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The Top Ten Valentine’s Day Movies for Single (and Quite Possibly Bitter) 20-Something Women

Posted by Hermione,   Feb 6, 2003

Well, girls, it looks as though it’s that time again. No matter what we might fabricate about Valentine’s Day being some manufactured holiday to increase consumerism during the lull between Christmas and Easter, deep down every single girl feels a bit of a yearning when all those red and pink hearts start appearing and she knows that she’s going to be spending the holiday alone for yet another year. Whether you call it Devil’s Day, or whether you look forward to spending some quality time with your single girlfriends, I present to you ten chick flicks guaranteed to make you smile…no matter how bitter you might happen to be.


Merriam-Webster’s Dictionary defines vicariousness as “[something] experienced or realised through imaginative or sympathetic participation in the experience of another.” I, on the other hand, define it as “a way of life.” That’s right; if your life reeks of routine, of boredom, of everything that you once imagined it wouldn’t be, what law is there to tell you that you can’t capitalise off of other people’s happiness to create your own? It may not be the most psychologically healthy of things, but if it takes care of that edge of loneliness, then it works for me. What better way is there to live vicariously, then, than to do so through the lives of non-existent characters? I mean, if you’re going to be certifiable, might as well go that extra mile and guarantee a long life in the comforts of a long-sleeved jacket that straps at your back, right?

Romantic movies make us smile because no matter how sane we might happen to be, a part of us imagines us in that same situation with the man of our dreams. Wherever your romantic tastes might run, what follows are the staples of romantic film over the past twenty years. Whether you watch them alone or with a friend, these are films that every woman should have in her video collection.

10. SOME KIND OF WONDERFUL

Starring: Eric Stoltz, Mary Stuart Masterson, Craig Sheffer, Lea Thompson

Director: Howard Deutch

Writer/Producer: John Hughes

Circa 1987

Hermione’s Rating: 3.5 stars

John Hughes is popular for what is commonly known as “teenage fluff” where the geek ends up with the popular boy/girl in school. Anyone who ever had a crush on someone in the popular crowd can’t help but to be drawn to Hughes’ movies where, for once, the good guy/girl doesn’t finish last.

Some Kind of Wonderful is the story of Keith Nelson (Stoltz), a social outcast who spends his time earning money as a mechanic in a garage, being pressured by his father to go to college, and spending time with his tomboy best friend Watts (Masterson). Keith’s true passion, however, is for art…and for Amanda Jones (Thompson), the prettiest girl in school. When he decides to pursue Amanda, Keith is not only surprised that she agrees to go out with him, but even more so that just when he thought all his dreams had come true, he begins to see his best friend as though for the first time and realises that maybe it’s not the popular girl who he’s really been in love with all along.

The Bottom Line: The movie is pretty cheesy, and Thompson’s character has a tendency to grate on your nerves, but the moments between Stoltz and Masterson are natural endorphin releasers. The film is strangely addictive, and although it was one of Hughes’ most vituperated films it is nonetheless very entertaining and a nice warm-up for any girls’ night in.

9. LOVE POTION No.9

Starring: Sandra Bullock, Tate Donovan

Writer/Director: Dale Launer

Circa 1992

Hermione’s Rating: 3.0 stars

The story of scientist Paul Matthews (Donovan) who, upon being urged by his friends to consult a gypsy fortune-teller in order to cure him of his single status, discovers the secret to making members of the opposite sex fall at his feet, Love Potion No. 9 is not only charming, but it’s funny as well.

When Matthews is given a paste which, when in solution, enables him to minutely affect his vocal patterns in order to make women fall in love with him with a single word, he immediately brings it to fellow scientist Diane Farrow (Bullock) in order to more closely examine the phenomenon. The two scientists, both unlucky in romance, decide to test the solution on themselves to see how many people they can attract…all in the name of science of course. They’re so busy making other people fall in love with them, however, that they don’t have time to realise that they’ve in fact fallen in love themselves…with each other.

The Bottom Line: The film is definitely entertaining, but the most entertaining aspect of it isn’t necessarily the romance but the transformation Bullock undergoes from buck-toothed, bushy-haired nerd to beautiful, modern-day woman. The film has its slow moments in the beginning, but by the end it will have succeeded in charming everyone in the room.

8. SIXTEEN CANDLES

Starring: Molly Ringwald, Michael Schoeffling, Anthony Michael Hall

Writer/Director: John Hughes

Producer: Hilton Green

Circa 1984

Hermione’s Rating: 3.5 stars

Another John Hughes movie, and another classic geek-gets-god fairytale.

Samantha Baker is turning sixteen and her entire family has forgotten her birthday due to their preparations for her older sister’s nuptials. Ever the melodramatic teenager, Samantha thinks her life is over; not only has everyone forgotten to wish her a sweet sixteen, but her chest is still flat, she’s still boyfriendless, and her grandparents have taken over her bedroom. The only light in Samantha’s life is Jake Ryan, the most unattainable boy in school. Not only is Jake a senior who would never give Samantha a second (let alone a first) glance, he is also dating a curvy blonde and the goddess to his god-like presence.

