Fact: How To Lose A Guy In 10 days is one of the best romantic comedies of all-time. It’s stood the test of time and is on constant rotation (in my house, at least). From the iconic Y2K fashion and delightfully convoluted plot to the undeniable chemistry of a young Kate Hudson and Matthew McConaughey, it has all the key ingredients of a classic rom-com.
Eagle eyed viewers know that Kate Hudson embodies the perfect early 2000s heroine: she lives in NYC, has a glamorous job, is shockingly gorgeous, yet somehow so relatably clumsy. As a fellow NYC media girly, I selfishly love this trope — but not all films within the genre are created equally. And while I absolutely adore this film, not every aspect of How To Lose A Guy In 10 Days holds up. Let's dissect the movie's most iconic moments together because I...have questions.
Andie doesn't seem to understand how magazines work.
The movie opens with our charismatic heroine finishing up an article on “bringing peace to Tajikistan.” It’s clearly well-thought out and in-depth, but she forgot two crucial steps: pitch it to her editor and get the actual assignment!
“It’s brilliant, it’s really moving” says her coworker Jeannie, who has clearly not read the article. “But it’s never going appear in Composure magazine.”
So at least one of these writers has actually read the magazine’s mission statement. But this scene begs the question - why doesn’t Andie know how newsrooms work, let alone the type of articles her publisher is actually looking for?
Composure is a relic of a forgotten time in media.
Composure sounds like your typical mid-aughts women’s glossy, like Glamour or Lucky. I wouldn’t be surprised if they’re part of a large magazine conglomerate, like Condé Nast or Hearst, with multiple different titles. If this is the case, why didn’t our Andie just freelance for another title? Or consider putting in for a transfer?
Andie's boss is actually cool!
Her boss, Lana, is pretty cool. She begins the regular team meeting with shoes off and deep breathes — this is my kind of meeting! Miranda Priestly could never!
Does Andie really care about Tajikistan?
“I want to write about things that matter! Politics, religion, foreign affairs, things I’m interested in!” Andie whines to Jeannie, who does an excellent job pretending to care. However, is seems like Andie might be pretending as well, as she fails to mention any of these interests ever again throughout the duration of the movie. Not to mention, Kate Hudson doesn’t really seem to be buying that line herself. I could see her writing about sports, maybe?
NYC traffic is no match for Andie IRL.
It's 30 minutes to the staff meeting, and Michelle (work BFF #2) isn’t there yet. Logically, there is no way they’re getting to her apartment, cleaning her up, giving her a pep talk, and getting back to the office in time for this meeting, and in rush hour traffic. Yet somehow...Andie Anderson prevails? I don't think so!
Living in NYC was never THAT affordable.
Circling back to Michelle's apartment...all I can think about when I see where all these women live is: How do all these single girls live alone on junior magazine salaries?!
Andie should lean on her media connections more, TBH.
After Andie retrieves Michelle, we see them getting out of the taxi in Times Square. Realistically, they’re pulling up to 4 Times Square — AKA Condé Nast’s previous home. Which proves our theory correct: Composure is part of Conde, a media giant with 50+ other titles, which means she could have easily asked her editor for an intro elsewhere to start freelancing and writing about the things she pretends to care about..
Also, Andie's constantly flirting with an editor from Sports Illustrated. She’s clearly well-connected within the media world, so why not ask this man about freelance opportunities? Someone who's shouting about NBA finals — completely unprovoked — would do well writing about sports, a subject which she seems to actually be interested in.
What IS the deal with Sports Illustrated guy, anyway?
A hot and successful guy gives Andie a pair of buzzy NBA tickets and she chooses to bring her coworker who hates sports?! I think Andie is missing the memo, but this at least explains why she's single at the start of the movie.
The "Cool Girl" trope is soooooo tired.
Judging by how she LOVES sports, eats meat, and doesn't experience girly things (like feelings!), it's clear that Andie was written as the cool-girl and anti-girly girl. Remember that trope?! I’d want to hate her, but Kate Hudson is honestly too charming in this role.
Someone is probably missing that green cashmere sweater.
Since Andie is the world's best friend (and coworker!), she casually steals a cashmere sweater from a passing rack. I'm pretty sure someone will miss that during the run through, and I feel for the assistant who get blamed. However, Katheryn Hahn does look amazing in this shade of green, so I guess it's worth all the drama, drama, drama.
Drama, drama, drama is an eye-roll inducing refrain.
I'm not sure who thought this was a clever, punchy line, but it's grating. And Jeannie — who's otherwise cool and relatively smart — keeps repeating it throughout the film.
Michelle doesn't seem like a very committed journalist...
Michelle comes to the meeting unprepared and still teary-eyed. She tells her editor-in-chief that it’s because she got dumped (Lol!). Her boss briefly sympathizes, tells her she looks fabulous, and gives her an out - write about it! Yet, Michelle declines. How does this girl still have a job?! She would definitely not have survived the ’08 recession and media cuts.
