As early 2000s fashion comes back in style, the era’s classic romantic comedies like “How to Lose a Guy in 10 Days” should come back with it. Rom-com veterans Kate Hudson and Matthew McConaughey star in this adaptation of Michele Alexander and Jeannie Long’s 1998 picture book titled “How to Lose a Guy in 10 Days: The Universal Don’ts of Dating.”
Set in the early ‘90s in New York City, the film opens on Hudson as Andie Anderson, a columnist known for her how-to articles in the fictional women’s magazine “Composure.” While comforting a coworker after a week-long relationship, she is inspired to write a new article: the titular “How to Lose a Guy in 10 Days,” where she attempts to convince a guy to break up with her in 10 days or less using common relationship mistakes women make.
At the same time, advertising executive Benjamin Barry, portrayed by McConaughey, is competing to head an advertising campaign for a diamond company against two co-workers. In an attempt to prove his ability to market to women, Barry places a bet with his boss that he can make a woman fall in love with him before the company party in 10 days.
When Anderson ends up at the same bar where Barry’s work meeting is taking place, his co-workers choose her for the bet, having heard about her newest article earlier in the day. Following a successful first date, the couple enter a tug-of-war where Anderson and her co-workers tear the relationship apart while Barry and his co-workers try to keep the relationship together.
Anderson’s tactics, like making Barry miss the tie-breaker of a Knicks championship game, getting a dog after five days together and creating a photo album of their fake children using Photoshop, worked too well and caused him to break it off after only six days. Following a suggestion from his friends, Barry suggests couples therapy to buy time until the company party. Anderson’s co-worker, Michelle, poses as a couple’s therapist and humiliates Barry before encouraging the couple to meet his family together, where the couple ends up getting along and forming a genuine connection right before the 10 days are up.
At Barry’s company party, things come to a head as he and Anderson accidentally find out about each other’s plots. Anderson embarrasses Barry by inviting him to sing on stage, but he retaliates by making her sing a duet with him, leading to a painful rendition of Carly Simon’s “You’re So Vain” and an argument that causes the two to go their separate ways.
Barry wins the ad campaign, and Anderson finishes her article, but neither party is happy without the other. He ends up reading her article, where she announces, “I lost the only guy I’ve ever fallen for,” and is leaving for Washington DC. He chases down Anderson’s taxi on her way to the airport, leading to the couple reconciling on the side of the Manhattan Bridge.
“How to Lose a Guy in 10 Days” seemingly fell from the “classic rom-com trope” tree and hit every branch on the way down, making the plot a little predictable. Despite this, Hudson and McConaughey’s performances, along with the dynamics between their characters’ respective friend groups, make the classic movie a fun, worthwhile watch.
The film is available to stream on Peacock and Pluto TV.