Just when it would seem that Samantha’s life has finally come to an end (the school geek (Hall) keeps making a nuisance of himself and accidentally embarrasses her at a school dance), Jake takes notice of Samantha and starts asking around about her. Oblivious to this change of circumstances, however, Samantha can only keep wishing that her life will change…until it finally does.

The Bottom Line: The acting is all around pretty bad, I’m afraid, but it’s funny to watch all these actors when they were young. Any Molly Ringwald film is worth a watch, and it’s amusing to see John Cusack when he was still a lanky, nerdy kid. Being able to gawk at Michael Schoeffling (who pretty much disappeared off the face of the earth after doing Wild Hearts Can’t be Broken) is, on its own, reason enough to see this film.

7. SLIDING DOORS

Starring: Gwyneth Paltrow, John Hannah, Jean Tripplehorn, John Lynch

Writer/Director: Peter Howitt

Circa 1998

Hermione’s Rating: 4.0 stars

Problably not what most girls would consider a “romance movie,” Sliding Doors takes an unconventional approach at getting two people together. The plot is more than just romance, however, and that’s what makes this film worth a see.

Working on the premise that there is a pivotal moment in everyone’s life that dictates their fate, Sliding Doors follows the story of Helen Quilley, a woman who is fired from her job under the pretence that she has been stealing from the company. Helen’s story is split into two storylines, however: that of her catching the London tube home and catching her boyfriend cheating on her, or that of her missing the tube by a mere few seconds and staying oblivious to her boyfriend’s cheating ways.

The Bottom Line: The film is really well done, and it stays away from a lot of the cheese that other romance movies tend to steer towards; Hannah is, as usual, brilliant, though his role is slightly limited. Paltrow also does an excellent job as both newly-freed Helen and still-oblivious Helen. The movie premise might be slightly difficult to understand, but on-screen, Howitt has done a remarkable job of making the audience know exactly what’s going on.

6. WHILE YOU WERE SLEEPING

Starring: Sandra Bullock, Bill Pullman, Peter Gallagher

Director: Jon Turteltaub

Writers: Daniel G. Sullivan, Fredric LeBow

Circa 1995

Hermione’s Rating: 3.5 stars

Anyone who has ever admired someone from afar, without ever having spoken to him/her will find interest in this romantic comedy. Another Sandra Bullock flick.

Lucy Moderatz (Bullock) is a lonely el.-train token collector who spends her days fantasizing about a man (Gallagher) she’s only ever seen at her booth and never actually spoken to. When her mystery man is attacked and thrown on the tracks in front of an oncoming train, Lucy jumps after him and is able to pull him out of harm’s way. Her mystery man, however, remains in a coma. Wanting to check in on him at the hospital, Lucy lies and tells the nurse that she is the man’s fiancée, knowing that only family members are allowed to visit patients. Unfortunately for Lucy, however, her lie spins out of control as the man’s family gets wind of it and welcome her into their family as their new daughter/sister to be.

Lucy is torn between telling the truth and losing the only family she has ever truly known since her father’s death, or keeping the lie alive while her feelings continue to develop…for her mystery man’s brother (Pullman).

The Bottom Line: It came out as a holiday romantic comedy, but the truth of the matter is that it can be enjoyed year-round. There’s a reason why everybody loves Sandy, and this only comes to remind us of why that is. Even Pullman, who isn’t necessarily what one would consider a “leading man” does a great job. It’s definitely cheesy at times, but this is good cheese.

5. NEVER BEEN KISSED

Starring: Drew Barrymore, Michael Vartan, David Arquette, Molly Shannon

Director: Raja Gosnell

Writers: Abby Kohn, Marc Silverstein

Producers: Sandy Issac, Nancy Juvonen

Circa 1999

Hermione’s Rating: 3.0 stars

Here is a film that will bring the nostalgia level through the roof…and it’s just an added bonus that Alias star Michael Vartan happens to play such a big role in it.

Josie Geller (Barrymore) is a copy editor for the Chicago Sun Times newspaper who gets the chance of a lifetime when she gets assigned to work as an undercover reporter pretending to be a student enrolled in high school. Not the most popular in her own day, Josie has a second chance to prove herself among the “popular” group. Of course, that’s not all that Josie has a chance to do. When she starts falling for the young English teacher Sam Coulson (Vartan) it’s all Josie can do to keep on pretending that she’s eighteen years old instead of twenty-five.

The Bottom Line: As far as quality, this is probably the worst of the ten I’ve listed. Barrymore seems to have been miscast and the film is rampant with clichés, but nevertheless it’s one of my favourites. The thought of having a second chance at being popular and knowledgeable and beautiful is one that every high school outcast wishes he/she could have; and, like I said, it’s worth seeing only for the fact that Michael Vartan is h-o-t.

4. THE CUTTING EDGE

Starring: D.B. Sweeney, Moira Kelly, Roy Dotrice

Director: Paul Michael Glaser

Writer: Tony Gilroy

Circa 1992

Hermione’s Rating: 4.0 stars

Well now we’re getting down to the wire; this is the classic boy & girl hate each other, boy & girl fall in love movie. This is an ultimate chick flick. No self-respecting guy will ever sit through this one alone and that, on its own, is proof that you will love it.

