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

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  (#1) Never Been Kissed

  • Jessica Alba, Drew Barrymore, James Franco, Leelee Sobieski, John C. Reilly, David Arquette, Molly Shannon, Octavia Spencer, Marley Shelton, Garry Marshall, Jordan Ladd, Michael Vartan, Marissa Jaret Winokur, Chali 2na, Cut Chemist, Allen Covert, Jeremy Jordan, Cress Williams, Andrew Wilson, Sean Whalen, Cory Hardrict, David Doty, Sara Downing, Alex Solowitz, Giuseppe Andrews, Gregory Sporleder, Tracy Reiner, Jenny Bicks, Philip Hawn, Kathleen Marshall, Branden Williams, Marcello Robinson, Andrew Aguilar, Carmen Llywelyn, Chad Todhunter, Daniel Louis Rivas, Martha Hackett, Denny Kirkwood, Hunter G. Williams, Kevin Scott Greer, Priscilla Cory, A. David Burleigh, Don Snell, Joe Ochman, Russell Bobbitt, Raul Pacheco, Maya McLaughlin, Sarah DeVincentis, Tinsley Grimes, Jason Weissbrod, Marq Edwards, David Douglas, Asdru Sierra, Mike Moyer, William Marrufo, Niesha Trout, Derek Morgan, Katie Lansdale, Rock Reiser, Jose Espinosa, Fabio May, Billy McLellan, Danny Zavatsky, Wil-Dog Abers, Justin Porée, Chad Haywood, Ulises Bella, Jiro Yamaguchi, Amanda Wilmshurst, Steven Wilde, Tara Skye, Jennifer Parsons, Joshua Fitzgerald, Conor O'Neil, Mark Allen

  Josie (Drew Barrymore) is a 25-year-old undercover journalist posing as a high school student to write about life as a modern teen. Although pretending to be a teenager is questionable in any context, what makes the decision truly disturbing is the fact that her English teacher Sam (Michael Vartan) falls in love with her.

  Regardless of their attraction to each other, Sam is under the impression that Josie is a teenager under his supervision. 
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  (#2) Grease

  • John Travolta, Olivia Newton-John, Stockard Channing, Sid Caesar, Joan Blondell, Lorenzo Lamas, Michael Biehn, Eve Arden, Frankie Avalon, Jeff Conaway, Didi Conn, Dinah Manoff, Alice Ghostley, Fannie Flagg, Wendie Jo Sperber, Andy Tennant, Dody Goodman, Eddie Deezen, Michael Tucci, Annette Charles, Darrell Zwerling, Sandra Gray, Ellen Travolta, Kelly Ward, Edd Byrnes, Jon Bauman, Dennis Cleveland Stewart, Frederick "Dennis" Greene, Jamie Donnelly, Mimi Lieber, Susan Buckner, Barry Pearl, Scott Simon, Greg Bradford, Dick Patterson, Greg Rosatti, Helena Andreyko, Bob Quinn, Johnny Contardo, Dennis Daniels, Donald York, Lou Spadaccini, Antonia Franceschi, John "Jocko" Marcellino, Sean Moran, Carol Culver, John Robert Garrett, Kristine Greco, Richard Weisman, Lennie Baker, Daniel Levans, Paula Beyers, Judy Susman, Andy Roth, Jennifer Buchanan, Larry Dusich, Cindy DeVore, Vinny Genna, Barbi Alison, Deborah Fishman, Carole Demas, John Mooney, Tod Burton, Donna Felix, J. Andrew Kenny, Lora Marie Oberhofer Taylor

  Straight-laced Sandy (Olivia Newton-John) and bad boy Danny (John Travolta) are from two very different worlds. But by the end of Grease, Sandy decides to change her wardrobe and her personality to win Danny's heart. 

