Best romantic comedies...and the lessons we can learn from them about work

The romantic comedy is one of the most well-known and profitable film genres. These films typically include musings about love, heartbreak, partnership, and self-development– and, of course, humor and hijinks. 

If you’re like me, then you believe that springtime is prime time for watching (and rewatching) rom coms. The birds are singing, the cherry blossoms are blooming, and people all over cities and suburbs are setting out their picnic blankets in the park. There’s magic in the air, as is the case in many of the most beloved romantic comedies of all time. 

But even in Springtime, and even in rom coms, people still have to work, because work makes up one third of our lives. This is evident in the plot of so many romantic comedies– a large proportion of these films are actually set at workplaces. Whether that workplace is at a bookstore, an office, a major publication, or a farm, you can look at any romantic comedy and learn something new about the role of work. 

So let’s save the love lessons for another day, and look at 5 classic rom coms and what they can teach us about work.

1. Legally Blonde

Showing up as your authentic self at work can be your greatest asset.

In Robert Luketic’s 2001 blockbuster Legally Blonde, Reese Witherspoon plays Elle Woods, a lovable and pink-clad sorority queen who makes her way to Harvard Law in order to win back her ex. Throughout the movie, she learns that she loves being a lawyer, and defies all odds to win a major case and establish herself as a successful attorney.

As the viewer, you watch Elle go from sorority queen to Harvard Law graduate, but the lesson really comes through Elle’s ability to stay authentic to herself in every environment. While her famous quote, “What, like it’s hard?” might make it seem like Elle glided into success, she does face intense adversity in her workplace. 

Despite resounding stereotypes, sexism, and harassment, Elle shows up as her bubbly and outspoken self, always in head-to-toe pink, in both the hair salon and the courtroom. Her knowledge of beauty and grooming even wins her the major case of the year, and thus launches her into a career of standing up for others. 

While Legally Blonde is funny and somewhat fantastical, it does teach us something about authenticity as an underrepresented employee in the workplace. Many underrepresented employees feel like they must conform to the norms of the workplace, even if those norms are outdated or rooted in bias. Sometimes, it isn’t safe to show up as yourself at work. But companies hire humans, not clones– and some of the greatest solutions and innovations come from workplaces that embrace diverse identities, backgrounds, and skill sets. 

So, if you find yourself inspired by Elle Woods, take a chance on yourself and embrace what makes you, well, you. You never know where your unique value proposition can open doors for you!

2. You’ve Got Mail

A lot of the time it’s not personal…it really is just business. But even in “just business,” you can still be human.

If you’re a fan of the Tom Hanks and Meg Ryan extended universe, then you have probably seen You’ve Got Mail. The movie came out in 1998, and has now been beloved for a quarter century.

You’ve Got Mail features quirky, struggling boutique bookseller Kathleen Kelly and tightly-wound, sarcastic chain bookstore owner Joe Fox. They chat anonymously over the Internet, and also happen to meet in real life… only to face extreme conflict. Joe’s bookstore conglomerate is a major threat to Kathleen’s small business, and they spend most of the movie battling it out. Meanwhile, they don’t piece together until the end that their secret internet fling is actually their greatest enemy. 

But by that time, they had already fallen in love.

Viewers feel devastated when Joe’s business finally takes over Kathleen’s, shuttering her tiny whimsical bookstore that she had inherited from her mother. When Kathleen asks for advice from her anonymous fling, he (Joe) responds over and over, “You can’t take it personal. It’s never personal. It’s just business.” 

What I love about You’ve Got Mail is not necessarily the love story, it’s the conversation around how we connect as humans when work is involved. Whether you are more of a Kathleen or a Tom, there is a lesson to learn here about balance. Joe represents corporate America, the “just business” side, and Kathleen represents the nontraditional entrepreneur, the “personal” side. When Kathleen loses her business and essentially faces a devastating layoff, she learns from Joe how to adapt, how to accept the opportunity to launch something new and follow her dreams. Joe, seemingly heartless in the business world, ends up hiring all of Kathleen’s old employees and begins to understand how important it is to see the human side of business, how important it is to connect with your base to create loyal employees and consumers.

The lesson? If you are experiencing a layoff or major disappointment, think about what a reset toward your dreams might look like. How can you take a step toward a better-suited position or pursuit? And if you are knee-deep in the dog-eat-dog mentality, take a step back and think about how you can value community and connection in your workplace. You never know how much of a difference it can make in morale (and profit). 

3. The Proposal

Leaders who lead with empathy will reap more than leaders who lead with fear.

In 2009 office rom com The Proposal, Sandra Bullock stars as Margaret Tate, a high-strung, dictatorial book editor who is feared by her employees. Ryan Reynolds is Andrew Paxton, Margaret’s assistant who is run ragged by her demands and expectations. When Margaret faces deportation back to Canada, she forces Andrew to fake-marry her so she can stay in the US. Somehow, they find themselves on a plane to Alaska, where Andrew’s family eagerly awaits their son and his new bride-to-be. This trip to Alaska eventually leads to the unlikely pair falling in love.

