27 Amazingly Hilarious Rom-Coms from the 2000s That’ll Lift Your Spirits This Valentine’s: How to Watch Them

27 Amazingly Hilarious Rom-Coms from the 2000s That’ll Lift Your Spirits This Valentine’s: How to Watch Them

Vivian Mwikali
February 01 2023 - 09:44pm

Valentine’s isn’t always romantic for everyone. For some couples, it’s just a usual day because one day of the year doesn’t gratify their love. 

You might be as single as a pringle this month of love, but that doesn't mean that you beat yourself down. This is the perfect opportunity for self-love as you await your next prospect. 

If this sounds familiar, then we've got a Valentine's package for you. It covers forgotten hilarious rom-coms of the 2000s that you can cozy up to any day this month.

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27. ‘Bewitched’ (2005)

A film version of the 1960s sitcom of the same name, starring A-listers Nicole Kidman, Will Ferrell, Shirley MacLaine, Michael Caine, David Alan Grier, Kristin Chenoweth, Jason Schwartzman, Heather Burns, Jim Turner, Stephen Colbert and Steve Carell. 

Buy or rent on Apple TV+ and Prime Video.

26. ‘The Stepford Wives’ (2004)

A remake of the 1975 thriller version, The Stepford Wives stars Nicole Kidman alongside Matthew Broderick, a couple who relocate from New York to Connecticut, Stepford, to reset their family life. They discover sinister occurrences in the manicured environs. 

Bette Midler, Glenn Close, Christopher Walken, Roger Bart, Jon Lovitz, Mike White, David Marshall Grant and Faith Hill, also appear in the film.

Stream on HBO Max and buy/rent on Apple TV+ and Prime Video.

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25. ‘I Hate Valentine’s Day’ (2009)

A sweet Valentine's day rom-com about a love story that sprouted from casual dating. It stars Nia Vardalos and John Corbett, who also co-starred in the beautiful My Big Fat Greek Wedding (2002) and its 2016 sequel. 

Also featuring are Stephen Guarino, Jason Mantzoukas, Rachel Dratch, Mike Starr, Zoe Kazan, Amir Arison, Gary Wilmes and Judah Friedlander. 

Buy/rent on Prime Video or Apple TV+.

24. ‘Ghosts of Girlfriends Past’ (2009)

A celebrity photographer has an epiphany at his young brother's wedding about the tragic future that awaits him if he keeps up his womanizing schemes. 

The film casts Matthew McConaughey, Jennifer Aniston, Breckin Meyer, Lacey Chabert, Michael Douglas, Emma Stone, Daniel Sunjata, Camille Guaty, Robert Forster, Anne Archer, Noureen DeWulf and Rachel Boston. 

Rent/buy on Apple TV+ or Prime Video.

23. ‘Labor Pains’ (2009)

A Lindsay Lohan hidden gem about a broke intern at a publishing company who lies about being pregnant to prevent getting fired. She discovers that having a bun in the oven has its perks, but how long can she keep up the ruse? 

Aside from Lohan, Labor Pains stars Cheryl Hines, Chris Parnell, Luke Kirby, Aaron Yoo, Bridgit Mendler, Willie Garson, Tracee Ellis Ross, Creed Bratton, Janeane Garofalo, Bonnie Somerville, Kevin Covais and Barry Papick. 

Watch for free on Peacock or buy/rent on Prime Video or Apple TV+.

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22. ‘Bride Wars’ (2009)

An underrated rom-com about a long-term sis-friendship that goes murky when two besties, engaged at the same time, start to play dirty on each other, competing for the same wedding venue. 

Bride Wars features an ensemble cast including Anne Hathaway, Kate Hudson, Chris Pratt, Steve Howey, Bryan Greenberg, Candice Bergen, Kristen Johnson, John Pankow, Michael Arden, June Diane Raphael, Casey Wilson, Lauren Bittner, Bruce Altman, Victor Slezak and Kelly Coffield Park. 

Stream via HBO Max or buy/rent on Apple TV + or Prime Video.

