As the weather gets colder, sometimes all we want to do is crawl under a few blankets and watch a movie. What better way to get into the warm and cozy mood than with a lighthearted, funny film with lovable characters who you just know will have a happy ending?
1. How to Lose a Guy in 10 Days
Released: 2003
Starring: Kate Hudson, Matthew McConaughey
What it’s about: Andie Anderson (Hudson) is Composure magazine’s primary how-to girl. When her friend is dumped after less than two weeks of dating a guy, Andie is inspired to write a reverse how-to article: How to Lose a Guy in 10 Days, in which she enters a relationship and tries to push the man away. Ben Barry (McConaughey) is an advertiser who wants to move up in his company and advertise diamonds instead of sports products. His two female rival co-workers think that as a man he doesn’t understand the romance that comes with diamonds, so they challenge him to make a woman fall in love with him in 10 days. So, what happens when Ben becomes Andie’s experiment and Andie becomes Ben’s?
Why you should watch it: When Matthew McConaughey was nominated for and won an Oscar, a term came to be known as the McConaissance, a modern-day Renaissance in which a man known for making primarily romantic comedies transformed into a distinguished actor overnight. There’s a reason people associate him with rom-coms – he’s the king. Not only is Ben Barry one of the most charming and genuine men you will ever see, but McConaughey’s chemistry with Hudson is unmatched. The story is a unique and unusual take on a rom-com that will leave you laughing and more in love than ever. I would say this is one of the greatest rom-coms of all time.
2. The Proposal
Released: 2009
Starring: Sandra Bullock, Ryan Reynolds
What it’s about: Margaret Tate (Bullock) is the executive editor-in-chief of a publishing company in New York, and Andrew Paxton (Reynolds) is her assistant who wants to be an editor. Margaret is the monster of the office and Andrew is the only one who can handle her. When Margaret’s work visa expires and she is about to be deported back to Canada, she makes a deal with Andrew: marry her so she can stay in the country and he will become editor and can publish a book he’s had his eye on. In order to keep up the charade, Margaret goes to Andrew’s hometown, Sitka, Alaska and meets all his family and old friends. What happens when Margaret, who has been an orphan since she was 16, is surrounded by the love of a family?
Why you should watch it: It’s hilarious and endearing. The ensemble cast will guarantee that you have a large group of characters to fall in love with. Bullock and Reynolds work well together and make you want dozens of sequels to the film. Best of all, this film has a lot of memorable scenes that will always stay with you, whether they are as funny as Margaret breaking it down in the woods, or as heartbreaking as Andrew hollowing out an old canoe every time he has an argument with his father.
3. The Holiday
Released: 2006
Starring: Cameron Diaz, Kate Winslet, Jude Law, Jack Black
What it’s about: Iris Simpkins (Winslet) is a column writer who lives in a small cottage in Surrey, England. Amanda Knox (Diaz) is a rich Los Angeles company owner who produces movie trailers. Upon finding disappointment and heartbreak in love, they find each other on a home-swapping website and agree to switch places for two weeks. Iris loves the glamour of living in a L.A. home while Amanda finds the country life boring. She plans to go home, until she meets Iris’s brother Graham (Law). Meanwhile, Iris meets one of Amanda’s friends, Miles (Black) back in L.A. Will these newfound additions to their lives keep them in their holiday homes, or will they want to go back home?
Why you should watch it: Even though it probably isn’t, it feels like “The Holiday” is a ridiculously underrated film. It feels like one of those ensemble rom-coms a la Love, Actually but with a much smaller cast. Having four huge stars together onscreen keeps the story easy to follow and allows for deeper character development. Best of all, this movie is all about escape! What better place for you to escape your life for a few hours than by taking a double vacation with the characters? It’s sure to satisfy every viewer’s vacation desires, whether it be a trip to sunny Los Angeles, or quaint England.
4. Fever Pitch
Released: 2005
Starring: Jimmy Fallon, Drew Barrymore
What it’s about: Ben Wrightman (Fallon) has one true love in his life: the Boston Red Sox. Ever since he was a little seven-year-old boy and his uncle took him to his first Sox game, he has been hooked. He has season tickets, is never seen without some Red Sox merchandise on his person, and his apartment looks like the MLB Pro Shop exploded in it. Ben is basically a seven-year-old trapped in Jimmy Fallon’s body. One day, he meets Lindsay Meeks (Barrymore) who is his complete opposite. She is an executive who works too much and is too much of an adult. Ben is able to merge Lindsay into Red Sox Nation, his world. But what happens when Lindsay isn’t able to bring out the adult side of Ben?
Why you should watch it: First of all, it’s about the Red Sox. Is there any better rom-com to watch in Boston than one where one of the main characters is the city’s most beloved sports team? Fallon and Barrymore are two of the most adorable people on the planet and they make sure the film is nothing but fun. You get to watch two people develop a friendship while also developing a relationship. Plus, this movie is so different from the typical rom-com. It’s about the Red Sox, for goodness sake!
5. The Wedding Planner
Released: 2001
Starring: Jennifer Lopez, Matthew McConaughey
What it’s about: Mary Fiore (Lopez) is a wedding planner for a top company. One day, she meets Dr. Steven James ‘Eddie’ Edison (McConaughey) when he saves her life, then treats her at his hospital. They go on a romantic date only for him to show up the next day with his fiancée, Fran. They are Mary’s new clients! Meanwhile, Mary’s father is trying to set her up with a childhood friend, Massimo, who has a heart of gold but isn’t exactly prince charming. What happens when the characters have to choose between being with who they love and marrying out of obligation?
Why you should watch: We started with Matthew McConaughey and we have to end with Matthew McConaughey! What is more of a rom-com than an early 2000s one starring Matthew and J-Lo? This film has everything that makes a typical rom-com: the man and woman meet each other in a spontaneous and romantic way, have a few bumps in the road, and end up together. If you want to watch something simple and sweet, choose this.
If you don’t have time to marathon five romantic comedies, choose your favorite one and enjoy a night in. If you don’t have time for even one, the Family Guy episode “Valentine’s Day in Quahog” puts every rom-com stereotype and trope into a 22-minute episode. So, that’s also an option!