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5 Thoughts We Had While Rewatching How to Lose a Guy in 10 Days

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5 Thoughts We Had While Rewatching How to Lose a Guy in 10 Days

Pineapples Don't Have Sleeves

How to Lose a Guy in 10 Days is one of our all-time favorite romantic comedies. Starring the charming Kate Hudson and heartthrob Matthew McConaughey, it’s a classic from the golden 90’s era that has all the elements of a successful rom-com: two people trying to deny their love for each other, supportive friends, and a predictable yet satisfying ending. Bonus fact: the movie is based on a best-selling book with the same name, but the characters were created specifically for the film. Can you even imagine the movie without Hudson and McConaughey’s electric chemistry? Yeah, neither can we.

We have to admit that we have probably seen this movie more times than we can count, but this time around, we decided to approach the movie a little differently. How does it feel watching this movie classic now? Are there any moments that make us cringe, or are there stereotypes being perpetuated that we know are not only sexist, but unnecessary in 2023? Here are our thoughts:

The Cool Girls only exist in men’s minds

Let’s compare the two main female characters, Michelle and Andy, to make a point. Michelle, played by the amazing Kathryn Hahn, is the “uncool,” clingy, and needy best friend. Andy, on the other hand, is the sports-loving, effortlessly beautiful, and super confident writer. 

In the movie, Michelle tells Andy that “she could barf all over a man and he’d say, ‘do it again!’,” while Michelle is constantly crying over her ex, Mike, who she supposedly ruined everything with by being too emotional. So, we can’t help but wonder, is Andy the all time male fantasy?

But seriously, are we still expected to act likable for men? Can't we just be ourselves and hope that the right person will stick around no matter what?

Michelle may be an exaggeration, but she represents an idea that many of us grew up with: if you want men to like you, you have to have shared interests, act cool, and be unemotional. Newsflash: a relationship that starts this way is doomed to fail. Who cares about being cool? Be yourself, be emotional if you feel like it, and don’t be afraid to say “I need you” and be vulnerable. And for the love of all things holy, can we stop dating assholes already?

The Stereotypes of the Fashion World

We’re the first ones to admit that there are parts of the fashion world that can be problematic. But it’s frustrating to see that talking about fashion and girl issues are shallow but talking about sports is cool and edgy. Are we really still stuck on the idea that women only care about gossip, body diets, and clothes? And even if we do, that doesn’t mean we don’t care about politics or climate change. It’s annoying to see Andy’s boss constantly telling her that she can only write about dating advice and shoes, when in reality, we all know that women are much more complex than that.

In the 90's, there was a clear trend of portraying female tastes as dumb and superficial, while male magazines were cool and trendy.

It’s taken us a while to realize that liking fashion isn’t a guilty pleasure; it can be as simple or complex as you want it to be, and there’s nothing to be ashamed of if you want to talk about “girl issues.”

When we started our blog, #GirlsTalk, we wanted to create a safe space for women to talk about anything: movies, dating problems, fashion trends, politics, sustainability and quotes to live by.

Let's make 2023 the year where guilty pleasures become things to be proud of!

Is patience the key to a good relationship?


Yes, we might be overthinking this whole issue, but stick with us, we have a fair point. Andy and Benjamin stayed together because of their own personal bets but sticking through the hard times made them leave their differences aside and allow them to see parts of each other they might have never seen.

So, are we closing doors too soon and losing what could have been good relationships?

We clearly are not telling you to stick around no matter what, no one has time for drama and unnecessary issues, but as Michelle Obama would say: Patience and sticking through the hard times is what allowed her to have 30 plus years of happiness with Obama. Can you remember a relationship where you might feel you jumped to conclusions too soon and never gave the other person a moment to explain? It’s definitely a trend of the 21st century, seeing relationships as disposable and not seeing the values after challenges.

Think about your own personal life or work throughout your whole life, almost everybody will tell you that sticking around through the hard times is what will make you stronger; that everything that goes up eventually comes back down; that if you work really hard for it, even if at the beginning is challenging, it will be worth it…So, are we giving relationships the same treatment or are we used to saying NO too fast?

Yes, in the movie they clearly had two specific interests but love only prevailed when they learned from the drama and tried to see the bigger picture. Are we taking dating advice from How To Lose a Guy in 10 Days? In a way, yes we are!

Being yourself is the new cool

You might have missed this detail, but it says a lot. When Andy is pretending to be annoying, her hair is straight, but when she’s herself, it’s curly. Coincidence? We didn’t think so either. We’re a sucker for romantic comedies, but we now understand that we have to see them with different lenses because most of the time, their reality is far from the truth. 

No, you don’t need a slow motion shot of your incredible beach bod, or have to laugh about every uncomfortable joke, wear makeup in the morning or dress sexy everytime…even less if it is for somebody else. The right person will stick around and see beauty in the moments where you’re being your true chill self, 

What is the sexiest thing about a woman? Being her true confident self.

Let’s think about Michelle in the movie, all her friends are reminding her all the time that she is basically a dating red flag, but at the end, Mike comes back, no? Why are we always preaching the strategist and cool Andy, instead of appreciating how relieving it is to meet someone like Michelle, a person who you know what you get from the beginning with no games played. Isn’t that refreshing?

Let’s stop selling ourselves as these goddesses who have no feelings, don’t go through periods or have emotional moments. We’re all those things and guess what? That’s exactly the reason why WE’RE GODDESSES.

Meeting the family is the end of the hunger games

How To Lose a Guy in 10 Days shows this perfectly when Andy and Benjamin start changing and letting their walls come down after meeting Benjamin’s family. But this is far from the first time family played an important changing role in a relationship or movie, we have a few more examples where you see this: from the always fun “Crazy, Stupid, Love”, the iconic “Crazy Rich Asians”, and one of our all time favorites, “The Big Sick” (inspired by a true story, if you haven’t seen it, do yourself a favor, and go watch this cinema jewel). 

Family, family, family…for better or for worse, it’s the catalyst relationships sometimes need

 to demonstrate a long-term commitment, show an important part of your life, shake things up, or show what life is like in “the real world”. In some cases, it can even reveal a part of yourself that you may not have been comfortable sharing before. Regardless of the reason, family always reveals the true essence of who you are, the part of you that you can never run from.

So yes, you can play all you want the games and bets as Benjamin and Andy do, but in the end, the real world will be waiting and will always be the reason a true relationship makes it to the next step or fails completely.

Don’t get us wrong, the film has some conflicting parts but it also brings that 90’s nostalgia that we’re craving so much. So, go watch it again and enjoy the good and bad dating advice of How To Lose a Guy in 10 Days. Happy watching!

Pineapples Don't Have Sleeves

I want to officially introduce myself, I’m Pineapples Don’t Have Sleeves and I was born 6 years ago from the creative mind of a Colombian woman called Johanna Nodier who studied in Milan and Paris. We share our love for pineapples, wearing colors and dreaming with fantastical printed dresses. I’m a cosmopolita, yes baby, I’ve been to Milan, Bogotá, Aruba and Colombiamoda Fashion Week. I have always stood for women being whoever they want to be and breaking the rules of fashion. It’s so nice to meet you and welcome to my world!

Thank you for reading this article and being part of #GirlsTalk, cheers for learning and growing together!

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