21. ‘Chasing Papi’ (2003)

A hilarious Latino romance comedy about three women who find out they are being played by the same guy. Amidst competition for his attention, they realize they are stronger than they perceived. 

Chasing Papi stars the luscious Sofia Vergara, Roselyn Sanchez and Jaci Velasquez alongside Eduardo Verastegui, Lisa Vidal, Diana-Maria Riva, Freddy Rodriguez, Ian Gomez, D.L. Hughley, Linda Mendoza, Maria Conchita Alonso and Joy Enriquez. 

Watch under a subscription on HBO Max or buy/rent on Apple TV+ or Prime Video.

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20. ‘Getting Played’ (2005)

Three single friends make a bet to seduce a targeted random guy to see who wins. Eventually, the played becomes the player as he knew their devious scheme all along. 

The amazing casts include Vivica A. Fox, Carmen Electra, Stacey Dash, Bill Bellamy, Mindy Sterling, Kathy Najimy, Dorian Gregory, Joe Torry, Larry B. Scott, Joseph C. Phillips and Michael Jai White. 

Buy/rent on Prime Video and Apple TV+.

19. ‘Just Married’ (2003)

A dapper Ashton Kutcher and the late Brittany Murphy star as young lovebirds who get married too early. Their honeymoon instantly takes a humorous downside as they uncover that they bit off more than they can chew.  

Besides Kutcher and Murphy, Just Married features David Rasche, David Moscow, Monet Mazur, Valeria Andrews, Christian Kane, Raymond J. Barry, Taran Killam and Thad Luckinbill. 

Rent/buy on Apple TV+ and Prime Video.

18. ‘My Boss’s Daughter' (2003)

A mild-mannered publishing house employee desires his boss's daughter. He agrees to housesit for his boss under the impression that he would get to spend time with his daughter. But one quiet night turns into a comical frenzy filled with misunderstanding and mishaps. 

Ashton Kutcher stars in the lead alongside Tara Reid. There’s also Terence Stamp, Molly Shannon, Jon Abrahams, Jeffrey Tambor, David Koechner, Andy Ritcher, Michael Madsen, Carmen Electra and Kenan Thompson. 

Subscribe at HBO Max to stream or buy/rent on Prime Video or Apple TV+.

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17. ‘License to Wed’ (2007)

The winning romantic comedy features a newly engaged couple, who take a questionable marriage counselling course by a contemptuous priest. The outlandish pre-marital program almost costs them their wedding. 

License to Wed casts John Krasinski, Mandy Moore, Robin Williams, Christine Taylor, Eric Christian Olsen, Josh Flitter, Brian Baumgartner, Mindy Kaling, DeRay Davis, Peter Strauss, Roxanne Hart, Angela Kinsey, Nicole Randall Johnson, Rachel Harris and Grace Zabriskie. 

Buy/rent on Prime Video.

16. ‘Because I Said So’ (2007)

An intrusive mother tries to meddle in her youngest daughter's love life, convinced that she knows what's best. Eventually, the youngest offspring must choose between pleasing her mom and listening to her heart. 

The film's stellar cast includes Diane Keaton, Mandy Moore, Lauren Graham, Piper Perabo, Gabriel Macht, Tom Everett Scott, Stephen Collins, Colin Ferguson, Tony Hale, Zachary Gordon and Ty Panitz. 

Rent/buy on Prime Video or Apple TV+.

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15. ‘Couples Retreat’ (2009)

A delightful rom-com about four couple friends who take a trip to the exotic Hawaii paradise. But what they thought was a relaxation vacation turns out to be an austere couple's therapy program. 

Couples Retreat presents a star-studded cast comprising Vince Vaughn, Malin Akerman, Jason Bateman, Kristen Bell, Jon Favreau, Kristin Davis, Faizon Love, Kali Hawk, Tasha Smith, Jean Reno, Carlos Ponce, Peter Serafinowicz, Ken Jeong, John Michael Higgins and Temuera Morrison. 

