Before Jenna Rink and Andy Sachs could pen a single column inch, How to Lose a Guy in 10 Days’ Andie Anderson (Kate Hudson) was the rom-com genre’s senior editorial correspondent. As the “How to” girl of the Cosmopolitan stand-in Composure magazine, the quirky, blond spitfire would serve up ways to get out of parking tickets or give better blowjobs in her advice column. But she wanted to be taken seriously. Andie wanted to write about politics and religion instead of Botox and whether or not blonds really do have more fun. One particular assignment, she was led to believe, would help her do that: making a guy fall in love with her, and then scaring him off in just 10 days. Her mark? Charming ad exec Benjamin Barry (Matthew McConaughey), also plotting to make Andie fall in love with him in the same timeframe in order to land a diamond campaign at work. 

Andie does her best to repel Ben through such tactics as a strange-looking dog dressed in Burberry, a photoshopped album of what their children would look like, and a “love fern” that he needs to keep alive, while Ben attempts to woo Andie with cherry-glazed lamb and a jaunt to Staten Island to play Bullshit with his family. Far from a practical guide to love, this became the recipe for one of the most memorable rom-coms of the early aughts: How to Lose a Guy in 10 Days.

Released in February 2003, the Donald Petrie–directed film received mixed reviews. Hudson and McConaughey were charming, critics said, but the film was written off by some as too predictable. It didn’t matter—it became a box office hit and delivered a chemistry pairing for the ages. But over the years, How to Lose a Guy in 10 Days has been remembered much more fondly—as a thrilling rom-com with feminist subtext that leans into its absurdity and cleverly plays with the trope of a “crazy,” “clingy” girlfriend.

In honor of the film’s 20th anniversary, Vanity Fair looks back on why we’re still so obsessed with How to Lose a Guy in 10 Days after all these years.

The concept for How to Lose a Guy in 10 Days originated from a novelty humor book featuring stick figures, written by Michele Alexander and Jeannie Long. 

Lynda Obst (Producer): Christine Peters had bought a stick-figure book that I think her assistant had found in New York. It [had advice like], “Don’t wear mandals,” and things like that.

Donald Petrie (Director): It’s almost like a children’s book. It’s a stocking stuffer for Christmas. 

Christine Peters (Producer): It’s basically 20 Xerox pages. These two writers, the next day after one of their nights of partying, said, “how do we lose a guy in 10 days, let’s write down all the crazy stuff.” One girl did the stick figures and the other one was writing “the days.” “Let’s first name his penis, let’s meet him at a party, let’s tell him he reminds us of our father.” Everything every guy doesn’t ever want to know. 

Kristen Buckley (Writer): I always tried to find a kind of different way in. I didn't want to make a female character the brunt of a joke, so I was pleased when it came to me to have it be like, [Andie is driving him away] deliberately. 

Obst: What really drew me to it was this gender sense of humor—this perspective on how men expect women to behave and what women do that drive men out of their minds. It seemed really juicy, so I began developing scripts.

Buckley: This was a little bit after There’s Something About Mary, so, earlier drafts were a little bit raunchier and crazier. 

Following the success of Almost Famous, Kate Hudson was eyed to lead How to Lose a Guy in 10 Days. There was a lot of back-and-forth over who the leading man would be.

Obst: There was an agent at CAA who actually represented Gwyneth Paltrow at the time—his name is David Lonner—and we were having a fun lunch, and he said, “Oh, you would love this project that Gwyneth is thinking of getting involved with. It’s at Paramount and there’s no script yet.” I was like, “Oh, well, I’m at Paramount, and I like Gwyneth.” So then I called my studio and I said, “There’s something called this, How to Lose a Guy in 10 Days. It really sounds fun.” 

Burr Steers (Writer): Initially Gwyneth was attached to it, and then at some point, she must have had a conflict and had to pull out. 

Obst: At some point, [former Paramount president] Sherry Lansing and I, were both madly in love with [Kate Hudson]. It’s clearly after Almost Famous. I just remember, we turned to each other like, “This has to be Kate. She’s hilarious.” And so Kate got attached. 

