I Tried to Lose a Guy in 10 Days. Here’s What Happened.

Photo: Paramount Pictures

When I agreed to sabotage my shallow desert grave of a personal life by re-creating the morally reprehensible antics of characters played by Matthew McConaughey and Kate Hudson in the vaunted Robert Evans picture How to Lose a Guy in 10 Days, I had not seen the film since 2004, when I was extremely drunk on an airplane. It’s basically this: A writer named Andie Anderson thinks she is too good for women’s service journalism. Instead, she wants to write a column about civil unrest in the Central Asian republic of Tajikistan for the Cosmopolitan-esque magazine where she works, which is ridiculous. To please her editor, she accepts a creepy, nonsensical assignment: to lose a potential romantic partner in less than a fortnight by doing all of the awful things women typically do to make men flee from us. Did you hear that? That’s the foghorn I blow when I want to signify that something very meta is afoot.

The titular “guy” in this filet cut of cinema is advertising exec Ben Barry (Matthew McConaughey in peak pre-prestige, ambulatory foam-finger mode). Andie’s job is to attract, enchant, and then sicken Ben with her presence so much that he goes away forever and ever. Don’t worry — there’s a deeply stupid double-bind: Ben has extra-coincidentally made a grotesque wager with his co-workers that he can make a woman fall in love with him before some upcoming office party. The party is a week from Sunday — in TEN DAYS! If Ben succeeds, he gets to pitch a slogan to the world’s biggest jewelry conglomerate. Ben wants this ad account so badly he’s willing to remorselessly pulverize the spirit of a flesh-and-blood, feeling person. I guess that’s just how much he loves blood diamonds. For 116 honeyed minutes, Ben and Andie act insane in rigidly codified, gender-normative ways. Alas, neither is able to leave the other because: money. Eventually they fall in love, to the delight of a raw, pretty recently post-9/11 America.

Could I successfully make a living diorama of this horror show? Well, the acting-insane part I knew I could handle. It was the “ten days” that were problematic for me and — let’s be real — the structural integrity of this movie. Quickly repulsing somebody would be a snap, but it’d also make for a short flick and a shorter article. I would have to try to do as she did and ramp things up from “slightly annoying” to full-on eating-from-the-garbage, writing-on-the-walls-in-my-own fluids psychosis — over exactly ten days.

Fortuitously, I’d just started gingerly hanging out with a guy who was visiting L.A. for work. This made him a good candidate because our relationship already had an expiration date, and I had also begun to like him in a pathetically un-chill, human-person way. It was time to end this on my terms: by making him hate me. You may be thinking that this is not a nice thing to do. But if I learned anything from How to Lose a Guy in 10 Days, it’s that love is a heinous abstract construct. Also, sleeping with a writer is basically like putting a scorpion in your pants.

Note: Trying to replicate all of the actual behavior from the movie wasn’t always physically or financially possible or — let’s be honest — something I could do without being hospitalized. Below is what happened between me and Miller Lyte, which is what I will call the poor, wonderful human being I did this to. Because it is Matthew McConaughey’s nephew’s actual name, and I don’t ever want anybody to forget that.

DAY ONE: Calling Too Much
According to the film, one of the things men hate most is being called a ton. Unfortunately, I live in a canyon and there is very bad cell-phone reception. So I just text him a lot. It turns out he’s totally fine with this, and he’s also a recreational stimulant user. He texts back whenever I text him, pretty much right away. Oh man. Clearly this is not the first time a woman has tried to lose this guy in ten days.

DAY TWO: Ruin Sports
On their second date, Andie takes Ben to see the Knicks, but then she won’t let him watch the game, whines for diet soda, and calls him by an obnoxious nickname. Wow, women are the worst.

Miller Lyte REALLY likes football, so when we watch some together I figure I have this one in the bag. I frequently ask, “Why are you yelling?” and make helpful suggestions like, “Well, if it upsets you this much to lose money, then maybe you shouldn’t be illegally gambling.” Finally, I wrap my arms around him and ask, “Am I talking too much, Old Meat?” because I think it would bother most men to be called that. He predictably does not like to be called Old Meat but later actually warms to it.

DAY THREE: Girl Things
The first time Andie goes to Ben’s house (again, to watch the sports game and eat meat because, MEN, RARRRGHHH) she brings stuffed animals, tampons, and a fern. You’ll be shocked to know that I own exactly zero stuffed animals, and this dude is not getting the fern I work so hard to almost not kill, so tampons it is. Upsettingly, the owner of his Airbnb has left a full complement of toiletries for guests. That’s right: There are ALREADY TAMPONS AT HIS PLACE. What are the odds?! Fuck the share economy.