  Gone is the goody-two-shoes and in her place is a cigarette-smoking, big-haired dominatrix. Altering key aspects of yourself and your personality are not hallmarks of a lasting relationship, but in the rom-com universe, Sandy's metamorphosis means her and Danny get to live happily ever after. 
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  (#3) My Best Friend's Wedding

  • Julia Roberts, Dermot Mulroney, Rupert Everett, Cameron Diaz, Paul Giamatti, Rachel Griffiths, Harry Shearer, Carrie Preston, Susan Sullivan, Bree Turner, M. Emmet Walsh, Philip Bosco, Christopher Masterson, Chelcie Ross, Paul Adelstein, Charlie Trotter, Rose Abdoo, Mike Bacarella, Robert Minkoff, Davenia McFadden, Joe Sikora, Burton Zucker, Charlotte Zucker, Nydia Rodriguez Terracina, Reese Foster, Anh Duong, Daisy Alexandra Sylbert-Torres, Lucy Pacquet, Ned Schmidtke, Gene Janson, Susan Breslau, JoBe Cerny, Sid Hillman, Mara Casey, Chris Lowe, Jerod Howard, Mary-Pat Green, Johnny White, Patricia E. Harrington, Mark Swenson, Kathi Copeland, Dominic Testa, Renata Scott, Tonray Ho, Amy Danles, Phillip Ingram, Jennifer McComb, Jo Farkas, Kevin Michael Doyle, Ray Uhler, Maridean Mansfield Shepard, Eric A. Pot, Molly Murphy, Anne Spradley-Montie, Kelly Sheerin, Leon 'Lee' Fuller, Shirley Kelly, Stephanie Burton, Jennifer Garrett, Shale Marks, Robert Velo, Michelle Hutchison, Norman Merrill, Raci Alexander, Larry Santori, George Bozonelos, Robert Sutter, Loretta Paoletti, Guillermo Tellez, Sharon Haight, Scott Kuhagen, Aida Baggio, Cassie Creasy

  Julianne (Julia Roberts) makes so many bad decisions in My Best Friend's Wedding that even First Lady Hillary Clinton took the time to castigate her publicly. The whole premise of the movie is based on an unwise decision: Julianne is bent on doing whatever it takes to sabotage the relationship between her best friend, Michael (Dermot Mulroney), and his fiancée, Kimmy (Cameron Diaz). 

  The laundry list of Julianne's bad choices includes forging an email that gets Michael fired, telling Michael that she is engaged to her gay pal George, and kissing Michael on the day of his wedding. Everything turns out okay in the rom-com world, although in reality, Julianne might have ruined more than a few relationships. 
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  (#4) Jerry Maguire

  • Tom Cruise, Lucy Liu, Renée Zellweger, Troy Aikman, Kelly Preston, Michael Irvin, Cuba Gooding Jr., Warren Moon, Emily Procter, Jonathan Lipnicki, Katarina Witt, Drew Bledsoe, Jay Mohr, Regina King, Glenn Frey, Dan Dierdorf, Eric Stoltz, Jerry Cantrell, Jerry O'Connell, Bonnie Hunt, Kerry Collins, Drake Bell, Beau Bridges, Frank Gifford, Art Monk, Stacey Williams, Brent Barry, Ki-Jana Carter, Ivana Miličević, Johnnie Morton, Al Michaels, Rick Mirer, Donal Logue, Aries Spears, Herman Moore, Summer Sanders, Rich Kotite, Tim McDonald, Jeffrey Lurie, Jim Irsay, Winnie Holzman, Mike Tirico, Rebecca Rigg, Kenneth Keith Kallenbach, Jann Wenner, Wayne Fontes, Drew Rosenhaus, Alexandra Wentworth, Hynden Walch, Reagan Gomez-Preston, Rob Moore, Toby Huss, Justina Vail Evans, Roy Firestone, Christine Cavanaugh, Gina La Piana, Todd Louiso, Leigh Steinberg, Kelly Coffield Park, Mark Pellington, Jacqueline Collen, Angela Goethals, Jeremy Suarez, Mia Korf, Mel Kiper Jr., Peg Phillips, Jerry Ziesmer, Jeff Moorad, Lisa Rotondi, Dean Biasucci, Alice Marie Crowe, David Ursin, Micki Duran, Jason H. Karniol, Michael Kehoe, Tom Gallop, Sean Patrick Reilly, Lisa Ann Hadley, Lynnanne Zager, Andrea Ferrell, E. Lamont Johnson, Jordan Ross, Jared Jussim, Iva Franks Singer, Larina Adamson, Mike Boss, John Cramer, Anthony Natale, Steve J. Termath, Alison Armitage, Joseph Neibich, Russel Lunday, Kerry Friend, Lisa Stahl, Nada Despotovich, Rod Tate, Amaryllis Borrego, Lightfield Lewis, Samantha Smith, Kari Keegan, Klair Bybee, Mike White, Benjamin Kimball Smith, Dallas Malloy, Matt von Siegel, Charley Gilleran, Leslie Upson, Susan Norfleet, Kirsten Krueger, Golan Ramras, Thomas J. Reilly, Christopher J. Smith, Jeff Dolniak, Theo Greenly, Carolyn Renee Smith, Coleman McClary, Sean Neff, Joanna Daniels, Erica Sorgi, Dennis Fitzgerald, Jenny Worman, Thomas James Kepner, Michael James Johnson, Danny Rimmer, David Spring, Charlie Cronin, Lisa Amsterdam, Lauren Parker, Ryan Langdon, Stan Sessoms, Sascha Lorren, Gale Hillman, Heather Cheney, Jim Moffatt, Shannon Thornton, Golde Starger, Stephanie Furst, Beaumont Bacon, Luis Damian, Valerie Richards, Jody Collins, June Saruwatari, Alberto Alfavo, Cha-Cha Sandoval, Diana Jordan, Brandon Christianson, Jesus Alberto Guzman, Leo Zick, Susan Pingleton, Kymberly Kalil, Joseph B. Henry, Tom Friend, Ingrid Beer, Meg Coyle, Evelyn Fontes, Juan Arnoldo Morales, Kevin McNally, Rick Johnson

