Roy Story

How to Lose a Guy in 10 Days- Does It Still Hold Up in 2026?

Yesterday was my maiden voyage into the Letterboxd list: Movies everyone should watch at least once during their lifetime. It has been a hell of a week and I was wanting to start with something light and fun that I wouldn’t need to emotionally recover from after watching- so after some scrolling of the list I came across “How to Lose a Guy in 10 Days”. I had originally seen the movie a few years back and remembered having a good time, so this 2003 rom com was the perfect pick to kick things off- but does it still hold up? Short answer: mostly yes, let's get into it. image Image via Paramount Pictures

So Benjamin Barry (Mathew McConaughey) is an advertising exec trying to land a large diamond seller, he’s in competition with two women at his firm. But he’s a man who only ever does beer and sports campaigns so they make a bet with McConaughey that if he can get a woman to fall in love with him in 10 days (before the big diamond launch party) then he can have the account. Because if he can get a woman to fall in love with him, he can for sure get other women to fall in love with diamonds, right? (It makes sense if you don’t think about it too much). The woman in question? Well, none other than Miss Andie Anderson (Kate Hudson) the “How To” writer for Composer Magazine, the fastest growing woman’s magazine in America right now. Her current pitch? “How to Lose a Guy in 10 Days”. She comes up with this after one of her gal pals is telling her about how she is doing all these “crazy” things with new guys she’s dating. Andie pitches it as a “what not to do” in a new relationship. If she writes this piece than she can finally start writing more of what she actually wants to write: politics, war, world relations, etc. Who will come out on top, what’s going to win out- career or love?

A few thoughts I had while watching the movie:

-Firstly: Kathryn Hann?!? What are you doing here girl, I forgot you were in this.

-Everything from the opening credits to the sets to the costuming (I kind of forgot about Burberry) were so early 2000s in the best way. Bright colors, fun designs, very whimsy.

-I have memories of playing Bullshit with my family and it went down just like it did in the movie, made me feel nostalgic.

-I clocked that Kate’s hair looked a little off at the beginning of the movie when it was straightened. I loved the progression through the movie where when she slowly starts to become herself, her hair becomes increasingly curly. It was a good way to show her true colors.

-I would give my first born to look as good in any outfit I own as Kate Hudson looked it that Iconic backless yellow dress. And when she put on the Canary diamond the size of a child’s fist? I mean come on… It should be illegal to look THAT good. image Image via Paramount Pictures

#SPOILERS AHEAD If my amazing prose about the movie so far has made you want to watch it- go do it then come back and finish this! image Image via Paramount Pictures

If it is a surprise to anyone the two hot people ended up together, I know- can you believe? It’s not very believable because when you think about it, Andie was acting “crazy” for the first 5-6ish days. And I’m pretty sure Ben never even saw her apartment? I’m guessing that it was due to budget constraints but for the plot: girl could have been a literal hoarder, and he would have never known. I’m just saying, if I was chasing someone down on a motorcycle to give me a second chance, I would like to see how they live, you know?

I did not love that it relied so heavily on gender stereotypes (“crazy” women who get too emotional and attached too fast, and “manly” men who can’t be disturbed during their poker nights by their women or healthy snacks.) Honestly the script really relied on the typical romcom tropes and was pretty predictable. But that is how most rom coms go so it’s par for the course really.

I will say, even though it was extremely predictable, Hudson and McConaughey’s chemistry was electric and really made up for a lot of the show’s downfalls. I had already seen the movie years ago but I was still rooting for them as I was watching last night because they are both gorgeous and deep down they both seem like good people. Yes, I am casually forgetting about the whole dual deceit they were both working on each other, and yes, I stand by my comment.

Overall opinion? This movie was a good time. Not too deep, not too sappy- but just the perfect amount of early 2000s goofiness that you can have a few laughs at and not take it too seriously. Andie was out here in NYC writing at a fun magazine, looking cute, sipping Cosmos on the roof of her apartment, and being swept off her feet with a cutie on a motorcycle? She was really just living my dream now that I’m thinking about it…I’m not jealous at all. But this movie got it’s happy ending and if there is one take way I had it is probably that my anxiety it warranted sometimes because If I was ever on the receiving side of a scenario like someone writing a column about me, I would literally never date again- sometimes it’s good to question people's real intentions. Especially if you’ve been going out for 5 days and they already bought a dog and are referring to them as your joint child. Some dread is helpful… just saying.