SOLID rom-com every other week. So when they do have a smash, these movies are incredible. It’s also worth noting that many of the Contemporary movies are not exclusively about straight white people, which is so refreshing because let’s be real – everyone deserves a love story.

Love, Simon – (coming very soon to Disney+)
This is my favourite of the new rom-coms. I love how it’s from a male perspective which is rare in romantic movies. I think it’s so smart, the soundtrack is amazing, and it’s just feels incredibly authentic. Huge fan of this cast, huge fan of this movie.

Crazy Stupid Love – Netflix
If you’ve never seen this movie, don’t look it up. Just watch it. It’s a movie somewhat like Love Actually with lots of different story line and it’s just so well constructed. It’s written by the guy who created This Is Us and has an all star cast: Ryan Gosling, Emma Stone, Steve Carell, Julianne Moore, and Kevin Bacon. I love this movie. Perfect for a rainy night.

To All The Boys I loved Before  – Netflix
This is probably one of the best RomComs in the last few years. It’s a must-watch in the modern era. I wrote a long blog about my love for this movie so go check that out. But basically we watch this for Peter Kavinsky.

Always Be My Maybe – Netflix
This is a really easy watch with a great cast. Ali Wong and Randall Park star in this, but they also wrote this movie. I think we all have that one person you’re inexplicably tied to and this movie explores that beautifully.

Someone Great – Netflix
So this a breakup film but a *perfect* breakup film. It’s thank u, next in a a movie. I love that the writer/director Jennifer Kaytin Robinson wrote this after being inspired by Taylor Swift’s 1989 and then after watching this movie, Taylor Swift wrote Death By A Thousand Cuts for Lover. It’s perfect. If you are feeling ‘anti-love’ this Valentines Day, this might be your pick. Read my full blog about this movie here.

Set it Up – Netflix
Two assistants try to set their bosses up. It’s very fun. There is pizza. It’s a great movie for people in their 20s just trying to do their jobs and fall in love. Did I have a crush on Glen Powell after watching this… yes. Also co-staring Zoey Deutch, Taye Diggs, and Lucy Liu. 

The F Word – CBC Gem
This is set in Toronto and written by a Canadian writer! In 2021 we’re all about supporting local and this is a great way to do it! You will probably recognize a lot of the locations, but it also might make you sad you can’t go play ping pong at Spin. This stars Harry Potter himself, Mr Daniel Radcliffe opposite Zoe Kazan.

Crazy Rich Asians
Quite possibly one of the best Rom Coms EVER. It is a fantastic movie based on an amazing book series. This was one of the few big budget rom-coms of the past 10 years and it shows. It had a $30 million production budget but made $239 million globally at the box office. I could watch this movie on repeat – it’s so good.

The Fault in our Stars – Disney+ 
Based on the book by John Green (if you don’t know him, google him. He and his brother Hank are fantastic), this a story about two teens with cancer who fall in love. 100% it will make you cry which maybe you need right now. Just let it all go. Staring Aaron Roger’s new fiancée(?!) Shailene Woodley and Ansel Elgort – it’s a great teen rom-com.

Others I’ll endorse:

Life As We Know It, When in Rome, That Awkward Moment, The Big Sick, Long Shot, and LaLa Land.

Bonus – Rom-Com TV shows

Four Weddings and a Funeral – Crave
This is the Mindy Kaling produced mini series rather than the movie. It is a MUST watch. Four American friends trying to find love in London, UK. It’s funny, it’s touching, it’s so well made. It references all the other rom-coms. It’s a 10/10. Please watch this.

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