  Dorothy (Renée Zellweger) makes a few bad decisions over the course of her relationship with the title character, Jerry Maguire (Tom Cruise). First, the single mother quits her stable job to follow Jerry to his startup.

  Next, when the startup falters, she has an opportunity to take a stable job with benefits elsewhere. However, Jerry proposes to her to get her to stay, and she says yes.

  Finally, Jerry treats her terribly, only to come to her in the eleventh hour and apologize. Of course, she forgives him because he, "had her at hello."

  Please. 
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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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  (#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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  (#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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  (#8) While You Were Sleeping

  • Sandra Bullock, Monica Keena, Bill Pullman, Ally Walker, Peter Boyle, Jack Warden, Peter Gallagher, Glynis Johns, Rick Worthy, Michael Rispoli, Jason Bernard, Dick Cusack, Mike Bacarella, Susan Messing, Peter Siragusa, Margaret Travolta, Micole Mercurio, Shea Farrell, Kate Reinders, Bernie Landis, Marc Grapey, Gene Janson, Ann Whitney, Dobie Maxwell, Marcia Wright, Kevin Gudahl, Richard Pickren, Thomas Q. Morris, Megan Schaiper, James Krag, Krista Lally, Ruth Rudnick, Joel Hatch

  Lucy (Sandra Bullock) is mistaken as Peter Callaghan's (Peter Gallagher) fiancée while he's in a coma, a ruse she chooses to go along with for reasons that remain unexplained. She befriends Peter's family, including his bother, Jack Callaghan (Bill Pullman). Eventually and inevitably, Jack and Lucy fall in love, creating a problem for the young woman who is falsely engaged to her new love interest's brother.

  You'd think Lucy's decision to lie about her identity would be a problem for Jack and the rest of the Callaghan clan, but, in the rom-com universe, her sweet and charming demeanor is enough to win the hearts of everyone. 
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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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  (#10) Something's Gotta Give

  • Jack Nicholson, Keanu Reeves, Diane Keaton, Amanda Peet, Frances McDormand, Jon Favreau filmography, KaDee Strickland, Rachel Ticotin, Paul Michael Glaser, Nichole Hiltz, Lorna Scott, Vanna Bonta, Peter Spears

  Something's Gotta Give gets to its happily-ever-after via a really bad decision. Erica (Diane Keaton) dates, falls in love with, and marries her daughter's ex-boyfriend, Harry (Jack Nicholson). Harry is 63 and dating 29-year-old Marin (Amanda Peet). He falls for Marin's mother while she is nursing him back to health. Although Harry and Marin have broken up by the time Erica becomes involved with the aging playboy, dating your daughter's ex is a questionable parenting move, to say the least.