Andie's frustration is totally preventable!
Andie finally pitches her article to Lana during the staff meeting, which takes place after she has already finished work on it. You can see her boss’s face drop when and says “it’s something different, a political piece.” Lana then reminds Andie that what they cover is: “Fashions, trends, diets, cosmetic surgery, salacious gossip — that’s Composure.” From her tone, I get the feeling that Andie has heard this before.
Ben's intro is heteronormative AF, and extremely of the times.
In case you missed it, Ben is cool. He is a manly man who wears leather (!) and rides a motorcycle (!!). Not even rush hour traffic can get him down!
Ben’s friends are incredibly lame.
Ben is the alpha male of the office and clearly loves it. The basement dwellers he spends his time with exist only to make himself feel good and look better in comparison.
Why does Ben have a southern accent if he’s from Staten Island?
The origin of this accent is one of the greatest mysteries of all time. Also, does Andie have any family at all?
The titular pitch is equal parts cute and cringe.
Andie pitches Michelle's love life as a "what not to do" story, which is a cute idea in theory. But then she continues, “I’ll be everything guys hate: Clingy, needy, touchy feely.” This is such pick-me behavior! Ugh.
The type of bar they go to does not exist IRL.
Now on a mission, the girls go to a bar which is known for being frequented by successful men with good jobs. It's essentially an IRL version of The League.
Ben's "business" meeting is awkward and non-sensical.
Why did Ben, the Judy’s, and their boss have to relocate to this trendy bar just for this meeting? I don't understand why they couldn't just book a conference room at the office.
While the setting is strange, it's not nearly as odd as the conversation: “A woman in lust wants chocolate, a woman in love wants diamonds.” This is a weird generalization, but I find myself feeling happy to live in a world where we can buy our own diamonds.
Kate Hudson has a great smile, and everyone knows it.
While picking the girl for Ben, Judy points to Andie and says: “Her — with the blonde hair, grey dress, pretty smile.” We get it, she has a nice smile, but they’re really going overboard as Andie is grinning like there's no tomorrow. I need to know what she's laughing at because it seems HYSTERICAL.
The plot of this movie is convoluted AF
We already know this, but I just can’t get over this line from Ben’s boss: “If you come to this party with a woman who’s really in love with you, you can make the pitch to the DeLauers.” Like, why would that matter to his boss? Are we just suspending belief that Matt is insanely hot and any woman wouldn’t fall for him?? Were bosses in the 2000s really that involved in their employees personal affairs, or was there just nothing on TV??? So many questions!!!
Alliteration means it's a love match.
Andie Anderson meets Benjamin Barry. The 2000s really were a simpler time.
Andie and Ben's first date is weird
Andie shares that she has a master’s in journalism from Columbia, explaining that “if I do it right, I can write about whatever I want!” To which Ben asks, “What’s that, shoes?” And we watch Andie sheepishly smile while she struggles to remember her interest in politics and the environment.
Ben changes the topic and tells her, “You can ask me three questions.” Why only three, Ben? They literally just met, and that’s pretty weird.
Awkwardness aside, that lobster looks really good.
Meeting the parents brings more questions than answers...
Katheryn Hahn playing shrink is one of my favorite moments, especially when she sends Andie to Staten Island (the horror!). Here, we see that no one in Ben's lovely family shares his accent, which makes me wonder if he's been using fake dialects his whole life and his family has just learned not to question it.
Hooking up in your childhood bathroom is not sexy!
Andie and Ben also have sex at his parents house...in the shower during the middle of the day. They weren't even trying to hide it!
Andie's post-sex hair is impossibly stunning
Emphasis on impossible, because our girl didn't bring any hair products for that day trip. But I'm willing to look the other way since she's absolutely glowing, thanks to Relaxed Rom-Com Girl Hair ™️!
Andie's yellow dress holds up all these years later!
We've said it before, and we'll say it again: butter yellow looks good on everyone.
Kate Hudson does a great job singing badly!
Andie is a terrible singer, but Glee fans have known for years that Kate Hudson is not. It makes me happy knowing that we now have a full album for songs from THE Andie Anderson.
The ending is a cute disappointment...
Ben's motorcycle chase to catch up with Andie is iconic, but she left a big opportunity (supposedly her dream job!) to stay in NYC with Ben. I guess Andie's journalism dreams can't compare to being unemployed with a boyfriend?
"The girl leaving it all behind for her guy" is one of my biggest gripes with early aughts rom-coms. I'm sure there are generic marketing agencies in DC that Ben could have transferred to, and let Andie pursue her dream, but I guess our beautiful leads didn't consider that option.
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Header image via Paramount Pictures
