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My Favourite Rom-Com: How to Lose a Guy in 10 Days

Why How to Lose a Guy in 10 Days is the perfect nostalgic rom-com to watch this Valentine’s Day…

Shown: (l to r) Matthew McConaughey as Benjamin Barry and Kate Hudson as Andie Anderson
How to Lose a Guy in 10 Days (2003).

This Valentine’s Day, most of us are unable to celebrate with the ones we love due to Coronavirus-restrictions, however, we can choose to indulge in some cheesy romantic-comedies to celebrate the occasion. What 90s and early 2000s rom-coms satisfy within me is a return to innocence. They make me feel warm and nostalgic and give me space to put my brain on ice for an hour and a half while I watch extremely good-looking people play out extremely predictable storylines. They are the filmic equivalent of a nice hot bath on a Sunday evening. 

As my anxiety grew as a teen, I would find myself seeking out every rom-com I could find and consume; a great escape from whatever sadness I was wallowing in. They represented a problem which could be solved within the space of 90 minutes. They were a brief, romanticised hope of an easy and happy ending. However, my favourite, and one that I still return to, is How to Lose a Guy in 10 Days starring Kate Hudson and Matthew Matthew McConaughey as the romantic leads. 

How to Lose a Guy in 10 Days was released in 2003, in what some have referred to as the ‘Golden Age of Romantic Comedies’. This film was not as widely well-received as I thought it would be. A fact I was not aware of until writing this article – truly, I saw this film as up there with more traditional favourites such as When Harry Met Sally. It holds a mere 42% on rotten tomatoes…. I wondered, is my taste so questionable? Yes! Did that mean the film was that bad? No! 

The plot centres around Andie Anderson*, a journalist working at a Cosmo-esque women’s magazine called Composure. She currently has a column as their resident ‘how to’ girl, but holds ambitions to write about more serious and political issues such as ‘How to Bring Peace to Tajikistan’. Rejected by her editor for these ideas, Andie exploits the pain of her lovesick best friend Michelle (played by the wonderful Katherine Hahn) and propositions an article on – you guessed it – ‘How to Lose a Guy in 10 Days’. In this, she will drive away a potential suitor with common mistakes that women, like Michelle, make which scare men off such as naming their penis (?), buying a dog after a few dates (again, ?) and being too clingy. 

Meanwhile, Benjamin Barry who works as a hot-shot marketing executive makes a bet with colleagues to be in charge of a big diamond campaign; to win said campaign, he bets that he can make any woman fall in love with him in the space of 10 days. The two, of course, meet and decide to use each other – unbeknownst to one another – for mutual gain. However, as with all such rom-com set-ups, Andie and Benjamin fall for eachother in the process.

There are many problematic, unrealistic and nonsensical parts of How to Lose a Guy in 10 Days. For example, the fact that Andie is meant to be 23 in the film. She wants to be a ‘serious’ journalist, yet feels stuck at her job as a staff writer at a women’s magazine. A 23 year old with a master’s degree and her own column in a popular women’s magazine as (presumably) her first job, and she’s out here complaining! Similarly, Andie’s questionable journalistic ethics seem so obvious now; considering she held a journalism master’s degree, her actions were morally ambiguous at best and unethical at worst. Michelle’s portrayal as the hysterical, lovelorn woman is problematic in itself, but Andie’s further exploitation of this pain for a story was too. If that wasn’t bad enough, she then emotionally manipulates (what she thinks is) an unassuming man.

It;s not just Andie’s questionable actions, but Ben’s too – even the whole premise of a man making a ‘bet’ to make a woman fall in love with him seems so dated now (see: She’s All That). However, this was the 2000s and, also, it’s a rom-com, so I don’t want to obsess over the flaws in what is an already-exaggerated and convoluted plot. Rom-coms from this time period are the one place where the plots don’t have to be realistic. These films are not the place for nuanced portrayals of women and their relationships, but they are the place for escapism and fun. 

What makes the film so watchable – and probably why it’s my favourite –  is the two romantic leads. Kate Hudson and Matthew McConaughey shine in their respective roles. Kate Hudson, fresh off the wave of Almost Famous, brings the same warmth and humour that she brought to her role as Penny Lane. She conveys the ridiculous set-up of Andie’s hijinks with great comedic delivery. Matthew McConaughey is also at his most charming and laid-back making him the perfect rom-com lead. His relaxed portrayal of Ben contrasts Andie’s invented high-maintenance. The two actors save the film from being, what could easily be, laborious, sexist slog of a film. Their chemistry is palatable, particularly in the scene where Andie meets Ben’s family on Staten Island. Letting go of her previous facade with Ben, Andie drops the penis nicknames and the ‘love ferns’, and is, finally, herself. The two play Bullshit with his family and go for a motorcycle ride. They return home and have that all-powerful movie-kiss in the bathroom and the scene fades to black. 

These scenes offer probably the best part of the film. Here, the audience are hoping Andie and Ben will forget their plans, drop the charade and ride off into the sunset. But, we are not even into the third act yet! On returning to New York, Andie and Ben attend his work gala in aid of the his company’s diamond campaign. She, whilst looking unreal in that iconic yellow dress, inevitably, finds out that she was part of a bet. Ben, similarly, finds out he was an experiment for her how-to column. Both seem to try and exert some sort of moral high-ground over the other and we are treated to the culmination of this as they sing the iconic, angry and drunken rendition of You’re So Vain.

Obviously, this isn’t the end of Andie and Ben. Andie decides to leave New York and pursue that ‘serious’ journalism career she’s been banging on about the whole film. When Ben finds out he chases her taxi across the Manhattan Bridge, riding his motorcycle alongside the car to stop her from leaving. She, of course, puts her morals on hold again and decides to stay. This scene draws on so many rom-com tropes that came before it, giving us the predictable and familiar satisfaction that we all know and love. Cue final kiss. 

How to Lose a Guy in 10 Days gets the fine balance between romance and comedy right. Where some rom-coms lean too far into one or the other, How to Lose a Guy, never lets one element overshine the other. As mentioned though, this is probably not so much to do with the writing, but because of the warmth and comedic timing of the actors. 

Even if some rom-coms are justifiably bad, they provide solace and fantasy. They’re a tonic for reality, and How to Lose a Guy in 10 Days is no different. No one’s watching rom-coms for their realism, but How to Lose a Guy is light and easy enough to make you believe in love again. This Valentine’s Day, indulge in watching your favourite rom-com, even if it is just to laugh at its lack of integrity or datedness and, for 90 minutes, slip into a perfect, nostalgic world where COVID-19 doesn’t exist yet and we could touch the ones we love – even kiss! 

And if you’re a fan of How to Lose a Guy in 10 Days like me, Kate Hudson and Matthew McConaughey have both actually hinted at a sequel. Although I can’t bear the idea of an attempt to somehow make this set-up feminist and progressive, there’s also been talk of a TV reboot so, you never know… 

* Firstly, lol that her name is Andie Anderson, and secondly, why are all ‘serious’ journalists in 2000s comedies called Andie?! (See: Devil Wears Prada).

Written By

Rochelle is the co-founder of The Culture Sift.

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