  The last scene of the film wants us to believe that everything is hunky-dory, but there must be some awkwardness at family functions.
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  (#11) The Proposal

  • Sandra Bullock, Ryan Reynolds, Betty White, Malin Åkerman, Mary Steenburgen, Mini Andén, Craig T. Nelson, Denis O'Hare, Niecy Nash, Aasif Mandvi, Michael Nouri, Anne Fletcher, Oscar Nunez, Gregg Edelman, Stream, Ellen Becker Gray, Dan Marshall, Michael Mosley, Larry Vigus, Shawn Fogarty, John Franchi, Dale Place, Naeem Uzimann, Jerrell Lee, Desiree April Connolly, Robert Masiello, Donna Glee Reim, Mary Linda Rapelye, Kate Lacey, Patrick Mel Hayes, Jodie Brunelle, Vyvian B. Stevens, Haytham Kandil, Alexander Garde, David Struffolino, Darren Ross, Rich Skinner, Brian Bradbury, Ylian Alfaro Snyder, Phyllis Kay, Dan Griffin, Adam Zalt, Chemi Che-Mponda, Kortney Adams, Frankie Imbergamo, Thomas Olson, Ron Murphy, Eric Ryan, Cindi Alex, Annie Rohling, Cory Scott, Nikki Preston, Alicia Hunt, Sophya Gudelman, Cory Rasmussen, Eric Ferraz, Ben L. Mitchell, Diane Curran, Gene Fleming, B. Johnson, Alexis Garcia, Chris Whitney, Joseph Guglielmo, G.A. West

  Margaret (Sandra Bullock) is a Canadian who needs to stay in the US, so she makes the questionable decision to enter into a green card marriage with her assistant Andrew (Ryan Reynolds). It all turns out okay, of course, because Margaret and Andrew are actually into each other. But questionable choices are a theme with this couple.

  Margaret offers Andrew a promotion in exchange for agreeing to the marriage. This poses ethical questions. Then there's the fact that if Margret and Andrew are caught engaging in immigration fraud, they could be fined $250,000 and sentenced to five years in the pokey. 
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  (#12) Fever Pitch

  • Drew Barrymore, Jimmy Fallon, Stephen King, John Olerud, Dennis Eckersley, Johnny Damon, JoBeth Williams, KaDee Strickland, Tim McCarver, Jim Rice, Charlotte Sullivan, Joe Buck, Ione Skye, Jason Varitek, Siobhan Fallon Hogan, Marissa Jaret Winokur, Harold Reynolds, Willie Garson, Steve Levy, Scott Rosenberg, Lenny Clarke, Jack Kehler, Jackie Burroughs, Trot Nixon, Andrew Wilson, Eric Bruno Borgman, James Sikking, Armando Riesco, Danny Murphy, Russ Jaquith, Johnny Cicco, Stream, George King, Don Orsillo, Zen Gesner, Jason Spevack, Jeanne Zelasko, Elizabeth Alexander, Peter Gammons, Daniel Greene, Martin Roach, Joe Castiglione, Matt Watts, Mark Ciardi, Darren Frost, Paul McGuire, John Boylan, Shawn Fogarty, Frank D'Agostino, Adam Bagni, Johnny Sneed, Lorre Fritchy, Ed O'Keefe, Elisangela DiAlencar, Carl Beane, Grady Justice, Brett Murphy, Anna Byers, Bob Weekes, Michael Rubenfeld, Janet Borgman, Bart Bedford, Quancetia Hamilton, J.C. Kenny, Greta Onieogou, Daniel Joseph, John-Eliot Jordan, Preston Thomas, Jesse Peter, Jack Andrade, Mariann Neary, Docky, Laurel Astri, Brandon Craggs, Anthony M. Pizzuto, John Ruggiero, Gina Clayton, Brian Hayes Currie, Shana Carr, John Currie, George Ghali, Matthew Peart, Bob Lobel, Warren Tashjian, Emily O'Donnell, Ray Valliere, Brad Blank, Nick Purcell, Wayne Flemming, Keegan O'Donnell, Alexandra McDougall, Jerry Quinn, John Pungitore, Paul Palandjian, Evan Helmuth, Steve Scarfo, Rick Cordeiro, Don Gavin, Robert Mason, Shary Guthrie, Isabella Fink, Tommy Jordan, Keith MacWhorter, Mari Cocoran, David Klar, Ron "Puppy" Cavallo, Joe Sobalo Jr., Ken Gagne, Jessamy Finet, Matthew Nagle, Erin Nanstad, Howard Nickerson, Maureen Keiller, Miranda Black, Daniel Cummings, Jordan Leandre, Mike Steedman, Kenny Rogerson, Bobby Curcoro, Melinda Lopez, Brenda Flynn, Glenn W. Kane, Geoffrey Williamson, Lucy Bidwell, Stacey Lucchino, Tod Abbrecht, Corey Sands, Marla Angermeier, Jermaine Plummer, Rick Cohen, Sharlene Yuen, Scott Desano, Sam Caswell, Amie James, Bobbi Stoler, Bob Sands, Joan Macleod-Follows, Matt Melina, Monica Niedermeyer, Davis Ballard, David Rosenberg, Blair Ballard, Mark Andrada, Meda Thomas, Christine Ford, Jenna Caswell, Jaime P. Ford, Diana O'Donnell, Alison Novelli, Sam Dissanayake, Scott Severance, Stephen Kyle, Andrew Steedman