Douglas Dorsey (Sweeney) is on the up-and-up in the world of hockey until, at an Olympic match, he is hit and loses peripheral vision in one eye. Finished in the hockey world, Doug is in the throes of despair until skating coach Anton Pamchenko (Dotrice) approaches him. Enthusiastic at first, Doug is much less so when he finds out that Pamchenko is a skating coach, all right…a figure skating coach. At the end of his rope and willing to give anything a try, Doug agrees to follow Pamchenko to visit his would-be skating partner: one hot-headed Kate Mosley.

The chemistry between Doug and Kate is obvious from the very beginning: they can’t stand each other. Both are hardheaded, and both are unwilling to give the other an inch. By training together they eventually come to become friends, and by becoming friends come to realise that there is, indeed, a very thin line between love and hate.

The Bottom Line: This is the type of movie that one can watch over and over again without ever getting tired of it. Kelly and Sweeney are unforgettable in their roles as two people butting heads. It’ll make you smile, make you laugh, and maybe even make you cry. If you haven’t seen this film, yet, you are missing out on what could potentially become your favourite romance movie of all time.

3. WHEN HARRY MET SALLY

Starring: Billy Crystal, Meg Ryan, Carrie Fisher, Bruno Kirby

Director: Rob Reiner

Writer: Nora Ephron

Circa 1989

Hermione’s Rating: 4.5 stars

Who doesn’t remember this movie with fond memories? Whether it be the question of whether “guys and girls can ever really be friends” or the famous orgasm scene, there isn’t one ounce of this film that isn’t worth watching and awing over.

Harry Burns (Crystal) and Sally Albright (Ryan) meet several times over the course of their lives, each time hating each other a little bit more than the last until finally they become friends. When Harry Met Sally is the story of two strangers becoming friends becoming lovers becoming strangers becoming a couple. That’s really all there is to it.

The Bottom Line: Just see it if you haven’t already, and see it again if you have.

2. A&E’S PRIDE AND PREJUDICE

Starring: Colin Firth, Jennifer Ehle, Allison Steadman, Benjamin Withrow

Director: Simon Langston

Writer: Andrew Davies (based on the novel by Jane Austen)

Circa 1995

Hermione’s Rating: 4.5 stars

What better romance story than one that has been written long before Valentine’s (a.k.a. Devil’s) Day was ever celebrated? It doesn’t matter whether or not you read the book; this movie version provides the perfect visual to Austen’s prose.

Set in 19th Century England, this is the story of the Bennett sisters who, out in society, must find themselves their perfect suitors. Second oldest Elizabeth Bennett (Ehle) is by far the most headstrong of the five sisters and when she meets Mr. Fitzwilliam Darcy (Firth) at a social gathering, she finds him judgmental and proud (a.k.a. snobby). Appearances can often deceive, however, but is Elizabeth too stubborn to admit it?

The Bottom Line: This is a long movie, clocking in at just below six hours in length. If you’ve seen it before and decide to rent it, then I suggest watching just the second of the two tapes/DVDs; that’s where all the action starts, anyway. The film is by far the best rendition of the novel so far, and why not when Colin Firth is at the helm? There’s a reason Bridget Jones’ Diary author Helen Fielding dubbed her literary hero Mr. Darcy, and an even greater reason why Firth reprised his role, in sorts, as Mark Darcy in that film.

1. DIRTY DANCING

Starring: Patrick Swayze, Jennifer Grey, Jerry Orbach, Jane Brucker

Director: Emile Ardolino

Writer: Eleanor Bergstein

Circa 1987

Hermione’s Rating: 4.0 stars

Here we have it, folks; the top Valentine’s Day movie of all time. Why, you may ask? For the soul reason that I’ve seen this move upwards of sixty times and have yet to get tired of it.

Baby Houseman (Grey) is off to Kellerman’s, a kind of hosh-posh country club slash hotel with her doctor father, socialite mother, and melodramatic beauty queen sister for the summer. There, she meets Johnny Castle (Swayze), dance instructor and rebel extraordinaire. When Johnny’s dancing partner Penny (Cynthia Rhodes) becomes ill (she gets knocked-up by a sleazeball waiter), Baby valiantly offers to take her place at a dance show at a nearby hotel, guaranteeing that Penny and Johnny will have a job there the next summer.

Needing to learn the moves, Johnny decides to teach Baby a thing or two about dancing…and about life. Conflict abounds, however, when Baby’s father learns of her affiliation with Johnny, but not before the two fall in love.

The Bottom Line: This is one of those movies that you sit through because the last ten minutes are such a great payoff. Indeed, that final dance scene between Swayze and Grey is smouldering…and who couldn’t resist a guy who kisses the tip of your nose in front of the crowd?

Well, gals, that’s the selection. Whatever you decide to do for Devil’s Day, this year, I personally wish you all the best. I myself have a very hot date…with my couch…and my best friends. Here’s to single (though not necessarily bitter) women everywhere!


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