DAY FOUR: Chick-Flick Marathon
Ben tells Andie she can pick the movie. Smash cut to: a theater where the marquee says “CHICK FLICK MARATHON.” Yep, that happens. In a commercially successful film.

So I go to his house and I tell him I also want to watch Brokeback Mountain and You’ve Got Mail, back to back, which I figure constitutes a chick-flick marathon and ups the ante because straight men don’t want to watch movies about gay guys doing sex, ever. During both films, he mouths along with a lot of the dialogue.

DAY FIVE: Food Issues
Even though she houses a lobster at their first meeting and loooooooves bacon (buckle up if you love that joke, people of 2004!), Andie pretends to be a vegetarian to annoy Ben. There is nothing more manly than hating vegetarians, because it represents sublimated jealousy for the female ability to demonstrate compassion without social reproof.

Sadly, I can’t do this because I have already eaten a ton of meat (heh) in front of Miller Lyte, so as a compromise I don’t finish half of an elaborate Italian sandwich he makes me. This is basically the craziest thing I’ve ever done in the name of journalism. For the first time, I see some hurt in his eyes.

DAY SIX: Nagging About Cigars
If I know anything about all men, and I know lots, it’s that they hate to be nagged. Particularly about their cigars. Andie nags Ben and his friend a bunch about their cigars.

Miller Lyte doesn’t smoke cigars, but he does dip, which is equally gross. Actually, no — it is definitely even grosser.

At his place I pick up his dip and say, “You’re a piece of human garbage.” Nag, achieved!
“You would actually look pretty cool with a big wad of tobacco in your mouth,” he says, tucking some into my lower lip.
“Rear-ry?” I say, posing in front of the mirror. He’s not wrong.

DAY SEVEN: Being Terrible at Sex
This is when this film begins to get truly Faces of Death–level messed up: In the film, Andie calls Ben’s dick “Princess Sophia,” causing him to lose his erection.

Sophia is my sainted aunt’s name, so I won’t be doing that, and it turns out this guy has already named his penis, because of course he has. Even though it kind of goes against the spirit of this exercise, I am definitely not going to make him lose an erection. I’m writing a damn article, not trying to ruin my sterling international sex rep.

DAY EIGHT: Stevie Nicks
Andie brings a bunch of CDs to Ben’s. Sounds great, right? WRONG. The singers are all women! DAY EIGHT, PLAYA. She plays him “You’re So Vain,” which is a great song, but Ben looks like she just laid eggs in his body.

This is a fairly easy one to replicate, and besides: It’s time to get the nuke codes for this thing. I put on Stevie Nicks at Miller’s and sing along to each track. It should be noted here that I have a voice like a crystal dinner bell, so I have to actively try to sound bad.

This backfires like an antique musket. He likes Stevie Nicks! He sings the man parts in “Leather and Lace”! AHHH. HOW IS HE DOING THIS? HE IS NOT GOING TO GET THAT DIAMOND ACCOUNT. NOT IF I HAVE ANYTHING TO SAY ABOUT IT.

DAY NINE: Make Composites of What Our Kids Would Look Like, Get Him a Dog, Take Him to a Fake Therapist, Get Him Punched in the Actual Face
Oh, Jesus Christ. I almost feel bad for Ben because all of the above things actually happen to him. But let’s not forget that making somebody love you so you can come up with the new “He went to Jared!” is awful, too, so I don’t know, maybe they deserve each o— NO MOVIE. I WON’T LET YOU MAKE LOGICAL SENSE.

Instead of all that stuff, I just try to do something equally crazy, because it’s Day Nine after all and Andie and I have a deadline. So, I get wildly drunk on Fireball and shave matchbook-size chunks out of his hair with an electric pubic-hair trimmer. He finds this charming. What happened in the decade since this movie? Is this Zach Braff’s fault? I don’t know whether to send Zach Braff flowers or hurtling into deep space.

DAY TEN: We Physically Separate by Several Thousand Miles
He goes back to New York as planned. Unlike in the movie, we do not have a charming karaoke battle/car chase that ends in two lunatics deep-tonguing each other. Nobody gets the diamond account, and I don’t think I will get a column about Tajikistan in Cosmo out of this. Also, I think I may now be addicted to dip. I don’t know whether we’ll see each other again; for now, the experiment and we are decidedly over. I have lost the guy, and it gives me no joy. But Miller? If you’re back in New York and reading this, just know: It doesn’t look that bad and will grow back really soon if you take prenatal vitamins.

How I Tried to Lose a Guy in 10 Days