Stream the film on Hulu or rent/buy on Prime Video or Apple TV+.

14. ‘Monster-in-Law’ (2005)

A despicable tale of a young woman who must deal with a monstrous future mother-in-law after getting engaged to the love of her life. 

Monster-in-Law casts Jennifer Lopez, Michael Vartan, Jane Fonda, Wanda Sykes, Adam Scott, Monet Mazur, Will Arnett, Elaine Stritch, Stephen Dunham, Annie Parisse, Mark Moses, Randee Heller and Jimmy Jean-Louis. 

Rent or buy on Prime Video and Apple TV+.

13. ‘Along Came Polly’ (2004)

A laugh-stirring romantic comedy about a neurotic actuary who finds love with an ex-classmate when his new marriage falls apart after his bride cheats on him on their honeymoon. 

We have the primary casts Ben Stiller, Debra Messing, Philip Seymour Hoffman, Jennifer Aniston, Hank Azaria, Bryan Brown, Alec Baldwin, Jsu Garcia, Michele Lee and Bob Fischer. 

Stream on Netflix or buy/rent on Apple TV+ or Prime Video.

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12. ‘The Perfect Man’ (2005)

A peculiar rom-com about a single mom who relocates with her two daughters to a new destination every time she gets her heart broken. Her teenage daughter creates an online dating profile using her friend's uncle's details to get her mom interested. The catfishing goes better than anticipated as the mom falls for the lie. 

Starring in The Perfect Man is Hilary Duff, Heather Locklear, Aria Wallace, Chris Noth, Mike O'Malley, Ben Feldman, Caroline Rhea, Kym Whitley, Dennis DeYoung, Mazin Elsadig, Vanessa Lengies, Michelle Nolden, Ashley Newbrough and Carson Kressley.  

Subscribe with Prime Video to stream or buy/rent on Apple TV+.

11. ‘Did you Hear About the Morgans?’ (2009)

A New York couple whose marriage is dwindling witness a murder and are forced to hide out in Wyoming. As a result, their marriage crumbles even more or reignites. 

The movie's lovable cast includes Sarah Jessica Parker, Hugh Grant, Sam Elliot, Mary Steenburgen, Elizabeth Moss, Michael Kelly and Wilford Brimley. 

Rent/buy on Prime Video or Apple TV+.

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10. ‘Over Her Dead Body’ (2008)

A superstitious romantic comedy about a man who deals with the pain of losing his wife on their wedding day. His sister takes him to a psychic in a bid to help him move on. The guy ends up falling for the psychic, but the ghost of his deceased wife begins to haunt them, preventing him from moving on. 

Paul Rudd and Eva Longoria head the movie alongside Lake Bell, Lindsay Sloane, Jason Biggs, Stephen Root, Kali Rocha, William Morgan Sheppard and Sam Pancake.

Buy/rent on Prime Video or Apple TV+.

8. ‘All About Steve’ (2009)

After an amazing blind date, Mary (Sandra Bullock) follows news cameraman Steve (Bradley Cooper) across the country to win his affection. She makes new eccentric friends and discoveries on her outlandish quest for love. 

Joining Bullock and Cooper are Thomas Harden Church, Ken Jeong, DJ Qualls, Keith David, Howard Hesseman, Katy Mixon, Jason Jones, Carlos Gomez, Beth Grant, Keri Kenney, Holms Osborne and M.C. Gainey. 

Stream on HBO Max or rent/buy on Apple TV+ and Prime Video.

7. ‘The Wedding Planner’ (2001)

A fairy tale film about a wedding planner whose fate connects her with a handsome paediatrician after he rescues her from a near-death experience. After they begin to date, she finds out that cupid and her career collide. 

In the cast list, we have Jennifer Lopez, Matthew McConaughey, Justin Chambers, Bridgette Wilson Sampras, Judy Greer, Alex Rocco, Joanna Gleason, Fred Willard, Kevin Pollack, Lou Myers, Charles Kimbrough, Kathy Najimy and Frances Bay. 

