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27 Feel-Good Rom-Coms To Keep You Cozy And Entertained This Winter - Possibility Press
Sunday, May 19, 2024
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27 Feel-Good Rom-Coms to Keep You Cozy and Entertained This Winter

These 27 feel-good rom-coms are sure to keep you cozy and entertained this winter. From classic favorites to new releases, these films are guaranteed to put a smile on your face and warm your heart.

Are you looking for feel-good rom-com recommendations to keep you cozy and entertained this winter? If you are, then you’ve come to the right place.

Winter is here and it’s the perfect time to curl up with a warm blanket, hot cocoa, and a feel-good romantic comedy. Whether you’re single or in a relationship, these rom-coms are sure to keep you cozy and entertained. From classic favorites to newer releases, I’ve compiled a list of 27 must-watch romantic comedies that are sure to brighten up your winter days and nights.

Feel-Good Rom-Coms

From charming and heartwarming to hilarious and witty, these movies are guaranteed to make you laugh, smile, and maybe even fall in love. So, grab your popcorn and get ready for a movie marathon with these 27 feel-good rom-coms to keep you cozy and entertained this winter.


1) You’ve Got Mail

You’ve Got Mail is a 1998 romantic comedy film directed by Nora Ephron starring Tom Hanks and Meg Ryan. The film is about two people, Joe Fox (Hanks) and Kathleen Kelly (Ryan), who are involved in a bitter business rivalry but fall in love anonymously over the internet. The story is a modern retelling of the classic play “Parfumerie” by Hungarian playwright Miklos Laszlo.

Best You’ve Got Mail Movie Quote

Sometimes I wonder about my life. I lead a small life – well, valuable, but small – and sometimes I wonder, do I do it because I like it or because I haven’t been brave? So much of what I see reminds me of something I read in a book, when shouldn’t it be the other way around? I don’t really want an answer. I just want to send this cosmic question out into the void. So good night, dear void. ~ Kathleen Kelly, in an email to NY152

Watch You’ve Got Mail: Amazon | YouTube | Google Play


2) One Fine Day

One Fine Day is a 1996 romantic comedy film directed by Michael Hoffman and starring Michelle Pfeiffer and George Clooney. The film is about two single parents, Melanie Parker (Pfeiffer) and Jack Taylor (Clooney), who have a chance encounter while both trying to juggle their busy careers and taking care of their children. As they spend the day together trying to coordinate the care of their kids, they begin to develop feelings for each other.

Best One Fine Day Movie Quote

Because in the beginning of the relationship when we were choosing up sides, you chose grownup first. ~ Jack Taylor

Watch One Fine Day: Amazon | YouTube | Google Play


3) Serendipity

Serendipity is a 2001 romantic comedy film directed by Peter Chelsom and starring John Cusack and Kate Beckinsale. The film is about two people, Jonathan Trager (Cusack) and Sara Thomas (Beckinsale), who meet by chance in New York City and connect over a mutual love for music and fate. They spend a magical evening together but decide to leave their fate in the hands of serendipity, agreeing to reunite if they are meant to be together. Years later, Jonathan and Sara both find themselves searching for one another, unsure if their love story was meant to be.

Best Serendipity Movie Quote

If you want to improve, be content to be thought foolish and stupid. ~ Dean Kansky

Watch Serendipity: Amazon | YouTube | Google Play


4) The Family Man

The Family Man is a 2000 romantic comedy-drama film directed by Brett Ratner and starring Nicolas Cage and Téa Leoni. The film is about a wealthy Wall Street businessman, Jack Campbell (Cage), who is given the opportunity to see what his life would have been like if he had chosen to marry his college sweetheart, Kate (Leoni), instead of becoming successful in his career. Jack is then transported to an alternate reality where he is married to Kate and has two children and is shocked to find himself living in a modest home in the suburbs and working as a tire salesman. As he lives this new life, he starts to realize the true value of family, love, and happiness.

Best The Family Man Movie Quote

How can you do that? (What? ~ Jack) Look at me like you haven’t seen me every day for the last 13 years. ~ Kate

Watch The Family Man: Amazon | YouTube | Google Play


5) Love Actually

Love Actually is a 2003 romantic comedy film directed by Richard Curtis and starring an ensemble cast including Hugh Grant, Liam Neeson, Colin Firth, Emma Thompson, Keira Knightley, and many others. The film tells multiple interconnected stories about love and relationships in the lead-up to Christmas. The stories include a new Prime Minister who falls for a member of his staff, a married man who begins an affair, and a young boy who is smitten with a girl at school, among others.

