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Give Yourself The Gift Of Watching These Classic Rom-Coms This Valentine’s Day


Picking a movie is always a daunting task in my family. My mom and I have had to sit through our fair share of war movies with no discernible plot, while my dad and brother have patiently suffered through “Gone With The Wind.” The beauty of a good rom-com is having enough “rom” to satisfy more sentimental audiences and enough “com” to keep less romantic viewers interested.

As a connoisseur of the “rom,” I can’t guarantee all the movies on this list will please the most macho of audiences, but I can promise they’re quality classics everyone should see at least once.

Father Of The Bride

There is nothing like watching Steve Martin and a hilariously flamboyant Martin Short argue about a front yard full of swans. In this 1991 classic (a remake of the 1950 Elizabeth Taylor movie), Martin plays a practical but loving father who has a hard time coming to terms with his daughter’s marriage—and the fact that he has to pay for it. Short plays the wedding planner brilliantly with an indeterminate but comical accent.

The comedy in this movie—and in its 1995 sequel—is superb. But the film is also a heartwarming reminder of the gifts of family and memory. Especially in a year when pandemic restrictions have forced many to downsize their weddings and other celebrations, “Father of the Bride” reminds us that everyday moments with loved ones are more important than a picture-perfect ceremony. I never watch it without tearing up at the end, and I never watch it without belly laughing.


This 2005 classic stars Will Smith as a “date doctor,” who helps men learn to pursue women intentionally and creatively. He successfully pairs wealthy, beautiful celebrity Allegra Cole with his kindhearted but stereotypically average client Albert. In his own romantic pursuits, however, he finds his tactics less successful.

Albert and Allegra’s relationship is adorable and heartwarming, but the movie also brings a profound message to an audience steeped in hookup culture.

The art of dating is neither a means to an inevitable one-night stand nor a drab ritual of “hanging out.” Dating shouldn’t be a passive excursion—as Hitch shows us, dating is an opportunity to be authentic but also to put thought and effort into making another person feel interesting.

High Society

This musical rom-com is definitely on the effervescent side, but a cast that includes Frank Sinatra, Bing Crosby, Louis Armstrong, and Grace Kelly makes up for any deep intrigue the film might lack. Kelly plays Tracy Lord, a spoiled heiress and the divorced wife of jazz musician C. K. Dexter Haven (played by Crosby), who happens to live next door.

While Lord prepares to marry another man, her ex-husband tries to win her attention, as does a journalist sent to cover the wedding, played by Sinatra. Armstrong and his band grace the whole drama with toe-tapping musical numbers.

Fun fact: this was Kelly’s last film before she left Hollywood to marry real-life Prince Rainier of Monaco, so the whopping 10-carat ring she wears in the movie is her real engagement ring.

The film is a remake of the 1940 movie “The Philadelphia Story,” which has no less impressive of a cast, featuring Katherine Hepburn, James Stewart, and Cary Grant.

Miss Congeniality

Grace Hart (Sandra Bullock) is a tough FBI agent—not exactly the girly type. When there’s a potential bomb threat at a national beauty pageant, Hart has to go undercover as a contestant, where she struggles to fit in with the ballgowns and bouffants.

You may not come away from “Miss Congeniality” with a deep understanding of how to achieve world peace, but it’s nonetheless fun and lighthearted slapstick comedy.


If, like me, you think Breakfast at Tiffany’s is wildly overrated, try this Audrey Hepburn classic instead. The movie begins at an alpine ski lodge, where soon-to-be widow Regina Lampert (Hepburn) meets a mysterious stranger (played by Cary Grant). The rest of the movie is as intriguing and delightful as its opening.

Regina returns from vacation to find her apartment completely empty and her husband murdered. At his funeral, she meets three men who fought with her husband in World War II and are now after money he stole. Lampert seeks help from Grant’s character, while also wondering if he’s actually the one behind the murder.

You’ve Got Mail

I will admit I don’t exactly get why Tom Hanks is cast in so many rom-coms. But with Meg Ryan, a killer soundtrack, and the most charming bookstore aesthetic, this 1998 film is an enduring classic.

Ryan plays the owner of family bookstore The Shop Around The Corner, which is threatened when giant corporation Fox Books moves in across the street. Ryan and Hanks, the owner of Fox Books, antagonize each other every time they meet. But when they’ve both struck up a conversation with an unnamed stranger in an internet chat room, they just happen to be chatting with each other.

While You Were Sleeping

Yes, Sandra Bullock makes the list twice. In another classic with less shtick but more good schmaltz than “Miss Congeniality,” this 1995 hit follows Chicago metro employee Lucy after she rescues a handsome stranger from falling onto the rails. They’ve never officially met, but she’s watched him from afar on his commute and fantasizes about a romance with him.

After the accident puts him in the hospital with a coma, a nurse overhears Lucy lament “I was going to marry him!” Assuming she’s the fiancée, the nurse introduces Lucy to the rest of the family, who welcomes her before she has a chance to correct them.

Whether you’re cozied up with your sweetheart or enjoying a girls’ night, grab some popcorn (and chocolate) and treat yourself to one of these seven classics this Valentine’s Day.