Date Night Movies – Part #3


Date Night Movie Series

Welcome listeners! This marks our last episode of the “Date Night Movies” series. Each week we have been suggesting two movies that you and your loved one can watch.  We discuss some important themes in the movies, along with questions you can ask each other after you enjoy the movies. 

Today we are talking about “How To Lose A Guy In Ten Days” and “27 Dresses.” We’re taking a detour from the more serious movies from the last two weeks and taking a look at two lighthearted, albeit contrived rom-coms. Have fun!


How To Lose A Guy In 10 Days

How To Lose A Guy In Ten Days

Andie is an ambitious journalist that wants to write about religion, politics and ethics. She writes, however, for Composure, a Cosmopolitan-like women’s magazine.  When it is time to pitch ideas for the newest issue, Andie’s editor-in-chief Lana makes it clear that she will be expected to contribute yet again another superficial article.  Andie’s friend and co-worker Michelle struggled to make it to the meeting that morning—she was suffering from the blows of ANOTHER breakup. This inspires Andie to pitch the article idea of “How To Lose A Guy In Ten Days.”  Lana loves the idea and encourages Andie to find a man and put him through all the ways women drive their boyfriends away.

Ben is in advertising and is vying for the DeLaurer account, but he has competition. His co-workers, Judy and Judy (yes, you read that right), have just visited Composure the day the pitches were made for the newest issue. As Ben’s boss describes the newest project, Ben bets him he can make any woman fall in love with him.  His boss says that if he does, he will give him the project.  The Judys suggest to their boss that the woman that Ben must attract has to be Andie while at a party. (This is done without the boss or Ben being aware that Andie is working on a project of her own on how to drive men away.)

Does Ben fall in love with Andie, who does everything in her power to make him break up with her? Watch the movie and find out!

27 Dresses

27 Dresses

Jane loves her boss George, she just doesn’t know it yet.  He is self-made, moral, and a hard worker—all traits that she possesses herself.  Enter Tess, Jane’s younger sister.  Unbeknownst to Jane and George, Tess has a few secrets.  She has been dumped by her boyfriend and lost her job.  She is spiraling, but she lets no one know.  Instead, she falls for George and he falls for her.

Jane has a quirk.  She’s always the bridesmaid, in fact, she has twenty some odd bridesmaid dresses hanging in her closet to prove it.  One night while performing in several weddings AT THE SAME TIME, she meets Kevin during a cab ride. Kevin does not let on that he is the commitments columnist for the newspaper. When Jane leaves her planner in their cab, Kevin discovers Jane has an interesting past-time. He is fascinated by Jane’s devotion to being the perfect bridesmaid.

George and Tess are moving TOO fast.  The pair decide to get married only weeks into their relationship.  Kevin is contacted to cover their wedding festivities. When Kevin puts it together that Tess and Jane are sisters, he concocts a plan to write an article on Jane’s peculiar constant bridesmaid status. 

Kevin and Jane spend quite a bit of time together in getting ready for Tess’ wedding.  He confronts her about her obvious love for her boss.  Meanwhile, Kevin and Jane have their own chemistry simmering below the surface. A character-revealing slideshow at Tess’ wedding rehearsal threatens the impending wedding ceremony.

Does George find out that Tess has been lying to him about who she really is?  Does Jane and George end up together?

Major Themes in How To Lose A Guy In 10 Days & 27 Dresses

Perfectionism & People-Pleasing

It could be said that Lana and Andie have laser focuses on what they want in life and that’s where the conflict starts in “How To Lose A Guy In Ten Days.”  Lana’s magazine, Composure wouldn’t be what it is without sticking to a very specific tagline. Andie hasn’t come all this way to just write for trashy chick rags.  Somewhere along the way, however, Andie hasn’t had much of a life. Her focus on her career has put having a love life way beyond the back burner. Perfectionism may be what has kept her from having a life outside of writing. People-pleasing has kept her in good graces with Lana and employed for a magazine that she really doesn’t believe in.

For Jane in “27 Dresses,” she has performed “perfectly” for her boss. She bends over backwards to her own detriment to keep him happy. He even tells her that she performs beyond his expectations.  It strokes her ego.  This behavior acts as a mild substitute for love with Jane.  She acts also as a people-pleaser to her sister, enabling her childish behavior, rather than calling her out on it.  Jane ends up being a great example of what happens when a people-pleaser has said ‘yes’ to much—she acts out in a very passive-aggressive way that shocks everyone. 


In “How To Lose A Guy In Ten Days,” Andie basically does just about every classic codependent behavior in the book to send Ben running.  Ironically, it doesn’t work.  His desire to win his bet forces him to behave very empathically. He learns how to cope with an unstable significant other.  He listens.

Jane fulfills the role of “family hero” in “27 Dresses”.  The loss of their mother was difficult for Jane and Tess.  Jane becomes a mother-like figure to Tess.  This gets the both of them in trouble. Tess ends up relying too heavily on Jane to be responsible for her.  Jane feels a sense of satisfaction for playing this role.  It’s not healthy, but often in relationships such as these it is seen as benign and even good.


It takes confrontation in both movies for the different couples to face how they really feel about each other. In “How To Lose A Guy In Ten Days,” Andie learns from Ben that if you want real love, you can’t play games.

In “27 Dresses”, Jane’s friend Casey, explains to her that if she had been direct and upfront in the beginning, so much hurt and chaos could have been avoided. Jane had to come to terms with the fact that she had been allowing her perfectionism to stroke her ego as well as fuel the platonic relationship with her boss. Kevin also confronts Jane and helps her to determine where her feelings are really coming from.

Post-Viewing Questions

After you and your significant other watch the movie together, ask each other these questions.

Which relationship do you identify with most?  How?

What’s been the theme/s in your relationships?

What do you think will happen to the couples after the movie?

What did each individual need to do to make the relationship work?

Published by

Vincent & Laura Ketchie

Vincent Ketchie, LPC and Laura Ketchie, LPC are the hosts of Relationship Helpers, a podcast where they discuss family issues and interview relationship experts. Vincent and Laura are licensed marriage counselors.

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