20 Best Romantic Movies of My Time

With all the hard work that we do on the daily, we sometimes need and deserve a break. I’m a big movie buff and love watching a good movie any chance I get. In my teen years, I worked at Blockbuster Video, which by the way I truly miss the concept of video stores. I used to walk the aisles after my shift and pick out rom coms and watch them sometimes through the night. I’m a sucker for fairytale endings. Life is much different now. I have a household full of boys so I usually am outnumbered with what we watch. It’s mostly animated, action, or superhero movies, which are perfectly fine. I usually enjoy them, too. HOWEVER, many times I am in desparate need of a good chick flick. So in the rare occurance I have some time to myself, I will watch one of my favorites. I am a hopeless romantic. I LOVE a good love story and if its a great one, I really get carried away by it. Romantic comedies are my favorite genre, but there are just so many good love stories out there that I can watch over and over and over again.

I want to share with you my list of the 20 best romantic movies of my time. I am pretty picky about my movies. I have to be thoroughly entertained and really vested in the characters and story, so if a movie made my list, then its one that swept me off my feet and made me want to live happily ever after with my prince charming.

Please note that I left out true classics like Dirty Dancing and Pretty Woman. I love those movies dearly, but I’m going under the assumption that you’ve already seen those (because who hasn’t) many times over.

So, if you get any free time, mamas, and in need of a good movie to watch, this list is for you.

In no particular order:

1. The Longest Ride

Holy cowboy, ladies. This is one heck of a movie, y’all! Not only do you get 2 beautiful love stories in one movie, but the eye candy is just off the charts. The movie is based off of the book written by none other than Nicholas Sparks. Same author of The Notebook, so you know its going to be a doozy. The cowboy in this very entertaining movie is played by Scott Eastwood, the son of Clint Eastwood who is the ultimate cowboy. The movie is about two very different lives that come together in strange circumstances and fight all odds to be together. It has a very Tale of Two Cities feel to it. So, go ahead ladies, let Mr. Eastwood, make your day.

2. P.S. I Love You

Well this one has all the feels. An emoitonal rollercoaster portrayed beautifully by Hillary Swank. The men in this movie are perfect, Gerard Butler, Jeffrey Dean Morgan, and Harry Connick, Jr. give stellar performances and are super easy on the eyes. Although the love story is a sad one, I love the unique concept of conveying a love everlasting despite tragic circumstances. It gives you hope in love and that it transcends all barriers and obstacles, even in death. I love this movie, and if nothing else, just for Gerard Butler’s delicious Irish accent.

3. The Holiday

This is the cutest of all the movies on the list. This is another one that has two love stories in one, so you get a double whammy. Cameron Diaz and Kate Winslet are thwarted in their respective relationships. They set out on a quest to find themselves and in the process meet people that forever change their lives and their outlook on life. The stories are cute and the characters loveable, including Jack Black and Jude Law and three very precious little girls. This is one of my very favorites to watch every Christmas, but you can enjoy it just the same any time of the year.

4. Safe Haven

This romantic drama has a good mix of suspense, drama, and romance. The movie is based off of another Nicholas Sparks book. Katie, played by Julianne Hough, escapes her past to find safe haven in a small remote town, where she meets Alex, played by Josh Duhamel, and his kids. This movie is about second chances and starting over. She’s been running from her past, but when her past comes looking for her, Alex helps her face it head on. Now, I will say, that I’m a pretty good guesser of movie endings. Most of them, while enjoyable, are predictable. This movie has a plot twist that had me completely surprised. I love when a movie pulls the rug from under me and gives me a good gasp.

5. The Wedding Date

This one is kind of a Pretty Woman-esque movie, but this time the man is the escort instead of the woman. Kat, played by Debra Messing, pays for an escort to accompany her to her sister’s wedding as her boyfriend to make an ex-boyfriend jealous. Her plan backfires as she starts to have feelings for her male escort, played by a very charming Dermot Mulroney.

6. How to Lose a Guy in 10 Days

I love the dynamic between Kate Hudson and Matthew McConaughey so much so that it had me wishing they were together in real life. So, this movie is quite cheesy, but I loved it anyway and have watched it numerous times. I love the storyline and how these 2 met under false pretenses only to find something more real in the process. Kate Hudson is purposely annoying in the movie and it makes it more endearing. Matthew is just great on all levels and he plays the perfect male lead. Insert swoon here.

7. The Wedding Planner

I hate to admit it, but I’m a sucker for J-Lo movies. I’m also a sucker for Matthew McConaughey as you can probably tell by now. This is a very cute movie about two people who can’t fall in love because of their circumstances, but still do. Their chemistry is off the charts and they can’t run away from it although they try. Another cheeseball movie, that I highly recommend.

8. Maid in Manhattan

Yep! Another J-Lo movie…hee hee. I love a good cinderella story and this is one of them. Only this one has a unique way of portraying the fairytale. The characters are loveable, especially her cute son who plays a big part in her finding her prince charming. I love the mom and son dynamic in this movie, too.

9. Love Actually

Several intertwined stories examine the complexities of the one emotion that connects us all: LOVE. Among the characters are David (Hugh Grant), the handsome newly elected British prime minister who falls for a young junior staffer (Martine McCutcheon), Sarah (Laura Linney), a graphic designer whose devotion to her mentally ill brother complicates her love life, and Harry (Alan Rickman), a married man tempted by his attractive new secretary. Perhaps the most endearing love story is of a very young boy who falls in love with a young girl and goes to extreme lengths to let her know.