Best Love Actually Movie Quote

When the planes hit the Twin Towers, as far as I know, none of the phone calls from the people on board were messages of hate or revenge—they were all messages of love. If you look for it, I’ve got a sneaky feeling you’ll find that love, actually, is all around. ~ Prime Minister

Watch Love Actually: Amazon | YouTube | Google Play


6) Sabrina

Sabrina is a 1995 romantic comedy-drama film directed by Sydney Pollack and starring Harrison Ford, Julia Ormond, and Greg Kinnear. The film is a remake of the 1954 film of the same name and is based on the play “Sabrina Fair” by Samuel Taylor. It tells the story of Sabrina Fairchild (Ormond), the daughter of a wealthy family’s chauffeur, who falls in love with the two sons of her father’s employer, David Larrabee (Kinnear) and Linus Larrabee (Ford). As Sabrina grows up and returns from Paris, she becomes a confident and independent woman, and the Larrabee brothers are forced to confront their feelings for her.

Best Sabrina Movie Quote

Once upon a time, on the north shore of Long Island, not far from New York, there was a very, very large mansion, almost a castle. And on this very large estate lived a small girl. And life was pleasant there and very, very simple. But, then one day, the girl grew up and went beyond the walls of the grounds and found the world. ~ Sabrina

Watch Sabrina: Amazon | YouTube | Google Play


7) The Holiday

The Holiday is a 2006 romantic comedy film directed by Nancy Meyers and starring Cameron Diaz, Kate Winslet, Jude Law, and Jack Black. The film tells the story of two women, Amanda (Diaz) and Iris (Winslet), who decide to swap houses for the holiday season as a way to escape their problems. While in each other’s homes, they both end up falling for the men they meet there, Miles (Black) and Graham (Law).

Best The Holiday Movie Quote

I understand feeling as small and as insignificant as humanly possible. And how it can actually ache in places you didn’t know you had inside you. And it doesn’t matter how many new haircuts you get, or gyms you join, or how many glasses of chardonnay you drink with your girlfriends… you still go to bed every night going over every detail and wonder what you did wrong or how you could have misunderstood. And how in the hell for that brief moment you could think that you were that happy. And sometimes you can even convince yourself that he’ll see the light and show up at your door. And after all that, however long all that may be, you’ll go somewhere new. And you’ll meet people who make you feel worthwhile again. And little pieces of your soul will finally come back. And all that fuzzy stuff, those years of your life that you wasted, that will eventually begin to fade. ~ Iris

Watch The Holiday: Amazon | YouTube | Google Play


8) The Family Stone

The Family Stone is a 2005 romantic comedy-drama film directed by Thomas Bezucha and starring an ensemble cast including Diane Keaton, Rachel McAdams, Craig T. Nelson, Sarah Jessica Parker, Luke Wilson, and others. The film is about an uptight and conservative businesswoman, Meredith Morton (Parker) who is invited to spend Christmas with her boyfriend’s eccentric and free-spirited family, the Stones. As Meredith struggles to win over her boyfriend’s family and fit in, she must also confront her own personal issues and learn to let go of her control.

Best The Family Stone Movie Quote

You were just a little girl in a flannel nightgown. And you were shoveling snow from the walk in front of our house. And I was the snow, I was the snow. And everywhere it landed and everywhere it covered. You scoop me up with a big red shovel. You scoop me up. ~ Ben Stone

Watch The Family Stone: Amazon | YouTube | Google Play


9) The Wedding Planner

The Wedding Planner is a 2001 romantic comedy film directed by Adam Shankman and starring Jennifer Lopez and Matthew McConaughey. The film follows Mary Fiore (Lopez), a successful wedding planner, who falls in love with a groom-to-be, Steve Edison (McConaughey) while planning his wedding to another woman. Mary, who has always been a professional, must now deal with her own feelings and try to decide whether to pursue Steve or to continue with the wedding as planned.

