Random Objectively Worst Decisions In Rom-Com History (15 items)

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  (#14) The Holiday

  • Lindsay Lohan, Cameron Diaz, Kate Winslet, James Franco, Jude Law, Dustin Hoffman, Jack Black, Odette Annable, Eli Wallach, John Krasinski, Shannyn Sossamon, Alex O'Loughlin, Rufus Sewell, Edward Burns, Kathryn Hahn, Bill Macy, Shelley Berman, Sarah Parish, Nikki Novak, Judith Drake, Arne Starr, Lydia Blanco, Jay Simpson, Nicholas Downs, Leanne Wilson, Miffy Englefield, Pamela Dunlap, Kenneth Danziger, Jon Prescott, Hal Douglas, Patrick Cavanaugh, Mark A. Nash, Freddie De Grate, Jacob Head, Jamie McCall, Hope Riley, Patrizia Barretto, MarLee Candell, Steven Bruns, Emma Pritchard, Gilbert Esquivel, Justin Collins, Andy Gates, Scott Slifer, Darline Harris, Sarah Flind, David Venafro, Marina Morgan, Terry Diab, Marcell Brown, Bundle Williams, Lynden Edwards, Suzanne Dizon, Siobhan Pestano, Charles Dinsdale

  In the 2006 film, The Holiday, two strangers, Amanda (Cameron Diaz) and Iris (Kate Winslet), switch houses over the holidays to escape their failed relationships and disastrous love lives. Although they meet on a home-exchange website, the circumstances are much more complex and questionable than booking an Airbnb for a winter getaway. 

  There is a big risk in traveling to a different continent with no guarantee that the home you're staying in is real, or that you aren't renting your place to a serial killer. 
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  (#5) 27 Dresses

  • Katherine Heigl, Malin Åkerman, Krysten Ritter, Judy Greer, James Marsden, Melora Hardin, Edward Burns, Brian Kerwin, Maulik Pancholy, Alexa Havins, Alecia Batson, Erin Fogel

  Once perpetual bridesmaid Jane (Katherine Heigl) realizes she is in love with Kevin (James Marsden), she crashes a wedding to tell him how she feels. Not content to wait until the event is over, she interrupts the wedding and declares her love in front of a roomful of perplexed strangers. 

  Imagine spending thousands of dollars on your special day only to have a Katherine Heigl character hijack it to make a personal announcement about her own love life. 
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  (#7) How to Lose a Guy in 10 Days

  • Kate Hudson, Matthew McConaughey, Bebe Neuwirth, Marvin Hamlisch, Kathryn Hahn, Shalom Harlow, Michael Michele, Thomas Lennon, Robert Klein, Adam Goldberg, Annie Parisse, Marv Albert, Celia Weston, Natalie Madison-Brown, Tony Longo, Georgia Craig, William Duell, Ingrid Hart, Liliane Montevecchi, James Murtaugh, Warner Wolf, Justin Peroff, John DiResta, William Hill, Radio Man, Andrew Moodie, David Macniven, David C. Roehm Sr., Diego Fuentes, Julie McLeod, James Mainprize, Al Bernstein, Doug Murray, Gina Sorell, Samantha Quan, Jeff Gruich, Scott Benes, Zachary Benes, Rebecca Harris, Ross Gallo, Collin Barrett, Jody Raymond, Gery Soles, Bob Reeves, Rod MacDonald, Frank Penny, Bruce Farquhar, Jim Paris, Ames Adamson, Archie MacGregor, Randy Kerdoon

  This movie is rife with bad decisions, from Ben (Matthew McConaughey) taking Andie (Kate Hudson) to meet his family after a very brief courtship, to Andie pushing Ben away for the sake of a magazine article.

  Ben exercises his worst judgment, however, when he makes the pompous assertion that he can get any woman to fall in love with him. His boss responds with a similar lack of forethought, offering Ben a coveted ad campaign if he can, indeed, accomplish that feat within 10 days. Not surprisingly, Ben accepts the offer. Call it toxic masculinity; call it a silly setup begging for trouble and an inevitably romantic ending. It's still a bad business decision to hand out promotions based on an employee's love life. 
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  (#9) Kate & Leopold

