the expert level mind games of How to Lose a Guy in Ten Days

welcome to the second entry in Rom Coms Revisited <3

This time, a reader request! I have to admit, I was less familiar this one. Before my rewatch I’d seen it maybe twice before. So I’m going in with less nostalgia but a lot of curiosity.

The Wikipedia synopsis: How to Lose a Guy in 10 Days is a 2003 romantic comedy film directed by Donald Petrie, starring Kate Hudson and Matthew McConaughey. It is based on the picture book of the same name by Michele Alexander and Jeannie Long. The book has no narrative, only a list of comedic dating "don'ts", so the characters and plot were created specifically for the film. In the film, advertising executive Benjamin Barry makes a bet that he can make any woman fall in love with him, while women's magazine writer Andie Anderson plans to write an article about how she led her boyfriend to dump her, putting them at cross-purposes after they choose each other as their romantic partners.

First, some background: Kate Hudson’s Andie writes a “how-to” column for Composure mag. She works with her friend Michelle, played by the unrivaled Kathryn Hahn (whose talent is sadly squandered by the casual misogyny of early 2000s writing). As they’re walking into work one day, Michelle is struggling to get over the breakup of a week-long relationship. Andie reminds her, “You only dated the guy a week.” Michelle tearfully responds, “It was the best week of my life.”

Later, in a staff meeting, the central premise is born. Andie suggests, “Look at Michelle [Kathryn Hahn]. She’s a great girl, right? An amazing woman. But, she has a problem hanging on to relationships. And doesn’t really know what she’s doing wrong, which is like a lot of our readers. So, I was thinking that I could start by dating a guy and then drive him away. But only using the classic mistakes most women, like Michelle, make all the time. I’ll keep a diary of it and it will be sort of a dating how-to in reverse.”

Of course, this framing puts the blame for failed relationships squarely on women. Andie’s boss immediately dubs the article, “How to Lose a Guy in 10 Days”. Andie asks, “Why ten days?”. Her boss explains, “Five days is too short and we go to press in 11.”

That night, she meets Matthew McConaughey’s Ben Barry at a bar. At this point you might be thinking, how hard could it be to get someone to break up with you? But there’s a twist: in order to land a new advertising account, Ben made a bet with his employer: he has ten days to make Andie fall in love with him.

So now we have directly competing goals:

• Ben wants to make Andie fall in love with him

• Andie wants to make Ben break up with her

They go back to his house, where Ben puts Nelly’s Hot In Herre on the CD player.

But then he remembers he’s trying to make her fall in love, so switches to everyone’s fave groovy romancer: Al Green.

Andie strategically leaves her purse at his house. The next day, at work with his friends, Ben muses, “A woman’s purse is her secret source of power.” Ben, babe, men can carry purses too. But anyway, he goes through the purse and finds the Knicks tickets Andie left for him to find.

For the sake of time, at this point we’re going to switch to bullet points.

A list of things Ben does to try to make Andie fall in love with him:

• Sends her 100 white roses

• Cooks her dinner one time (lamb w/ a cherry glaze & carrots)

• Suggests couples therapy

• Takes her to Staten Island to meet his fam

• Teaches her to drive a motorcycle while this (incredible) song plays in the background

A list of things Andie does to try to make Ben break up with her:

• Sends him to the concessions stand to get her a Diet Coke during the final moments of a Knicks game

• Calls in the middle of a meeting to tell him she misses him

• Takes him to see Sleepless in Seattle in theaters, where she gets him punched in the face by a random dude

• Redecorates his home, including a fuzzy pink toilet cover, stuffed animals, a framed photo of her, and a baby fern plant

• Plays him Carly Simon’s You’re So Vain, changing the lyrics to “And all the girls dreamed that they’d be Ben’s partner, they’d be Ben’s partner”

• Pretends to be vegetarian

• Names his dick Princess Sophia (sight unseen)

• Doesn’t have sex with him

• Gets a tiny dog and dresses the dog & Ben in matching Burberry

• Creates a photoshop-generated photo album for their non-existent family

• Calls his mom, Glenda

• Puts Vagisil and other “gross” products in his medicine cabinet (he really doesn’t like this one)

• Shows up to “boys night”, letting herself in with a key she had made

But honestly, how many of these things are that egregious (I mean obviously other than the punching one, and maybe the photo album). For many of her tactics, my opinion is something along the lines of “But like who cares if she leaves Vagisil in his apartment?”. My takeaway here is an obnoxious central theme of these rom coms: making women feel/seem crazy for having needs/preferences/desires. Eventually Ben actually says it explicitly, “You’re acting completely insane. You’re like a freakin’ one-woman circus, Andie.”