Kathryn Hahn (Actor/Michelle): I remember Kate was so fucking normal for a person that grew up in fame. I was so moved by what family meant to her and how dearly her parents instilled that in her. She, Annie Parisse, and I became fast friends and made a lot of dumb trouble, smoking, hanging out, and just laughing all the fricking time. We, one late Friday night, were inspired to drive to Kate’s family’s lake house for the weekend. Kate asked me to put my bathing suit on and I came down and she said, “Honey put on your suit,” and I said, “This is my suit.” I don’t think she had seen a tankini before. 

Kate Hudson (Actor/Andie Anderson): We were looking at guys and kept going back and forth about who would be the right guy. The guy for me was really important. Matthew came up in a meeting and I thought that was a great idea. I loved his energy. We immediately just got along. 

Obst: I’m on the phone with Jim Osborne, who was then at CAA, and he says, “What about Matthew McConaughey?” I’m like, “Well, Matthew McConaughey is so Texan, but it’s kind of genius.” So that’s in the back of my head. Now we’re in the meeting and Sherry says to Kate, “We have to bring this to a head. We have to find an actor that we both agree with, and I thought the test was terrific [with Matthew].” Everybody gave their positions. In order to break the impasse, I said, “What about Matthew McConaughey?” And then Sherry said, “Matthew McConaughey.” And Kate said, “Matthew McConaughey.” And John Goldman said, “Matthew McConaughey.” Everybody just looked at each other, and Kate said, “I would do it with him.” 

Matthew McConaughey (Actor/Ben): I remember considering whether I was going to do it or not one night while on a walk down Sunset Boulevard when suddenly, this guy comes up out of nowhere to me—he was a fortune teller guru [and] goes, “Can I tell you your fortune real quick?” I was like, “Yeah, man. Sure.” He immediately goes, “There’s a movie you’re considering right now. It’s a romantic comedy. You have to do this or it will be one of the biggest regrets of your life. It is going to be a blast, it is going to be an incredible experience and it is going to make a bunch of money.” I remember thinking, Did the studio hire this guy? I laughed at the thought, but I also remember taking a more serious consideration. I think I even accepted the offer the next day.

Petrie: I went to the writers and said, “Okay, I gotta have some kind of subtle explanation of why this guy is an advertising exec in Manhattan, and yet he’s got that Texas twang about him.” So we took his father and made him be a Navy guy, so he would have been stationed at different places around the world, and Celia Weston, who came in to play the mom, she is Southern.

The scene where Michelle (Kathryn Hahn) pretends to be a couples therapist was filled with improv from Hudson.

Obst: We were beginning to realize that Kathryn Hahn was a genius. She was really funny. But you know when it starts dawning on you that “Oh, my God, this person is very major.” That’s what happened during the shooting of that scene. She was already carrying the girl company. She and Kate really hit it off and she was just so brilliant at banter, and she was the friend who had been dumped, so she had something to play.

Hahn: I knew I could play “quirky” because at that point that is what Hollywoodland was asking me to do. I was on a show called Crossing Jordan, [and] I was the quirky intake “girl” in the morgue, and later became the quirky grief therapist in the morgue.

McConaughey: This is a classic three-person comedy where two are in on the joke and there’s an “odd man out.” In this case, it was me, Ben. This scene ramped up and came alive immediately. Some of the laughs in the scene are me laughing at how fun it was making the scene. Kathryn, Kate, and I really had fun pushing this one.

Obst: That scene was perfect in almost every way. Everybody was playing off of everyone. Everybody was so confident in their character in that scene that each performance is coming from a very specific direction. And of course, Kathryn, she’s very meta in this scene.

Hahn: The couples therapy scene was so much improv. Kate and the tissue under armpits really got us, [and] my Sally Jessy [Raphael] glasses. 

Petrie: Kate, and that tissue under the armpits, that wasn’t in the script. She just started doing this and the “I sweat when I’m upset” line.

Hudson: That was just ad-libbing, and there’s a ton of fluid improv in that scene.

Hahn: I just kept thinking, Who in the world would ever fall for this? But Matthew kept the scene so grounded by clearly playing along with how batshit it was. We were crying we were laughing so hard. I remember after Donald cut it, he said to me, “There are some cutaways that might not be so flattering of you.” As if I have ever cared. Love him for that.