  Lindsey (Drew Barrymore) can't reach Ben (Jimmy Fallon) from where she sits at Fenway Park, but he is about to sell his season tickets, and she has to prevent that from happening. So, she barrels onto the field to stop him and declare her love, evading security guards in the process. It makes for a sweet ending, but her decision to storm onto a professional playing field is not very well thought out. 

  Punishment for running onto the field during a pro sporting event can result in serious penalties, including a $1,000 fine, a night in jail, and a lifetime ban from the park. This is especially terrible considering Ben is a diehard Sox fan. 
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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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  (#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. 
• 

  (#15) 13 Going on 30

  • Jennifer Garner, Ashley Benson, Mark Ruffalo, Renee Olstead, Judy Greer, Andy Serkis, Lynn Collins, Brie Larson, Jim Gaffigan, Scout Taylor-Compton, Christa B. Allen, Kathy Baker, Carmit Bachar, Maz Jobrani, Kimberly Wyatt, Gia Mantegna, Tyce Diorio, Mary Pat Gleason, Robinne Lee, Sarah Loew, Nadine Ellis, Joe Grifasi, Brittany Curran, David Boston, Kiersten Warren, Sean Marquette, Susan Egan, Philip Pavel, Marcia DeBonis, Sara Swain, Phil Reeves, Kevin Stea, Larry Vigus, Alexandra Kyle, Nancy O'Meara, Samuel Ball, Candace Elaine, Adrian Armas, Alex Black, Ward Horton, Nicole Abisinio, Brad Tiemann, Amber Gristak, Stacey Harper, Julia Roth, Rita Bland, Sydni Beaudoin, Irena A. Hoffman, Caroline A. Rice, Corena Chase, Ian Barford, Jason Yribar, Natalie Willes, Timothy Anderson, Bill Kotsatos, Eron Otcasek, Catherine Combs, Crystal Michelle, Bubba Dean Rambo, Darrel W. Wright, Janina Garraway, Mario Simone, Benita Nall, Michon Suyama, Richard Whitebear, James Pomichter, Justin Burke, Kadee Sweeney, Michael Tommer, Melody Krell, Luis Pedron, Madeline Sprung-Keyser, Shambo Pfaff, Jeffrey Shane Cohn, Megan Lusk, George Hine, Katie Miller, Fabrice Calmettes, Michael William Higgins, Kevin D. White, Jason Makely, Douglas Caldwell, John W. Grant

  After a bad reaction to some magic pixie dust, Jenna (Jennifer Garner) goes from being a 13-year-old to a successful 30-year-old Manhattan yuppie overnight. She is eventually restored to her adolescent self, but as we see in the final few moments of the movie, she eventually marries her middle school sweetheart, Matty (Mark Ruffalo). We can assume, then, that Jenna never experiences what it's like to be a young, single adult. She never has the adventures and misadventures that come with dating. She doesn't get the opportunity to know herself on her own in the world.

  There is something to be said for a storybook romance, but this rom-com plot is not very realistic when it comes to long-term love. 

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