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Like modern offerings, most classic rom-com movies also explore different romance tropes. When it comes to the fake dating angle, romance fans particularly enjoyed How to Lose a Guy in 10 Days by Donald Petrie. In this classic rom-com movie, Kate Hudson and Matthew McConaughey play Andie and Benjamin respectively, who agree to date one another due to certain ulterior motives.
Even though neither of them is in it for the long haul, they realize that they are extremely compatible as they spend more and more time together. How to Lose a Guy in 10 Days wins viewers over with its likable characters, witty dialogue, and light-hearted narrative. Although this classic rom-com gets a lot right, the main highlight has to be the sizzling chemistry between Hudson and McConaughey.
Cinephiles who enjoyed How to Lose a Guy in 10 Days and are looking for similar classic rom-com movies should check out the popular titles on this list.
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Disclaimer: This list contains information from various sources and contains the author's opinion.
She's All That, The Proposal, and five other classic rom-com movies that are as romantic as they are funny
1) Picture Perfect (1997)
Friends fans wouldn't want to miss out on this classic rom-com movie by Glenn Gordon Caron as it stars Jennifer Aniston in the lead. Aniston plays Kate Mosley, a struggling advertising executive who has a hard time getting promoted because her boss doesn't see her as responsible and stable. In order to get in his good books, she pretends to be engaged to a man she barely knows.
Like How to Lose a Guy in 10 Days, this classic rom-com movie showcases how easily pretend romance can escalate to real feelings. Aniston has great chemistry with Jay Mohr, Kate's fake fiance. Picture Perfect is a light-hearted classic rom-com movie that is easy to watch and yet has its fair share of sincere moments that will appeal to romance fans.
Where to watch: This Jennifer Aniston starrer is available on Disney+ and Prime Video.
2) Never Been Kissed (1999)
Drew Barrymore has appeared in several classic rom-com movies over the years and Never Been Kissed by Raja Gosnell, in particular, is considered a cult classic. Barrymore's character, Josie Geller, has a lot in common with Kate Hudson's Andie in How to Lose a Guy in 10 Days as they are both in pursuit of a sensational story.
When Josie goes undercover at a high school for her scoop, she quickly feels out of place but she soon learns to make fond memories that will last a lifetime. She also falls for the charming English teacher portrayed by Michael Vartan.
While the narrative is entertaining, the true star of the movie has to be Barrymore. The way she brings the character's vulnerabilities to the surface without making her seem like a weak character certainly deserves credit.
Where to watch: Never Been Kissed can be streamed on Apple TV+, Prime Video, and Disney+.
3) She's All That (1999)
This movie by Robert Iscove will particularly appeal to those who enjoy coming-of-age narratives. In the lead are Freddie Prinze Jr. and Rachael Leigh Cook who play Zack Siler and Laney Boggs.
Like Benjamin in How to Lose a Guy in 10 Days, Zack also makes a bet with his buddies that prompts him to get close to the serious but good-hearted Laney. All he has to do is give her a makeover that helps her become the next prom queen. However, during the process, they both start to develop feelings for one another which leads to several complications.
This feel-good classic rom-com movie does suffer from the usual genre clichés but it still finds a way to keep the viewers entertained from start to finish. The way the leads build their connection over small yet significant moments helps encourage the viewer to root for them.
Where to watch: This delightful classic rom-com movie is available for streaming on Prime Video.
4) Two Weeks Notice (2002)
Seeing how Hugh Grant made a name for himself playing charming romantic leads, it is only natural to have one classic rom-com movie on this list with him in it. In this Marc Lawrence rom-com, Grant stars alongside Sandra Bullock. Grant plays George, a narcissistic real estate developer while Bullock plays a level-headed, competent liberal lawyer who works for him.
When she becomes sick of his self-serving ways, she files her resignation, leaving George stumped. As he is unwilling to let her go, he creates problems when she applies for other jobs. Even though they clash every time they meet, it becomes obvious that beneath the anger and frustration lie hints of something more.
Like How to Lose a Guy in 10 Days, the banter in this classic rom-com movie is top-notch. The pace of the story progression, the character development arcs and the perfectly-timed humor, everything combine to create a fun movie-watching experience.
Where to watch: This classic rom-com movie starring Hugh Grant is available on Netflix, Apple TV+, and Prime Video.
5) The Wedding Date (2005)
This classic rom-com movie by Clare Kilner, similar to How to Lose a Guy in 10 Days, dabbles in the famous fake dating trope. Debra Messing plays Kat Ellis who is desperate to get a date for her sister's wedding in order to get back at her ex. She pays Dermot Mulroney's character, Nick Mercer, a charismatic male escort to pretend to be her boyfriend.
The palpable chemistry between Messing and Mulroney really helps the audience feel invested in their relationship which evolves as the narrative moves forward. Even though there are many silly and fun moments in this classic rom-com movie, it also touches upon meaningful subjects such as the importance of self-worth and self-love.
Where to watch: The Wedding Date can be viewed on Apple TV+ and Prime Video.
6) Failure to Launch (2006)
Matthew McConaughey, the leading man of How to Lose a Guy in 10 Days, also plays a central character in this classic rom-com movie by Tom Dey. He plays Tripp, an easy-going 35-year-old who is still living with his parents. When his parents are unsuccessful in making him leave on their own, they bring in an expert, Paula, portrayed by Sarah Jessica Parker.
Like a lot of rom-coms, the narrative can feel a little predictable at times but the movie still has enough captivating characters, funny lines and engaging scenes that will keep fans of the genre happy. McConaughey, as always, has an easy charm that is complemented by Parker's effortless elegance and alluring demeanor.
Where to watch: This Sarah Jessica Parker starrer is available for streaming on Netflix, Prime Video, and Apple TV+.
7) The Proposal (2009)
This is the second classic rom-com movie on this list to star Sandra Bullock. She plays Margaret Tate, a Canadian editor-in-chief working in New York City. When her visa renewal application is denied, she panics. She then convinces her overworked personal assistant, Andrew Paxton, portrayed by Ryan Reynolds, to marry her so that she can get a green card.
Like the main couple in How to Lose a Guy in 10 Days, Margaret and Andrew also start to see each other in a different light when they have to face unexpected ordeals once they decide to go ahead with the sham wedding.
Reynolds' comedic timing is excellent as usual, albeit more muted than when he is in his Deadpool costume. The talented Sandra Bullock is equally charming. Whenever they appear together, it is a treat to listen to their witty banter.
Where to watch: This classic rom-com movie by Anne Fletcher can be streamed on Prime Video and Apple TV+.
These classic rom-com movies belong on every cinephile's watchlist because they offer the best of heartwarming storylines and endearing performances.