Andie’s iconic dress, seen on the movie poster as well as in the film, was yellow because of the diamond necklace she wears during the DeLauer gala.

Hudson: [Karen Patch, the costume designer] liked that color of the Isadora—the yellow diamond. So the color was very specific. 

Obst: There was a yellow diamond around the white diamond at the center, we knew that the yellow would set off the jewelry.

Hudson: [Karen] worked with the [Carolina] Herrera team to create something that she felt was timeless, classic, and clean. I remember all of our fittings and making sure that the lines of the dress were clean and sharp, and the back was all very specific to Karen. I love that dress. I think that color just was one of those statement colors and was great on camera. 

Petrie: I was the one who said, “When you appear in that dress, you have to do a full turn on the stairs.” And obviously, it wasn’t hard for Matthew to [be in awe of] that stunning dress. I certainly know that we could have sold a lot of them.

McConaughey: [Kate] in that dress was 100 out of 100 knockout. It completely worked. I will tell you something funny about the poster. We found that pose where we were kind of leaning backward looking over each other’s shoulders. She’s in that long, elegant, yellow dress, and I’m in a classic black tux, back to back. It was the perfect posture to represent the film. Now if you’ll notice, quite a few—and I’m in a couple of them—rom-coms repeated a version of that same dance for their posters. 

Obst: It’s in the Costume Designer Hall of Fame. It’s a style that’s being used still right now, which is that kind of a camisole top, so it’s oddly not out of date for a movie from then, fashion-wise. Taking care of that diamond was a real pain for production because we needed security people and an armored car and all of this stuff all the time. 

Petrie: The security guards that you see on camera are real security guards [from] Harry Winston. We had to hire these guys. If I said, “Okay, cut,” all the cast had to line up and turn in the jewels. They couldn’t go to the bathroom with the jewels on. If you had to leave the set for any reason, you had to turn in your jewelry.

Hudson had to play down the fact that she could sing when she and McConaughey delivered a stage performance of “You’re So Vain” with Marvin Hamlisch. 

Hudson: We knew we were going to use that song before we started. 

Obst: [Marvin] was scripted. We asked him to do it and he said, “Yes.” Those were our two hardest days of shooting. He was a pro and fantastic, but getting “You’re So Vain” to be bad, but not so bad that you don’t want to watch the scene, is a really hard thing. 

Hudson: I had the most lovely call with Carly Simon before we made the movie. I was like, “We’re so excited,” and she’s like, “Well, sing it.” I was like, “No!” I was so embarrassed. She kind of was like, “Come on, give me a little taste of what you’re gonna do.” I was so embarrassed because I’m such a huge Carly Simon fan. But I’ll never forget it. She was so great [and] gave us her blessing.

Petrie: Matthew is not a natural-born singer, so it was perfect for him because he’s having to talk-sing anyway. Kate had the tougher job because she’s a wonderful singer, but she had to sing badly. 

Hudson: For me, it wasn’t about like, “Oh, don’t sing good” or “Try to sing bad,” it was more about what are we doing? I’m embarrassed, I can’t stand this guy, and I just want out. But then there’s a little bit of competitiveness that goes head-to-head with him. I think of all of those things, that made it fun to watch.

Petrie: I know that I shot a lot on it, and there were times where—the actors probably still don’t know this to this day—that it started to get too angry in the singing. 

Hudson: It was challenging because you’re finding the balance of “over the top,” “We’re going to do the big rom-com set piece,” and trying to fight feeling like it [wasn’t] organic. There’s a balance in it. 

Petrie: You have a cast like that together, and all of a sudden you have Robert Klein, who had done Broadway musicals with Marvin Hamlisch, and he gets up and improvises a song about How to Lose a Guy in 10 Days with Marvin improvising on the piano. They do a whole number. Then Bebe Neuwirth gets up and does the opening number from A Chorus Line, and we’re supposed to be shooting. We filmed the whole thing, even though it was probably putting me over time, over schedule, and costing me a fortune. But it was great fun.

There was never a world in which Andie and Ben didn’t end up together, but there was some back-and-forth on exactly how that would happen in the film’s ending.

Obst: We had some problems writing that ending. I think it needed to be rewritten during production. It was very easy to overwrite, and so we wanted to underwrite. We had to shut down the bridge to block it. 