On landing in Alaska, Margaret is initially high-strung and stubborn as ever. But throughout the film, she begins to learn how to let loose and lean into empathy and vulnerability, which are important in relationships as they are in the workplace. Andrew’s 90-year-old grandmother (Betty White) teaches Margaret about love, being silly, and also how important it is to reconcile and appreciate family while they are here. 

By the time the trip ends, after countless conflicts and life lessons learned, Margaret is a different person– and a different leader. She addresses her own barriers to empathy and returns to the workplace as an enlightened leader who sees people around her as humans first.

Though I could watch Sandra Bullock and Ryan Reynolds fall in love all day, I am really interested in what we can take away as people managers and leaders. Margaret’s workplace in the beginning of the film is a hostile one, full of fear and disdain. Employees are burned out and scared to upset her. By the end of the film, her employees are surprised to see her smiling and receptive to connection, marking an extreme culture shift. 

Though this film offers an extreme example of sharpening leadership skills, I think we can all learn a little something from Betty White’s exuberant joy. As leaders, it is essential that we manage with empathy and maintain a person-first perspective. Leading with empathy is the best way to create collaborative, loyal teams that will stick around in the long term. 

And it doesn’t hurt to let loose and have a little fun. 

4. PS I Love You

It’s never too late to become an entrepreneur.

PS I Love You, the 2007 heartbreaker starring Hilary Swank and Gerard Butler, definitely leans more on the rom than the com. If you can watch this movie without crying, I salute you, because it’s all about rebuilding a life after losing your true love. And a little bit about how it’s never too late to discover your calling.

Gerry and Holly are each other’s once-in-a-lifetime loves, but it all comes crashing down when Gerry dies of a brain tumor in his thirties. Holly, a disgruntled real estate agent and worrywart, takes the death extremely hard. Knowing this would happen, Gerry orchestrates an elaborate scheme to help her move on from his death. He wrote her a series of letters delivered after his death to help her take chances, stop worrying, and start living again– all things she has difficulty with. 

As the film moves between present and past, you can see Holly’s development as a character. When Holly and Gerry initially meet, Holly, an art student, is lost– she doesn’t know where she is on the map, or in her life. Gerry, a reckless, happy-go-lucky Irishman, walks her back where she needs to be. Of course, they fall in love, rather easily, and the rest is history.

Years later, we can see that Holly never quite figured out her career. She breaks down at a real estate sale and quits, left with nothing but grief and an unused art degree. With Gerry’s encouragement from his final letter, Holly starts feverishly designing her own shoes. She learns how to make shoes by hand, and by the end of the film, she has finally found her life’s passion– being a successful shoemaker and designer. 

Sometimes, the road to finding the role of work in YOUR life is long and full of potholes. But if there’s anything we can learn from Holly, it’s that it is never too late to start turning your dreams into reality. Whether that’s starting your own business or embracing a career change, know that there is no timeline for your own definition of success.

5. 27 Dresses

Reflecting on and expressing your needs is the key to avoiding burnout and resentment. 

Another early-mid aughts hit, 27 Dresses stars perpetual bridesmaid and executive assistant Jane (Katherine Heigl) and her limelight-loving younger sister Tess. Jane is secretly in love with her boss, George, but Tess, unknowing, snags him first. Meanwhile, snarky wedding reporter Kevin (James Marsden) takes interest in Jane and assigns himself to write a column on her excessive bridesmaid dress collection… and her willingness to serve anyone but herself. 

Hijinks ensue, and Jane resents her sister and her boss without expressing her true feelings. She directs her anger at Kevin, who tries to teach her how to say “no.” She ends up publicly exposing her sister for not representing her true character to George, and the two split at their wedding rehearsal dinner. Standing in the aftermath, Jane has to learn how to say how she really feels… and how to say “no” when something doesn't suit her. 

Though this film ends happily, with Jane and Kevin getting married, it offers a very important lesson for women and underrepresented people in the workplace. Burnout, which is one of the major causes of resignation, can be caused by many factors (more on that here). One of these causes  is not having space to express your needs and stand up for yourself in the workplace. This inability to express oneself can lead to resentment, which can lead to a nasty case of burnout. If you struggle with expressing your needs and standing your ground, embracing community can be a good place to start. Find other women who feel the same, and begin to practice taking up space in healthy ways. 

While real life is certainly different from a rom com set, Jane’s difficulty saying “no” is also a common problem. Saying “no” can create anxiety, guilt, and in toxic workplaces, retaliation. If you struggle to say “no” and protect your boundaries in the workplace, know you’re not alone. Begin reflecting on your needs and practicing self-advocacy.

And whether or not you struggle expressing your thoughts and feelings, make an effort to make space for others to express theirs. You might be surprised how much morale can change once communication is clear and direct!

What’s your favorite rom com? Let us know your thoughts at ccwomen@cmpteam.com. Love what you see? CCWomen Membership launches in June 2023– we’re offering exclusive content, networking opportunities, live and virtual events, and so much more. Fill out this form to be first in line!