10 Great Rom-Coms To Watch If You Love My Best Friend’s Wedding

1997’s My Best Friend’s Wedding featured Julia Roberts as food critic Julianne Potter trying to prevent/ruin the wedding that is set to occur between her best friend Michael (Dermot Mulroney) and another woman. Realizing that she loves Michael and can’t stand his soon-to-be-wife, Kimmy (Cameron Diaz), Julianne embarks on a scheme that inflicts absolute disaster, nearly accomplishing the break-up she was aiming for.

When Julianne finally realizes Michael truly loves Kimmy, she lets him go and accepts his marriage, even managing to conjure up some happiness for the new couple. It’s a great rom-com, despite the fact that it doesn’t exactly give the typical happy ending we’ve all come to expect from the genre. Here are 10 other rom-coms that are worth watching, especially if you love this one.

10 Pretty Woman

Another Julia Roberts rom-com, this 1990 film launched Roberts to super-stardom overnight. Roberts plays sex worker Vivian who falls for Edward (Richard Gere), a wealthy businessman that’s hired Vivian for a week to accompany him to events.

The two are reluctant to make their arrangement anything more than a business deal, but come to truly care for one another, leading to Edward climbing up Vivian’s fire escape and declaring his love for her, just as she always dreamed. If that’s not a formula for a heartwarming rom-com, we don’t know what is.

9 The Wedding Singer

Drew Barrymore and Adam Sandler star in this 1980s flashback rom-com. Sandler is musician Robbie Hart, who is left at the altar by his bride-to-be. Heartbroken, he refuses to sing at any more weddings. Meanwhile, Julia (Barrymore) finally gets her fiancé Glenn to set a date for their wedding. As she’s new to town, she enlists Robbie’s help to pick out a wedding cake, a band, etc.

While the two spend more and more time together, they begin to fall for each other but experience some setbacks. It all leads up to Julia nearly eloping with Glenn, only for Robbie to end up on the same plane and sing a beautiful song to win her back, with none other than Billy Idol on-board.

8 The Wedding Date

This 2004 comedy starred Debra Messing and Dermot Mulroney. Mulroney plays Nick, whom Kat (Messing) hires to accompany her to her sister’s wedding in England in order to impress her ex, who dumped her unexpectedly a few years before. Nick soon has everyone, even Kat, believing that he and Kat are hopelessly and passionately in love.

Then, Kat begins learning some disturbing truths from her past involving her ex and her sister that shatters her world, which briefly causes Nick to leave. Luckily, Nick returns, and Kat realizes that he is the one for her, and vice versa.

7 50 First Dates

Adam Sandler and Drew Barrymore return in their second rom-com together, this time in a Hawaiian setting. Lucy (Barrymore) is an artist that suffered head trauma in a car crash, causing her to be unable to retain new memories. Henry (Sandler) is a womanizer that stops cold turkey upon meeting Lucy, whom he comes to find is the woman of his dreams.

Trouble is, he has to find a way to get Lucy to fall in love with him every day, as she’ll never be able to remember him because of her condition. Henry hilariously tries and fails to get Lucy to fall for him on a daily basis, but finds that working hard for love helps him achieve his greatest happiness.

6 A Lot Like Love

This rom-com skips through different points in time to portray a chance meeting, followed by multiple encounters between Oliver (Ashton Kutcher) and Emily (Amanda Peet). It seems that at each point in time one is happy and settled and the other is not, but the two each work through their ups and downs and seem to find each other when they need it most.

It’s intricately connected in one finding the other at pivotal times in their life and being there as a support system. Eventually, the two end up where they need to be: together.

5 Made of Honor

Best friends Tom and Hannah are inseparable. They have an easy rapport, a great chemistry, and are clearly perfect for each other. It’s obvious that Hannah has feelings for Tom, but doesn’t pursue because she believes Tom doesn’t see her in that way. The thing is, Tom does care for Hannah, but fails to realize it until after she’s met and become engaged to someone else while on a work trip overseas in Scotland.

Hannah appoints Tom her maid of honor, and Tom sets out to win Hannah back while helping her plan her wedding to another man. It’s zany, it’s fun, and it’s scenic, considering the film takes us from New York City to Scotland. Patrick Dempsey and Michelle Monaghan play their characters to perfection in this 2008 rom-com.

4 Definitely, Maybe

Ryan Reynolds stars as Will, a man that is going through a divorce who ends up telling his daughter Maya (Abigail Breslin) the story of how he met her mother. The thing is, he changes names and facts so as to get Maya to guess who her mother is in the story.

As Will delves further into the tale, telling his daughter about the three women in his life that he was the most seriously involved with, he finds that reexamining the past can help him piece together his future (with Maya’s help, of course).

3 P.S. I Love You

Gerard Butler and Hilary Swank star in this heartwarming, yet heartbreaking rom-com. Gerry (Butler) and Holly (Swank) are a happily married couple making their way through life when Gerry dies of a brain tumor, leaving Holly to make sense of it all. She grieves, flashing back throughout the film to her first meeting with Gerry, their insignificant fights, and other special moments between them.

Gerry has written a series of letters for Holly to read upon his death, hoping to help her through the grieving process and get her back to living life again. It’s the most beautiful love story that comes to a tragic end, but it’s the kind of love that lasts forever–which also helps Holly to be able to move on.

2 While You Were Sleeping

Lucy (Sandra Bullock) harbors a massive crush on one of the commuters that frequents the train station where she works. When muggers push the man onto the tracks, Lucy saves his life and follows him to the hospital, where he falls into a coma. Thanks to a misunderstanding, Lucy suddenly finds herself in a fake engagement to Peter (the comatose man) and surrounded by Peter’s sweet but somewhat overbearing family.

The lonely Lucy is too caught up in the panic and too attached to her new family to tell the truth, but she’s simultaneously falling for Peter’s brother Jack (Bill Pullman) while the lie continues getting out of control. Of course, the truth must be revealed, but things turn out wonderfully for Lucy despite some fallout. This film also takes place around the holiday season, so this would be a perfect rom-com to add to your list this time of year.

1 The Holiday

Another Christmastime rom-com, this one finds complete strangers Cameron Diaz and Kate Winslet switching homes for the holidays and bettering their lives because of it. Iris (Winslet) leaves snowy England for sunny Los Angeles, hoping to move on from a man she loved that she’s recently learned has gotten engaged. Amanda (Diaz) is hoping for the same after a nasty break-up.

Each woman finds love in their new towns, as well as a renewed sense of purpose as Amanda finds a family and Iris forgives and allows herself to move on. Touching and of course, featuring a happy ending, this film tops the list because it’s the perfect rom-com for any season (especially the holidays).

About The Author

Kacie Lillejord
(374 Articles Published)

A Seattle native, Kacie has loved entertainment in the forms of books, films, television and music since day one. Inspired by a filmmaker relative, Kacie has been pursuing a career in the film and television industry in Los Angeles ever since. A graduate of The University of Arizona, Kacie has written for her college newspaper The Daily Wildcat, Harness Magazine, 25YL, and now has added Screen Rant to her resume. She loves writing and all things pop culture.

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