Buy/rent on Prime Video and Apple TV+.

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6. ‘The Wedding Date’ (2005)

Portraying the awkwardness accompanying weddings, The Wedding Date narrates the story of a single lady who hires a male escort to be her date for her younger sisters' wedding. The ridiculous move is her attempt to show her ex, who is the groom's best man, that her life is awesome. 

The film's primary cast includes Debra Messing, Dermot Mulroney, Amy Adams, Jack Davenport, Sarah Parish, Jeremy Sheffield, Peter Egan and Holland Taylor.

Rent or buy on Apple TV+ and Prime Video.

5. ‘Date Movie’ (2006)

Hopeless romantic Julia (Alyson Hannigan) falls madly in love with British gentleman Grant Fonkyerdoder (Adam Campbell). But their journey to the altar is faced with many hurdles, including Julia's jealous best friend, whose set on destroying their wedding. 

Besides the leads, we have Jennifer Coolidge, Fred Willard, Eddie Griffin, Tony Cox, Sophie Monk, Judah Friedlander, Carmen Electra, Meera Simham, Tommy Lenk, Marie Matiko and Tom Fitzpatrick. 

Stream Date Movie on Hulu or rent/buy on Apple TV+.

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4. ‘Made of Honor’ (2008)

A commitment-phobe guy unearths that he’s in love with his female best friend just when she’s planning to wed someone else. He seizes the opportunity to break up the wedding after she asks him to be among her bridal party. 

Made of Honor stars Patrick Dempsey, Michelle Monaghan, Kevin McKidd, Kathleen Quinlan, Sydney Pollack, Kadeem Hardison, Whitney Cummings, Busy Phillips, Kevin Sussman, Chris Messina, Richmond Arquette, Emily Nelson, Beau Garrett and James B. Sikking. 

Find the movie on Netflix or buy/rent it on Apple TV+ or Prime Video.

3. ‘My Life in Ruins’ (2009)

A heartfelt romantic comedy about a Greek tour guide who has lost her mojo. As she guides her ragtag travel clients through Greece, she begins to see life from a new perspective and eventually finds her 'kefir'. 

Rounding up the casts are Nia Vardalos, Richard Dreyfuss, María Adánez, Rachel Dratch, María Botto, Alexis Georgoulis Harland Williams, Caroline Goodall, Alistair McGowan, Bernie Stegers and Sheila Bernette. 

Watch the film on HBO Max or rent/buy on Apple TV+ and Prime Video.

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2. ‘What Happens in Vegas’ (2008)

An obnoxious film about career woman Joy McNally (Cameron Diaz) who marries playboy Jack Fuller (Ashton Kutcher) on a drunken night in Las Vegas. Adamant judge withholds their prize money and refuses to annul their marriage. They are forced to make their impromptu marriage work if they are to claim the prize money. 

The movie's star-studded cast includes Rob Corddry, Lake Bell, Treat Williams, Dennis Farina, Jason Sudeikis, Dennis Miller, Zach Galifianakis, Michelle Krusiec, Dierdre O'Connell, Krysten Ritter, Queen Latifah and Andrew Daly.

Stream on HBO Max or rent/buy on Apple TV+ or Prime Video.

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1. ‘The Ugly Truth’ (2009)

A hysterical flick about the battle of the sexes, The Ugly Truth features a lovelorn TV producer who needs the help of her loathsome client, a capricious TV celebrity (host of The Ugly Truth Show), to seduce her newfound boyfriend into falling madly in love with her. Though his immodest game plan works, she eventually realizes that her boyfriend only loves an untrue version of herself. 

The Ugly Truth hosts Katherine Heigl, Gerard Butler, Eric Winter, Bree Turner, Nick Searcy, John Michael Higgins, Cheryl Hines, Kevin Connolly, Bonnie Somerville, Yvette Nicole Brown, Nathan Corddry and Noah Matthews. 

Buy/rent the movie on Apple TV+ or Prime Video.

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