All My Complaints About "How To Lose A Guy In 10 Days"

Yes, it's one of my favorite romcoms. But I have NOTES.

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For a while now, my husband and I have had a tradition that we spend Valentine’s Day in and watch a romcom, usually accompanied by some charcuterie and cheese, maybe champagne. We do our “real” Valentine’s Day date night a week early to avoid the rush and crowds and better secure a good reservation at our first-choice restaurant. Two years ago, we watched Hitch (2005). Last year, we watched When Harry Met Sally (1989) on V-Day, and this year, we watched How To Lose a Guy in 10 Days (2003).

Most of you probably know How To Lose a Guy in 10 Days, but for those of you who don’t, it stars Kate Hudson as a magazine article writer named Andi Anderson, in a sort of double-crossing romance ruse with Matthew McConaughey, who plays an advertising executive. Congratulations to screenwriters for coming up with two non-novelist jobs, although I’m going to deduct points for one character still being a writer. Thank goodness neither of them worked at an “art gallery.”

Anyway, the aforementioned ruse is this: Andi suggests that for her “how-to” column (she works for a Cosmopolitan-inspired magazine) she will date a man and then purposefully drive him away within ten days as sort of a reverse-how-to. Her target: Benjamin. Meanwhile, Benjamin is the subject of his own much less plausible scheme involving his own career. To secure the pitch for the coveted DeLauer diamond company, he must check notes prove he can make a woman fall in love with him by the night of the big DeLauer diamond-themed promo event. Sounds legit.

I watched this movie for the first time when it actually came out, and in hindsight I probably envisioned my future workplaces looking a bit like this—all fun and games, everyone gossiping, various ruses and gambits and bets being made all the time, coworkers all up in each other’s personal business (in a fun way) and everyone dressed in cute little pencil skirts and floral chiffon skirts. Well, then the real world happened and I just worked with a bunch of male engineers in hoodies and then got fired over and over again. Anyway!

So, I still love this movie as much as I always have. But watching it in 2026 brought up some interesting observations.

First of all, as I just mentioned, Benjamin’s gambit is absolutely ridiculous. Andi’s is completely plausible—she works at a women’s magazine and covers dating, so yes, of course it makes sense that she might date a guy for the purpose of an article. But as a former “advertising executive” (okay, I was an account executive which is actually just entry-level, but bear with me) there is no way that anyone would secure a pitch by proving they could make a woman fall in love with them. Still a good movie, and I will suspend some disbelief, because this was clearly something that needed to happen for the plot.

Another observation: Kate Hudson is just extremely young in this. I watched it when I was thirteen, so both actors just seemed old to me. Matthew McConaughey seemed about forty, and I assumed Kate Hudson was in her early thirties. Both of them were essentially Prince fucking Phillip to me. But no! As I started watching it again at the ripe age of thirty-six, I noticed she looked way younger than I am now, and at first I thought, Well, maybe she just has one of those faces but then I looked her up and it turns out she was twenty-three at filming. Her two work-wives are played by actresses who were twenty-seven and twenty-nine at filming.

I’m not the first to notice this—other people pointed out that Andi Anderson had a Master’s degree, not to mention her own column in a major magazine, which makes it a little weird for her to be in her early twenties. But my theory is that she was just playing older. Meanwhile, Matthew McConaughey was also younger than I imagined at the time of filming. He wasn’t forty; he was in his early thirties. My best guess is that they are supposed to be about 5-7 years apart. I think he’s playing roughly 33-35, and she’s playing late twenties.

I don’t think this age gap (even if it was meant to be ten years) is a problem at all, although I do think if they were truly playing a couple with a ten-year age gap, it would at least have been mentioned somewhere. Perhaps even in a positive light! But I think what irks me is that they’re more or less pretending to be age-peers, when they’re obviously not. I also had this issue with When Harry met Sally, where the actors are fourteen years apart but explicitly playing people the “same age.”

And now, my biggest gripe with this movie, and the only gripe that actually bothered me was that Andi Anderson’s rigid and difficult boss (played by bebe Neuwirth) was actually right about everything.

Side note: her boss’s name is Lana, but I just looked it up and her full name is “Lana Jong.” The actress who plays her is definitely not Asian, but sports pale powdered makeup, red lipstick, a short black bob, and various silk Y2K Chinese-inspired silk dresses. Not to be the Friend Who’s Too Woke, but…what exactly is going on?

Another “just Asian enough for you to be asking questions but generic enough for plausible deniability” top:

Of course, “Jong” can be a Northern European last name, but combined with all the other things, it’s just…a little weird. She’s getting a little too Chinese with it, and this clearly wouldn’t have flown in 2017. Also, there are Asian actors in the movie, so like…they could have found one if they wanted to. Anyway, moving on.

Re: “Lana Jong” (if that is her real name) there is a work subplot that ties in nicely to Andi Anderson’s story—Andi works for a vapid women’s magazine that covers mindless topics like fashion, beauty and dating. But she really wants to write about more serious, intellectual topics, like, in her words, “politics, economics and poverty.” (It’s like someone Googled “what would a serious journalist write about?” Sorry, no—it was 2003. They used AskJeeves.) Hence her Master’s Degree. There is a second gambit tied up in her “How To Lose a Guy” article which is that if she publishes this project, she can write about “anything” she wants, per Lana’s promise.

But after the article comes out, even though Lana loves it, she doesn’t get to write about anything she wants. Well, she can. It just doesn’t have to be a how-to column—it can be about shoes, makeup, laser treatments, anything.

At this point, Andi realizes she’s been had, and quits her job. And like, fine, it was probably a bad fit. But aside from being misleading (or in the worst case, a bit dishonest) Lana did nothing wrong! Well, aside from the blatant cultural appropriation, but it’s not my job to educate you.

In one of the earliest scenes between the magazine writers, Andi, who was explicitly hired to do how-to columns, announces she’s working on something “a little different” and then says she’s writing a “political piece.” Girl, what? I know writers can only write about writers, but surely a writer would know how ridiculous this was! She wasn’t hired to write about politics! It’s not that Lana is just too ditzy to care about politics—she’s running a beauty and fashion magazine! Why the hell would Andi’s “political piece” fit in? Lana immediately nixes the idea, which was obviously correct. FOH with that bullshit.

For the whole movie, we’re supposed to see Lana as kind of a phony and difficult person, but she’s literally just doing her job and Andi is being a real primadonna, trying to shoehorn her crusty ass articles about economics into Cosmopolitan. It’s ultimately good that Andi tries to get a job elsewhere, but I had a very hard time siding with her.

Given that I’ve been a bit of a hater, I have to give it credit where it’s due: first of all, it’s just a funny movie and the humor really holds up so many years later, even if some of it is a bit over-the-top. Second, I really love the fashion, especially the choice to put Kate Hudson in multiple slinky low-back dresses:

Anyway, this was a good movie. I’m still glad I re-watched it, and I am officially obsessed with sewing a dupe of Andi’s iconic yellow formal dress (to wear where? The UPS store? TBD!) But I couldn’t very well let this movie slide without defending Lana Jong (whichever ethnicity she may be).