Best The Wedding Planner Movie Quote

I don’t know your dad’s first name, I don’t know if you ever wore braces, or contacts, or glasses and I have no idea how you came to be a wedding planner, Mary. But I do know the curves of your face. And I know every fleck of gold in your eyes. I know that the night at the park was the best time I’ve ever had. ~ Steve Edison

Watch The Wedding Planner: Amazon | YouTube | Google Play


10) How to Lose a Guy in 10 Days

How to Lose a Guy in 10 Days is a 2003 romantic comedy film directed by Donald Petrie and starring Kate Hudson and Matthew McConaughey. The film is about Andie Anderson (Hudson), a writer for a women’s magazine who is assigned to write an article about “How to Lose a Guy in 10 Days.” Meanwhile, advertising executive Benjamin Barry (McConaughey) bets his colleagues that he can make a woman fall in love with him in 10 days. Andie and Benjamin meet and Andie decides to use Benjamin as the subject of her article, while Benjamin is determined to win Andie’s heart.

Best How to Lose a Guy in 10 Days Movie Quote

I miss you Benny boo boo…boo boo boo. ~ Andie

Watch How to Lose a Guy in 10 Days: Amazon | YouTube | Google Play


11) Hope Floats

Hope Floats is a 1998 romantic drama film directed by Forest Whitaker and starring Sandra Bullock, Harry Connick Jr., and Gena Rowlands. The film tells the story of a woman named Birdee (Bullock) who returns to her small hometown with her daughter after her husband publicly reveals that he is having an affair on a talk show. As she struggles to rebuild her life and relationships, she finds herself falling in love with her old friend, Justin (Connick Jr.).

Best Hope Floats Movie Quote

Childhood is what you spend the rest of your life trying to overcome. That’s what momma always says. She says that beginnings are scary, endings are usually sad, but it’s the middle that counts the most. Try to remember that when you find yourself at a new beginning. Just give hope a chance to float up. ~ Birdie Pruitt

Watch Hope Floats: Amazon | YouTube | Google Play


12) Eat Pray Love

Eat Pray Love is a 2010 romantic drama film directed by Ryan Murphy and starring Julia Roberts. The film is based on the memoir of the same name by Elizabeth Gilbert. The film follows Gilbert (Roberts) as she embarks on a journey of self-discovery after a difficult divorce. She travels to Italy, India, and Bali, learning about pleasure, devotion, and balance along the way, and learning to find herself and fall in love again.

Best Eat Pray Love Movie Quote

You don’t need a man, Liz. You need a champion. ~ Felipe

Watch Eat Pray Love: Amazon | YouTube | Google Play


13) Stuck in Love

Stuck in Love is a romantic comedy-drama film released in 2012, directed by Josh Boone and starring Greg Kinnear, Jennifer Connelly, Lily Collins, Logan Lerman, and Kristen Bell. The movie follows the story of a successful novelist, played by Kinnear, and his dysfunctional family, consisting of his ex-wife, played by Connelly, and their two children, a college student and an aspiring writer, played by Collins and Lerman, respectively, and their struggles with love, relationships, and family.

Best Stuck in Love Movie Quote

I could hear my heart beating. I could hear everyone’s heart. I could hear the human noise we sat there making, not one of us moving, not even when the room went dark. ~ Bill Borgens

Watch Stuck in Love: Amazon | YouTube | Google Play


14) The Wedding Date

The Wedding Date is a 2005 romantic comedy film directed by Clare Kilner and starring Debra Messing and Dermot Mulroney. The film is about Kat Ellis (Messing) who hires a male escort named Nick Mercer (Mulroney) to pose as her boyfriend at her sister’s wedding in London. As they spend time together, Kat and Nick begin to develop feelings for each other and must navigate the complexities of their arrangement.

Best The Wedding Date Movie Quote

Close your eyes. Close your eyes. Close… your… eyes. You’re safe. You can relax. I’m not going to kiss you. He’s gonna be so sorry he lost you, so stop worrying. Forget the past. Forget the pain. And remember what an incredible woman you are. You do that and he’ll realize what he lost. ~ Nick Mercer

Watch The Wedding Date: Amazon | YouTube | Google Play


15) Keeping the Faith

Keeping the Faith is a 2000 romantic comedy-drama film directed by Edward Norton, who also stars in the film alongside Ben Stiller and Jenna Elfman. The film is about two childhood friends, Jake Schram (Stiller) and Brian Finn (Norton), who are both priests, and their shared friendship with a woman named Anna Reilly (Elfman). Jake and Brian are forced to confront their feelings for Anna and their faith as they navigate the complexities of their relationships.

Best Keeping the Faith Movie Quote

May those who love us, love us. And those who don’t love us – may God turn their hearts. And if He cannot turn their hearts, may he turn their ankles, so that we may know them by their limping. ~ Indian Bartender

Watch Keeping the Faith: Amazon | YouTube | Google Play


16) Shall We Dance?