  • Hugh Jackman, Meg Ryan, Liev Schreiber, Viola Davis, Natasha Lyonne, Kristen Schaal, Shalom Harlow, Breckin Meyer, Spalding Gray, Charlotte Ayanna, Craig Bierko, Bradley Whitford, Philip Bosco, Monique Gabriela Curnen, Domenick Lombardozzi, John Rothman, Arthur J. Nascarella, Matthew Sussman, Paxton Whitehead, Martha Madison, David Aaron Baker, Cole Hawkins, Josh Stamberg, Kevin Daniels, Del Pentecost, Ebony Jo-Ann, Francis Dumaurier, Aimee Denaro, Andrew Jack, Peggy Flood, Meg Gibson, Eddie Marrero, Hu Nai-yuan, Gary Beck, Diana Brownstone, Stephanie Sanditz, Carl Burrows, Todd Poudrier, Fabrizio Fante, Chazz Menendez, Bill Corsair, Joe Mosso, Ray Seiden, Roma Torre, Elizabeth Logan, Lee Burkett, Howard Feller, Brian Letscher, Jonathan Fried, Stan Tracy, Brandon Parrish, Bart DeFinna, Daphna Cardinale, Matthew Beisner, Frank Arcuri, William Sanford, Robert Ray Manning Jr., Jennifer Johns, Celia A. Montgomery, Brittney Startzman, George Hahn, Henry Boyle, Jorjeana Marie, Andrea Barnes, Dennis Rees, Stephanie Montalvo, Michael Cassady, Russell Di Perna, Cornelius Patrick Byrne, Michael Shelle

  Kate & Leopold is a time-travel romance with a happy ending that hangs on one terrible decision. Kate (Meg Ryan) meets the third Duke of Albany, Leopold (Hugh Jackman), who travels to modern-day New York City from 1876 via a temporal portal at the Brooklyn Bridge.

  Confusion and culture clash unfold before the couple falls in love and Kate willingly forgoes her life in the modern world to marry Leopold in 1876 - before women have the right to vote, control their own bodies or finances, or work in certain fields. 
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  (#13) Clueless

  • Alicia Silverstone, Brittany Murphy, Paul Rudd, Stacey Dash, Wallace Shawn, Billy West, Donald Faison, Mike Judge, Amy Heckerling, Breckin Meyer, Dan Hedaya, Jeremy Sisto, Nicole Bilderback, Julie Brown, Carl Gottlieb, Jace Alexander, John Kricfalusi, Elisa Donovan, Twink Caplan, Sam Maccarone, Joseph D. Reitman, Roger Kabler, Micki Duran, Michael Klesic, Gregg Russell, Jermaine Montell, Justin Walker, Aida Linares, Ron Orbach, Sean Holland, Herb Hall, Bobbie Sunday Starr, Josh Lozoff, Christopher E. Cooper, Danielle Eckert, Anthony Beninati, Susan Mohun, Craig Ponder, Sabastian Rashidi

  Cher (Alicia Silverstone) and Josh (Paul Rudd) are not technically related. Their parents were married for five years but divorced before the start of the film. Regardless, there is still something unsettling about dating someone who was formerly a part of your family, no matter how tangentially.

  Cher is notably clueless, but Josh, who is older and studying to be a lawyer, should probably know better than to date his teenage ex-stepsister. 
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  (#6) Runaway Bride

  • Julia Roberts, Richard Gere, Christopher Meloni, Joan Cusack, Sela Ward, Rita Wilson, Laurie Metcalf, Garry Marshall, Larry Miller, Sandra Taylor, Donal Logue, Héctor Elizondo, Paul Dooley, Yul Vazquez, Linda Larkin, Lisa Roberts Gillan, Tom Mason, Kathleen Marshall, Reg Rogers, Shannon Wilcox, Gregg Goulet, Ryan Slattery, Patrick Richwood, Jane Morris, Jean Schertler, Scott Marshall, Diana Kent, Barbara Marshall, Tom Hines, Jacqui Allen, Julie Paris, Tiffany Paulsen, Allan Kent, Dina Napoli, Marty Nadler, Yvonne Pollack, Diane Frazen, Kevin Murray, Rebekah Hoyle, Joy Rosenthal, Garrett Wright, Robert Lee Jones, James Richardson, Carol DePasquale, Joseph Williams Andrews, John Goldman, Duncan Lam, Cheryl Frazel, William Todd Crosby, Eugene Walker Jackson Jr., Karla Pattur, Tom Cutler, Lee McKenna, Thong Nguyen, Karen Stirgwolt, Jack Hoffman

  Before hitting it off with a columnist named Ike (Richard Gere), Maggie (Julia Roberts) leaves not one, not two, but three fiancés at the altar. How much money did Maggie's family lose with each of those weddings (all of which were grand affairs)? 

  She might have considered a courthouse marriage, which averages between $25 and $75.

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