Petrie: Because it was post–9/11, there was absolutely no way in hell they were going to allow us to shoot on any bridge. And yet that was what was in the script. Our location manager Sam Hutchins found that the Manhattan Bridge was under construction, so you saw how work was going on there. Well, there was actually work going on, and he found out that it was the construction company that had the permit to either shut the bridge down or not. So we went to the construction company, and we were able to go in and shoot on that bridge that scene. Mind you, Matthew really rides a motorcycle, a lot of that was really him. A lot of it was him being towed because I’m not going to have a crash with my lead actor. I’m not going to put Matthew in the hospital. 

Obst: I don’t think there was a moment where it happened at the airport or anything like that—and there certainly wasn’t a moment where they didn’t get together.

Petrie: That scene might have never been the same without that iconic ending. And again, I love the fact that when he goes to the office, [Ben] finds the dead fern on her empty desk and brings it to [the bridge]. It was just one of those things that managed to come together.

To this day, How to Lose a Guy in 10 Days remains a rom-com favorite because of the characters and chemistry.

Hudson: It’s actually quite [a] feminist movie, and I think that really resonates with young girls: The concept that women are in control of their own destiny, their own life, and their own purpose and the fact that Andy is a journalist [who’s] working a job that isn’t really what she wants to be doing, and she chooses to pursue her dream. It’s a very strong female character that a lot of women connect to. 

 Hahn: I think this movie just is joy: beautiful humans and souls, a complicated-enough setup, real female friendships, a woman with ambition and the ache for authenticity. Kate and I just did a junket and can’t tell you how many journalists said they were inspired by Andie Anderson. You can just feel it has good vibes. Also, the yellow dress. I mean, come on.

Obst: Each genre has a different necessary set of ingredients to take off, and in romantic comedies, that set of ingredients [is] chemistry and writing. It doesn’t have to look like a Chris Nolan movie. I think there were two reasons [why it worked]. One is [that] they were perfect chemistry in that movie, and that’s what makes a romantic movie. They were magic together. I think the other reason is that sometimes rom-coms seem easy, and so people do terrible versions of them because they’re supposed to be easy. Some of the best writers I’ve ever worked with worked on this script, and at the same time, it took flight, it became something bigger than it was because of the casting. 

Hahn: Kate and Matthew just had this golden aura around them—just generosity, fire, and fizz—and clearly all these years later, [it’s] so rare. [Matthew] was a total pleasure. What a peach of a person.

McConaughey: It’s really fun as the audience member to be in on the joke with one character while the other one is not. How to Lose a Guy in 10 Days has so much fun audience engagement and participation in this way.

Petrie: To me, it’s relatability [that solidifies its legacy]. When we were testing the film, you expect a rom-com like this to have a higher rating from women than men. With women, we were at 99%, and with men, which we thought would be a considerable drop-off, it was about 89%. So that meant we had a percentage of 94%.

Hudson: [My daughter] Rani discovered Sephora, which is a conversation in itself [and] we went in there. These 14-year-old girls were running up to me at Sephora being like, “Oh, my God, I love How to Lose a Guy.” Like, oh, my God, 20 years later. I was like, “Wow, this movie just keeps living.” It’s pretty amazing to have been able to do that and still affect another generation.

While there are no plans for a sequel, Hudson has some thoughts on where Andie and Ben are now.

Buckley: I hear rumblings about [a sequel] from time to time. But then I never see it go anywhere, if that makes sense. The story came about at a time when it was all about the high-concept idea. And this was a very high-concept idea.

Petrie: I don’t know how you would do it, frankly. I don’t think it would be the same without Kate and Matthew in it. I know that the ladies who wrote the original book have written these stick-figure how-to books. But it’s beyond me. It would have to be a writer coming in with an amazing pitch of how they're going to sequel-ize this.

Hudson: People always ask us [about a sequel] but there’s nothing in the works. I love working with Matthew, so I’m sure at some point we’ll work together again. My hope is that [Andie and Ben] are happy, they’ve got a bunch of kids, they got married, and they’re still playing Bullshit with his parents. If there was a sequel, I’m sure there would be some conflict in there somewhere.