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Valentine’s Movies to Watch

Happy Valentine’s Day!! I swear the holidays were just yesterday, where does the time go? I don’t know about you, but a classic rom-com at the end of the day is a Valentine’s Day tradition for me! Even if I go out to dinner, I always come home and watch a classic movie. When I sat down to think about what I want to watch this year, I realized that the possibilities are endless. There are older, classic movies, movies from the 90’s, early 2000’s and of course, the newer romantic comedies. How is anyone supposed to decide?! Do you ever go to watch a movie and end up taking like thirty minutes to decide? At that point, I could be halfway through a film! I put together a list of the very best movies I could think of in hopes to help make your movie choices easier tonight.

Happy Valentine’s Day, my friends!

Valentine’s Day

Let’s start with the movie with today’s title! Is it cheesy? Yes, but do I love it? Yes! If you haven’t seen this film, it is an all star cast and follows the story of several people’s lives on Valentine’s Day. Everyone’s paths are woven and somehow they all connect, which I think is really cool when writers do that.

Crazy, Stupid, Love

This is a favorite of mine! It’s another movie that has a great cast of actors and when I tell you I can’t get enough of it– I could watch it a million times. It’s all about a few people who fall in and out of love, and like the previous film, everyone’s stories are somehow related, which is always a fun surprise.

When Harry Met Sally

Talk about classic films, this is up there! Harry and Sally share a long car ride where they argue about whether or not guys and girls can just be friends. 10 years later, they find each other again in a bookstore and once again, they find that just remaining friends is difficult for the two of them. It’s a very well known film with amazing stars, I highly recommend!

50 First Dates

I have to be honest, I love this film, but I do get emotional over it! That’s not a bad thing, though. Henry falls for Lucy, but she has short-term memory loss, so every single day he has to “meet” her and woo her all over again. It really is such a sweet concept and, obviously the cast is great! I think that goes for all of these movies.

Pretty Woman

A classic bizarre Cinderella twist of people who aren’t supposed to be together; a prostitute and businessman fall in love. Starring Julia Roberts and Richard Gere, can these two bridge the gap between the extremely different worlds they live in?

The Notebook

Another one that makes me cry, but seriously hard. Based on the Nicholas Sparks book, two people fall in love, but it’s not easy. With the help of the narrator, we watch the story of the lovers unfold as her parents disapprove and he goes off to fight in WWII. Will he return and what will happen? Bring your tissues and chocolates, you’ll need them!

Crazy Rich Asians

This is a favorite film of mine, I can’t get enough of it! Rachel is meeting Nick’s family for a wedding in Singapore. There’s just a few problems beginning with the fact that she had no idea he was loaded and the family doesn’t like her. We’ve seen this type of story before, but this one is hilarious, glamorous and a little heart breaking. It is well done in every single way, and you will want to watch to find out what happens.

The Proposal

A major book editor is getting deported, so she makes her assistant pretend to be her fiance, to keep her in the states a little longer. She must go on a trip with him back home to Alaska from NYC for his Gammy’s birthday. Somewhere along the way, this lie becomes a reality and they now have to prove to everyone, including deportation that they are in love– for real.

How to Lose a Guy in 10 Days

Kate Hudson and Matthew McConaughey fans, if you haven’t seen this, what are you doing? A girl sets up the story to prove that she can get a guy to leave in 10 days, while the man is trying to prove he can get a girl to fall in love with him in 10 days. Who is right here? Are both wrong?

P.S. I Love You

Holly’s husband passes away, but not without leaving a few surprises for her. On her 30th birthday she wakes up to the first letter in the series he has written for her. She learns how to mourn, deal with grief and return to life again, with the help of her late husband. Another tear jerker, but a classic!

To All the Boys I’ve Loved

If you have teens, this is the movie–I mean, series you need to watch. It’s based off a book series that follows Lara Jean, who wrote her crushes love letters as a kid. But when someone sends them out her sophomore year of high school, she now has to deal with the repercussions of writing them in the first place. A series of events unfold and she has to fake a relationship with one of her crushes. Is there a line and will they cross it?

Sleepless in Seattle

After the death of his wife, Sam moves to Seattle with his son. One day, his son calls into the local radio station to find a wife for his dad and he is forced to get on the phone and talk. A reporter hears him and falls in love with him over the radio. She is engaged and unsure of what to do, so she writes to him and asks him to meet her at the Empire State Building on Valentine’s Day.

500 Days of Summer

I’ve heard people say this movie is an acquired taste, and I sorta see it, but I do really enjoy it. I think it’s very different from any other rom-com I’ve seen. A greeting-card writer is completely taken back when his girlfriend breaks up with him. He looks back on their 500 days together to try to piece together where they went wrong. Through doing so, he rediscovers his passions.

About Time

I love a good Nicholas Sparks film! This one is all about time travel, which is pretty cool. Tim and his father are both time travelers, which is both awesome and scary. What’s scary about it, is that every time they go back in time, it changes things and not everything works out how it was supposed to. Can Tim figure out the balance between the here and now and the past?

Love Actually

Saving the best for last, this movie has all the feels. This is another one with intertwined love stories, but honestly, it’s the very best. If you’ve seen this, you know the scene with the cards and music– just gets to me. I can’t rave about the cast enough and the story gets so complicated, yet it’s very simple. It shows you that you can find love, everywhere.

For more recommendations on things to watch, visit here!

This post was originally published February 14th, 2022*

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16 thoughts on “Valentine’s Movies to Watch”

  1. This is such a fun post – perfect timing for Valentine’s Day! I love having a cozy movie night for the holiday. Great list of movies!

  2. Awww The Notebook. I remember my late granny and I watching that. She loved it and thought it was so romantic! I can’t even look at it now without getting tearful. I also love The Lakehouse. Very niche one but beautiful all the same.

  3. Valentine’s movies are so special because they evoke various emotions, from laughter and joy to tears and nostalgia. They can bring people closer together by creating a shared experience that is both memorable and meaningful. My Best Friend Wedding is one of my favourite movies of all time.

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