Here are the best rom-coms to watch if you enjoyed Jennifer Lopez and Matthew McConaughey’s The Wedding Planner.
Many great (and often cheesy) romantic comedies starring some of the most well-known actors and actresses of this generation were released in the early-to-mid 2000s. The actors had to deal with heartbreak, job advancements, and botched marriage proposals on a regular basis when they were fresh-faced young stars on the silver screen. Since 2001, Adam Shankman has released The Wedding Planner, starring Jennifer Lopez with Matthew McConaughey and Bridgette Wilson-Sampras.
There is no way to overstate how great this film is, but if you’ve seen it too many times, you might enjoy these other films from the same decade or with a similar storyline that will make you swoon.
10. What Women Want (2000) – Amazon Prime Video
Nancy Meyers, the director of such films as The Holiday, Something’s Gotta Give, and It’s Complicated, directed What Women Want, which came out in 2000. It’s Mel Gibson as Nick Marshall, a conceited ad executive who thinks he knows what women want.
A freak accident grants him the ability to hear what women are thinking while he is experimenting with office women’s products. As a result, when Darcy Macguire (Helen Hunt) joins the team and takes the position he wanted, he immediately puts his new skills to use. Whether or not he makes good use of this ability is up to him. Does he use it to win over the attractive coworker? Men don’t know what women are thinking, as evidenced by the hilarious inside look provided by What Women Want.
9. The Wedding Date (2005) – HBO Max
It was released in 2005 and features Dermot Mulroney, Debra Messing, and Amy Adams as the couple planning their nuptials to each other. As Kat Ellis, a divorced woman planning to attend her sister’s wedding in London, Messing wants to make sure she’s ready to face her ex-fiancé. During the ceremony, she uses a male escort named Nick Mercer (Mulroney) to pretend to be her boyfriend and show that she is truly happy in love.
Unfortunately for Ellis (and the audience), her plan doesn’t pan out the way she had hoped. The film, which is based on Elizabeth Young’s 2002 novel Asking for Trouble, is an exhilarating ride that could end with Ellis meeting her next true love.
8. Just Married (2003) – Amazon Prime, Hulu
Ashton Kutcher and Sarah (Jennifer Aniston) are newlyweds in the romantic comedy Just Married (Brittany Murphy). In Europe, they decide to take a honeymoon, where their love will be put to the test in a variety of ways.
Tom has no money and Sarah comes from a well-to-do family, making the situation even more precarious. They realize they’re in over their heads when Peter Prentiss (Christian Kane), a former suitor, comes after them to persuade Sarah to return home.
7. 27 Dresses (2008) – HBO Max
The epitome of “always a bridesmaid, never a bride” is Katherine (Katherine Heigl), who has been one 27 times. She’ll never say no to her friends again, which is how she ends up in all of these sticky situations. Kevin (James Marsden) is a journalist who broadens her horizons while also serving a greater purpose.
In the midst of everything that happens when Jane’s boss George falls in love with her younger and more impulsive sister Tess (Malin Akerman), she slowly falls for Kevin, a cynical lover.
6. Because I Said So (2007) – Amazon Prime Video
I Said So is a 2007 love story about a controlling mother who plans her daughter’s entire life. A single mother who raised her three daughters, Milly (Mandy Moore), Maggie (Lauren Graham), and Mae (Piper Perabo) alone, plays Daphne Wilder in the film starring Diane Keaton.
Daphne is concerned that Milly will never find the man of her dreams after Maggie and Mae found their soul mates. As soon as she thinks she’s found him, another match appears in Milly’s life to undo all of Daphne’s hard work in creating the perfect match. Whether or not she lets Milly figure things out for herself is up to her.
5. The Sweetest Thing (2002) – Amazon Prime Video
Cameron Diaz, Thomas Jane, Christina Applegate, and Selma Blair star in Roger Kumble’s The Sweetest Thing, a movie about girl power. She plays Christina Walters, a woman who enjoys her single life until she meets Peter Donaghue, the “perfect man” (Jane).
It turns out to be Donaghue’s brother’s wedding when Walters and her best friend Courtney Rockcliffe (Applegate) visit Donaghue at his house to see him at his brother’s wedding. Funny one-liners abound, as does great music, and there’s a heartwarming friendship between the characters in The Sweetest Thing. However, Diaz’s performance in The Sweetest Thing could have been better.
4. My Big Fat Greek Wedding (2002) – HBO Max
In her early 30s, Toula Portokalos (Nia Vardalos) works in the family restaurant as a Greek waitress named Toula (Toula). The couple’s ultimate goal is to marry a nice Greek man, but she wants to enjoy herself first.
She enrolls in a community college to further her education and falls in love with Ian Miller (John Corbett), an English instructor. The only issue is that he isn’t Greek at all! Even as the two begin to date secretly, they are both aware that it will not last.
3. Monster-In-Law (2005) – HBO Max
Charlotte “Charlie” Cantilini (Jennifer Lopez) is a woman who’s had terrible luck in the dating department in the 2005 comedy-romance Monster-In-Law. She meets Kevin Fields (Michael Vartan), a doctor, one day and learns that he comes from a troubled family.
To keep Cantilini at bay, his mother, Viola Fields (Jane Fonda), goes to great lengths. When she learns of her scheme, she scrambles to save her relationship with Mr. Right by any means necessary.
2. My Best Friend’s Wedding (1997) – Netflix
Dermot Mulroney’s character Michael O’Neal (Julia Roberts) calls food critic Julianne “Jules” Porter (Julia Roberts) to announce she is getting married. Years ago, they made a pact that if they weren’t married by the time they turned 28, they would marry each other. Now that time has come for Jules.
While in Chicago for the wedding, Jules realizes she’s been in love with O’Neal all along, and she’s determined to ruin the event after meeting the radiant bride-to-be Kimmy Wallace (Cameron Diaz).
1. How To Lose A Guy In 10 Days (2003) – Peacock
Kate Hudson is the lead actress in the film. In the words of Andie, a Composure lifestyle writer. Because of her best friend’s breakup with a guy, she decides to write an article about getting a man and then losing him for no apparent reason after two weeks of dating. She makes a bet with her boss in order to gain more freedom to write about the topics she enjoys. Benjamin Barry (Matthew McConaughey), an advertising executive, is in a competition with two of his coworkers for a major campaign deal across town. As part of his bargain, he sets out to find Andie and make her fall in love with him.
The bets are harmless at first because Andie and Ben have their sights set on each other, but as time passes, it becomes clear that they are falling for one another. The film, which is based on the same-named children’s book, is a fun choice for a Friday night in the mid-2000s.