Culture / Entertainment

From Cocktail Napkin Drafts to Casting What Ifs — The Best Friends and Authors of ‘How To Lose A Guy In 10 Days’ Reflect on Its 20-Year Legacy

And How Their "Tactics" Would Stand Up Today

BY // 02.14.23

When I’m questioned about fond and fun memories of living in LA, I often find myself sharing a somewhat inspirational story. That two of my dearest friends, Michele Alexander and Jeannie Long, whom I had known since high school, decided to write a book that became the source material for one of the most beloved rom-coms of all time starring Kate Hudson and Matthew McConaughey.

A few years after graduating from Florida State University, the two best friends found themselves living in Los Angeles, where Hollywood loomed in the background. Jeannie and Michele decided to write a book and leaned into what they knew. What emerged was How To Lose A Guy In 10 Days: The Universal Don’ts of Dating.

You’ve likely seen the flurry of online stories out there recently celebrating the film’s 20th anniversary. One clickbait headline that immediately caught my eye: Kate Hudson Convinced Producers to Cast Matthew McConaughey in How to Lose a Guy in 10 Days. And Vogue’s 30 Thoughts I had while rewatching How to Lose

In celebration of Valentine’s Day, I asked Jeannie and Michele to answer a few questions about those heady days surrounding the opening and some thoughts on what they think of their book now — 20 years later.

The book behind the blockbuster rom-com.
The book behind the blockbuster rom-com.

PaperCity: What was the genesis of the story?

Jeannie and Michele: One night, when we were first in Los Angeles in our early 20s, after a long night out and many drinks, we were talking about dating and the book The Rules. The Rules, at that time, was kind of a staple in every single girl’s nightstand and to put it kindly, it was rather frustrating. It was all about playing games, acting a certain way, and changing yourself and your behavior to become an acceptable partner for a man. It seemed so archaic and was nothing like the way we acted when we actually liked someone. We knew we couldn’t be the only ones that felt this way. So, we thought it would be funny to write a book about what girls really do in relationships when they like someone.

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We were hungover, watching football and laughing as we wrote down every crazy thing we could think of that we had ever done in any of our previous relationships. At this point,  Jeannie and I had already been best friends for over 10 years, so there was no hiding anything from each other about our less-than-perfect dating histories. That night, we went to a concert at the Whisky-a-Go-Go and spent most of it at the bar writing the bulk of the book on cocktail napkins.

The next day, Michele said she thought we really had something. We started to put them in order and pulled out some crayons to illustrate them. Once we had it all together, we printed up some copies and glued them together to assemble the book. The plan was to give them out as Christmas presents. Michele’s Brother, Brian was a talent agent at the time at Writers & Artists and we finally harassed him long enough that he took it into the office one day to show some literary agents. The next thing we knew, we had an agent and a book deal with Bantam Books. Then, Robert Evans and Christine Peters, from The Robert Evans Company at Paramount, got a hold of the Kinko’s bound book we made and were calling us to option it and make it into a movie.

The book was released a year later in 1998 and the movie was released five years later in 2003. Gwyneth Paltrow was first attached but fell out. Then Producer Linda Obst brought in Kate Hudson and Matthew McConaughey and the dream cast was born. At the end of January 2003, the studio sent us on a press tour the week before the movie premiered. The first time we met the director, Donald Petrie, at a screening on the Paramount Lot he told us he changed the names of Andie’s two best friends to Jeannie and Michele as an homage to us.  The whole thing was so surreal and all this just from ideas on bar napkins to stick figures on a Kinko’s bound book meant for Christmas presents for our friends.

How To Lose A Guy In 10 Days authors
Authors Michele Alexander and Jeannie Long in LA in the early 2000s (Images provided by Michelle Alexander and Jeannie Long)

PC: Do you think you’d change any of the 10 Days “tactics” based on the world we live in today?

Jeannie and Michele: Technology and social media have changed everything. Back in the day, if you wanted to do a little light stalking, you might drive by his house to find out what was going on. Now, you can go online and go down a rabbit hole and find out pretty much anything you want, in real time.  You could piece together histories, timelines, inconsistencies… it’s a whole new stalking ballgame out there now.

Authors Michele Alexander and Jeannie Long facing fashion emergency for the book (Images provided by Michelle Alexander and Jeannie Long)
Authors Michele Alexander and Jeannie Long facing a fashion emergency for the book (Images provided by Michelle Alexander and Jeannie Long)

PC: What have you written since How to Lose a Guy in 10 Days?

Jeannie and Michele: A few other books. We were busy writing some follow-up How-To books in the years that followed — How to Tell He’s Not the One in 10 Days, How to Get a Guy in 10 Days, and How to Get Over a Guy in 10 Days. We then wrote 365 Reasons Why I’m Still Single to which we are well over 5 more million reasons why we are still single. We like to write about what we know. In our next book, we’ll be tackling menopause. Why don’t people talk about this more?

How To Lose A Guy In 10 Days authors
Authors Jeannie Long and Michele Alexander in LA in the late ’90s (Images provided by Michelle Alexander and Jeannie Long)

PC: Where are you guys now?

Jeannie and Michele: Still single. Still living in Los Angeles. And still best friends  forever.

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