10. Something’s Gotta Give
When an old womanizer Harry Sanborn played by Jack Nicholson, and his young girlfriend, Marin, Amanda Peet, arrive at her family’s beach house in the Hamptons, they find that her mother, author and playwright Erica Barry, Diane Keaton, also plans to stay for the weekend. Erica is scandalized by the relationship and Harry’s sexist ways. But when Harry has a heart attack, and a doctor, Keanu Reeves, prescribes bed rest at the Barry home, he finds himself falling for Erica — who, for once, may be out of his league. I love Diane Keaton! I love how the relationship between her and Harry plays out and when she takes us through the realistic emotions of a break up, its not only sad but very funny.

11. A Walk to Remember
A Walk to Remember is a movie to remember. Such a sweet love story between 2 teens who are very different, but discover that they have more in common than they realized. Its a movie that inspires and gives you hope in God and the healing power of love. It has a plot twist that changes everything and changes their lives forever.

12. Failure to Launch
This one is a very quirky movie and the storyline is interesting, although very peculiar. It has its fair share of slapstick comedy and cheesiness, but I enjoyed it. Sometimes you have to take movies for what they are, and this one is a corny, funny, and likeable love story portrayed by one of my faves, Sarah Jessica Parker, and one of my main men, Matthew McConaughey.

13. A Fault in our Stars
Hazel Grace Lancaster (Shailene Woodley), a 16-year-old cancer patient, meets and falls in love with Gus Waters (Ansel Elgort), a similarly afflicted teen from her cancer support group. Hazel feels that Gus really understands her. They both share the same wit and a love of books, especially Grace’s touchstone, “An Imperial Affliction” by Peter Van Houten. When Gus scores an invitation to meet the reclusive author, he and Hazel embark on the adventure of their brief lives.

14. The Vow
Paige, played by one of my faves, Rachel McAdamsm and Leo, played by Channing Tatum, are happily married newlyweds, but their beautiful life together is shattered when a car accident leaves her in a coma. When Paige awakes, she has severe memory loss and doesn’t know Leo. She also has a confusing relationship with her parents and still harbors feelings for a former fiance. Despite these difficult obstacles, Leo is determined to renew their bond and rebuild their marriage. I love how true this is to the saying that if you love someone, you have to let them go. What’s meant to be will be.

15. The Notebook
What can I say about this love story. It’s just beautifully written and the characters played by Rachel McAdams and Ryan Goseling are simply perfect. Everyone wants someone to grow old with and this movie fights for that. Through all the struggles and obstacles and all of the heartache endured, love conquers all.

16. The Family Stone
This is another one I love watching at Christmas, but its such a beautiful story and has many different love stories. The relationships between family, siblings, boyfriends, fiances, lovers….it just has so many stories to fall in love with. The heart of the movie ends up being a heartbreaking one, but one that brings them all together despite the oh so many conflicts. My favorite actresses are also in the movie, Diane Keaton, Rachel McAdams, and Sarah Jessica Parker. Grab your tissues for this one, moms.

17. Serendipity
I am a believer in fate and destiny, which is why I love this movie. On a magical night, Jonathan (John Cusack) meets Sara (Kate Beckinsale). He finds it was love at first sight, but Sara believes in destiny. After 10 years the two, with 3,000 miles between them, must decide if fate wants them to be together again. When love feels like magic, it is called destiny; when destiny has a sense of humor, it is serendipity.

18. Sleepless in Seattle

A classic. The dynamic of Meg Ryan and Tom Hanks is one of my favorites of all time. After the death of his wife, Sam Baldwin (Tom Hanks) moves to Seattle with his son, Jonah. When Jonah calls in to a talk-radio program to find a new wife for his father, Sam grudgingly gets on the line to discuss his feelings. Annie Reed (Meg Ryan), a reporter in Baltimore, hears Sam speak and falls for him, even though she is engaged. Unsure where it will lead, she writes Sam a letter asking him to meet her at the Empire State Building on Valentine’s Day.

19. You’ve Got Mail

A modern day remake of Sleepless in Seattle. I love the remake and just as cute as the original. I love the characters and again Meg and Tom’s dynamic is the best. Struggling boutique bookseller Kathleen Kelly (Meg Ryan) hates Joe Fox (Tom Hanks), the owner of a corporate Foxbooks chain store that just moved in across the street. When they meet online, however, they begin an intense and anonymous Internet romance, oblivious of each other’s true identity. Eventually Joe learns that the enchanting woman he’s involved with is actually his business rival. He must now struggle to reconcile his real-life dislike for her with the cyber love he’s come to feel.

20. When Harry Met Sally

An oldie, but a goodie. In 1977, college graduates Harry Burns (Billy Crystal) and Sally Albright (Meg Ryan) share a contentious car ride from Chicago to New York, during which they argue about whether men and women can ever truly be strictly platonic friends. Ten years later, Harry and Sally meet again at a bookstore, and in the company of their respective best friends, attempt to stay friends without sex becoming an issue between them.

I know there are many, MANY missing from this list, but I’ll leave at it these for now. Watch them, fall in love, and get swept off your feet as I did. What are some of your favorites? Comment below!


  1. Lindsey

    Such a good list!! The only one I haven’t seen is The Longest Ride…I need to get on that!


  2. Lindsey

    Such a good list!! The only one I haven’t seen is The Longest Ride…I need to get on that!


  3. Chrissie

    Oh my gosh, such a great list! I think every single one of my favorite movies is on here.


  4. ohmummymia

    Wow I can see couple of my fav movies on your list. Def I want to see Safe Haven


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