Shall We Dance? is a 2004 romantic comedy-drama film directed by Peter Chelsom and starring Richard Gere, Susan Sarandon, and Jennifer Lopez. The film is about John Clark (Gere), a successful lawyer, who begins taking ballroom dance lessons after feeling unfulfilled in his life. As he becomes more involved in the dance community, he begins to discover new passions, and he finds himself falling for his dance instructor, Paulina (Lopez).

Best Shall We Dance? Movie Quote

We need a witness to our lives. There are a billion people on the planet… I mean, what does any one life really mean? But in a marriage, you’re promising to care about everything. The good things, the bad things, the terrible things, the mundane things… all of it, all of the time, every day. You’re saying ‘Your life will not go unnoticed because I will notice it. Your life will not go un-witnessed because I will be your witness’. ~ Beverly Clark

Watch Shall We Dance?: Amazon | YouTube | Google Play


17) Notting Hill

Notting Hill is a 1999 romantic comedy film directed by Roger Michell and starring Julia Roberts and Hugh Grant. The film is about William Thacker (Grant), a bookstore owner, who falls in love with a famous actress named Anna Scott (Roberts) after she walks into his bookstore. Despite the obstacles they face as a result of their vastly different lifestyles, William and Anna’s love for each other grows stronger.

Best Notting Hill Movie Quote

I’m also just a girl, standing in front of a boy, asking him to love her. ~ Anna Scott

Watch Notting Hill: Amazon | YouTube | Google Play


18) Something’s Gotta Give

Something’s Gotta Give is a 2003 romantic comedy film directed by Nancy Meyers and starring Jack Nicholson and Diane Keaton. The film is about Harry Sanborn (Nicholson), a successful music producer and confirmed bachelor, who begins dating a woman named Marin (Amanda Peet) who is half his age. When Harry suffers a heart attack while visiting Marin’s mother, Erica (Keaton), he ends up spending more time at her beach house, and he begins to develop feelings for her.

Best Something’s Gotta Give Movie Quote

I don’t want my bearings. I’ve had my bearings my whole goddamn life. I feel something with you I never really knew existed. Do you know what that’s like, after a 20-year marriage to feel something for another person that is so…? That… Oh, Right. Right. Not your problem. God. Do you know that I’ve written this, but I never really got it? Do you know what this is? This is heartbroken. ~ Erica Barry

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19) Two Weeks Notice

Two Weeks Notice is a romantic comedy film released in 2002, directed by Marc Lawrence and starring Sandra Bullock and Hugh Grant. The film follows the story of a successful lawyer, played by Bullock, who falls in love with her boss, played by Grant, after working for him for two years. However, when she decides to quit her job, she gives her boss two weeks notice, and during this time, they both realize that they have feelings for each other.

Best Two Weeks Notice Movie Quote

Before you came into my life I could make all kinds of decisions, now I can’t, I’m addicted, I have to know what you think! ~ George Wade

Watch Two Weeks Notice: Amazon | YouTube | Google Play


20) The Mirror Has Two Faces

The Mirror Has Two Faces is a romantic comedy-drama film released in 1996, directed by and starring Barbra Streisand. The movie follows the story of a shy and plain woman, played by Streisand, who is a college professor of literature and falls in love with a handsome and charming colleague, played by Jeff Bridges. They decide to get married but with a non-physical agreement and this leads to complications in their relationship.

Best The Mirror Has Two Faces Movie Quote

I tell you what I envy about people in love – I’d love it if someone knew me, I mean really knew me. What I like, what I’m afraid of, what kind of toothpaste I use. ~ Rose Morgan

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21) My Best Friend’s Wedding

My Best Friend’s Wedding is a romantic comedy film released in 1997, directed by P.J. Hogan and starring Julia Roberts, Dermot Mulroney, Cameron Diaz, and Rupert Everett. The movie follows the story of a woman, played by Roberts, who realizes she is in love with her long-time best friend, played by Mulroney, just as he is about to marry another woman, played by Diaz.

Best My best Friend’s Wedding Movie Quote

Lower. The pus that infects the mucous… that cruds up the fungus… that feeds on the pond scum. On the other hand, thank you… for loving me that much. That way, it’s – it’s pretty flattering. ~ Michael O’Neill

Watch My Best Friend’s Wedding: Amazon | YouTube | Google Play


22) Runaway Bride

The Runaway Bride is a romantic comedy film released in 1999, directed by Garry Marshall and starring Julia Roberts and Richard Gere. The movie follows the story of a woman, played by Roberts, who has a habit of leaving men at the altar, and a journalist, played by Gere, who is assigned to write a story about her. As they spend time together, they begin to fall in love.

