33 thoughts while watching ‘How to Lose a Guy in 10 Days’ from an off-duty therapist
The first half was more painful than I remembered but the chemistry between these two is off the charts. Also, did this movie alter the course of my life? Let’s see, shall we…
This is a segment, dialoguing on dialogue, where I briskly explore a piece of media–TV, movies or music—with first thoughts. Inspired by Emma Specter’s column for Vogue where she narrates her thoughts as she watches a movie, movie trailer, or gets a first look of an upcoming movie. This is my take on that, weaving my personal reflections together with any therapeutic concepts I stumble upon along the way.1
One thing before we jump in, I show up very much as myself here. Myself first, and all my other labels are secondary. If a therapist speaking candidly feels like too much to your system, that is absolutely is OK and this may not be the best particular newsletter for you.
As you may be able to tell,2 I love a rom-com. A film snob you will not find here.
One of the most seminal from the genre for me is How to Lose a Guy in 10 Days.
HTLAGITD stars Kate Hudson and Matthew McConaughey at the height of their powers. Kate plays Andie Anderson, a magazine columnist in NYC who agrees, in a moment of panic to “save” a friend from humiliation, to write a piece about all the things women can do to drive a guy away, specifically in 10 days (“because a week is too short and we go to press in 11”). Meanwhile, across Manhattan, Matty boy, playing Benjamin Barry3, is an ad exec who, to get a new account, boasts that he can get any woman to fall in love with him in 10 days. As fate would have it, these two scheming rapscallions cross paths and we are off to the races on the plot of the 36th ranked Best Romantic Comedy of All Time (so says this Vanity Fair list, anyway).4
According to Director Donald Petrie the film did incredibly well in test screenings, “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%.” Petrie alleges the industry average at these screenings is 54%.5
All in all, this means that HTLAGITD is the perfect val/pal/galentines film. Currently, you can find it to stream on Peacock or Paramount+, for purchase or rent on the Jeff Bezos machine AND I noticed two theaters by me are playing it, probably because of Valentine’s Day so check your area, too, if you want the full experience.

CAST
Andie Anderson played by Kate Hudson
Benjamin Barry played by Matthew McConaughey
Michelle played Kathryn Hahn
Jeannie played Annie Parisse
Tony played by Adam Goldberg
Thayer played by Thomas Lennon
Spears played by Michael Michele
Green played by Shalom Harlow
Lana played by Bebe Neuwirth
This film found me at a critical time in my development. At 14 years old, I had yet to kiss a boy or really even date one, but the crushes were aplenty. All the romance I’d experienced existed within the confines of my own mind.
HTLAGITD injected a bit of glamour, passion (the fighting kind) and Matthew McConaughey’s abs and southern drawl into my fantasies…and also my desire to be as effervescent as Kate Hudson.
Once it came out on VHS–lord, help me–I watched it over and over. There was a year in high school where I fell asleep to it nearly every night.
What proceeded was a deep love for both Matt McC and Kate Hudson, but other than that I don’t know what I took from this film. I’m curious to see if I will watch it with the same teenage lens of my first viewing or if the decade and a half that have passed since I last watched it will have altered my perspective.
Ahhhhh. The credits music is early 2000’s sugary sweet and these columns flashing are not exactly what we’d call feminist leaning. Which I know is the point—she wants to write about politics—but this was not something I clocked when I watched it as a teen. For instance, “How to Get a Better Bod in 5 days” was one of her columns. As a former Cosmo consumer, this all tracked. No questions asked. 🤦🏼♀️
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