Best Runaway Bride Movie Quote

Look, I guarantee there’ll be tough times. I guarantee that at some point, one or both of us is gonna want to get out of this thing. But I also guarantee that if I don’t ask you to be mine, I’ll regret it for the rest of my life, because I know, in my heart, you’re the only one for me. ~ Ike Graham

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23) Under the Tuscan Sun

Under the Tuscan Sun is a romantic comedy-drama film released in 2003, directed by Audrey Wells and starring Diane Lane, Sandra Oh, and Raoul Bova. The movie follows the story of a recent divorcee, played by Lane, who decides to take a trip to Tuscany, Italy, and impulsively buys a villa there. She soon begins to build a new life for herself with the help of the locals and finds herself falling in love with a charming Italian man, played by Bova.

Best Under the Tuscan Sun Movie Quote

Do you know the most surprising thing about divorce? It doesn’t actually kill you. Like a bullet to the heart or a head-on car wreck. It should. When someone you’ve promised to cherish till death do you part says “I never loved you,” it should kill you instantly. You shouldn’t have to wake up day after day after that, trying to understand how in the world you didn’t know. The light just never went on, you know. I must have known, of course, but I was too scared to see the truth. Then fear just makes you so stupid. ~ Frances

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24) A Good Year

A Good Year is a romantic comedy-drama film released in 2006, directed by Ridley Scott and starring Russell Crowe, Marion Cotillard, and Albert Finney. The movie follows the story of a London-based financier, played by Crowe, who inherits a vineyard in Provence, France from his uncle, played by Finney, and decides to move there to start a new life. He reconnects with an old childhood friend, played by Cotillard, and starts to fall in love with her.

Best A Good Year Movie Quote

I would like a lifetime spent with an irrational and suspicious goddess, some short-tempered jealousy on the side, and a bottle of wine that tastes like you, a glass that’s never empty. ~ Max Skinner

Watch A Good Year: Amazon | YouTube | Google Play


25) It’s Complicated

It’s Complicated is a romantic comedy film released in 2009, directed by Nancy Meyers and starring Meryl Streep, Alec Baldwin, and Steve Martin. The movie follows the story of a divorced woman, played by Streep, who reconnects with her ex-husband, played by Baldwin when they both attend their son’s college graduation, and they end up having an affair while both are in relationships with other people.

Best It’s Complicated Movie Quote

Do you spoke smot? ~ Jane Adler

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26) My Big Fat Greek Wedding

My Big Fat Greek Wedding is a romantic comedy film released in 2002, written by and starring Nia Vardalos. The film follows the story of Toula Portokalos, a Greek-American woman who falls in love with a non-Greek man, and the cultural differences and family dynamics that come with their relationship.

Best My Big Fat Greek Wedding Movie Quote

My dad believed in two things: That Greeks should educate non Greeks about being Greek and every ailment from psoriasis to poison ivy can be cured with Windex. ~ Toula Portokalos

Watch My Big Fat Greek Wedding: Amazon | YouTube | Google Play


27) As Good As It Gets

As Good as It Gets is a romantic comedy-drama film released in 1997, directed by James L. Brooks and starring Jack Nicholson, Helen Hunt, and Greg Kinnear. The movie follows the story of a misanthropic, obsessive-compulsive novelist, played by Nicholson, who forms an unlikely friendship with a single mother, played by Hunt, and her son, played by Kinnear.

Best As Good As It Gets Movie Quote

You make me want to be a better man. ~ Melvin Udall

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These 27 feel-good rom-coms are sure to keep you cozy and entertained this winter. From classic favorites to new releases, these films are guaranteed to put a smile on your face and warm your heart. Whether you’re snuggled up on the couch with a loved one or enjoying a solo movie night, these romantic comedies are the perfect way to beat the winter blues. So grab your popcorn, curl up under a blanket, and enjoy the magic of love and laughter this winter season.

Juli Becker
Juli Beckerhttps://possibilitypress.org
I believe information can change lives. That’s why I’ve established Possibility Press as a beacon for those who are seeking inspiration. Let’s embark on a journey into the realm of possibilities together! Welcome to the Possibility Press community!

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