AWM Staff Picks: Favorite Rom-Coms

Before Sunrise (1995)
screenplay by Kim Krizan and Richard Linklater

The first in director Richard Linklater’s Before series (including sequels Before Sunset and Before Midnight) it stars Ethan Hawke as American Jesse and Julie Delpy as Parisian Celine. The pair of gorgeous 20-somethings meet on a train and then spend the entire night talking and walking the streets of Vienna. It’s beautifully filmed, light in tone, and utterly charming thanks to the effortless performances of its leads. There’s no wacky hijinks or frustrating misunderstandings keeping the couple apart—only the very real, looming question of what happens in the morning when Jesse has to get on a plane. (And yes, that’s Maya Hawke’s dad).

—Annie, Administrative Associate

Bewitched (2005)
screenplay by Delia Ephron and Nora Ephron

In a world of heartless remakes of classic TV shows, we need more movies about someone making a movie adaptation of a classic TV show. Genuinely, this is one of my favorite films and my favorite rom-com. Nicole Kidman is, as always, an absolute delight. This film is perfect for shutting off your brain and enjoying some romance and comedy.

—Matt, Community Engagement Manager

Cold Feet (1983)
screenplay by Bruce Van Dusen

I’m not a huge fan of the romantic comedy genre but Cold Feet makes me feel squishy inside. It’s an indie film from 1983 starring Griffin Dunne as his most awkward and endearing self as he, fresh out of a marriage, warily begins a friendship with an equally cautious, newly single woman. This is not a smooth film. It’s low budget, quirky and jerky—you can even see the microphone boom in some scenes! But Cold Feet has great heart and humor, and a terrific soundtrack by Todd Rundgren. The ending makes my heart soar.

—Carol, Assistant Director of Development

Crazy, Stupid, Love (2011)
screenplay by Dan Fogelman

Genuinely, this is one of my favorite movies. What I would GIVE to rewatch the scene in the backyard for the first time. Truly the perfect rom-com.

—Maya, Marketing & Creative Associate

Dirty Dancing (1987)
screenplay by Eleanor Bergstein

Dirty Dancing effortlessly blends classic rom-com tropes with music, dance, and even more serious themes like class and women’s reproductive rights. It is a lesser-known fact that Dirty Dancing is also a strong example of Jewish representation. In writing the screenplay, Bergstein drew on her experience vacationing with her family at a Jewish resort in the Catskill Mountains, a region of New York State nicknamed “The Borscht Belt.” During the 1950s, 60s, and 70s (Dirty Dancing notably takes place in the summer of ’63), the Borscht Belt was the most popular vacation destination for Jewish families, known for live entertainment and organized activities. Dirty Dancing is a glimpse into this historical part of American-Jewish culture.

Fever Pitch (2005)
screenplay by Lowell Ganz and Babaloo Mandel

Ben and Lindsey’s relationship is going great…until baseball season starts, and Ben’s obsession with the Boston Red Sox threatens to tear them apart. As a sports fan myself, I appreciate a baseball-themed rom-com, and I also can admit that I found myself relating to both Lindsey and Ben throughout the movie too. (Who among us would not be a tiny bit sad if they missed a historic game involving their favorite team? Just saying). This movie also offers a quote that is personally poignant: “You love the Sox, but have they ever loved you back?”

—Courtney, Assistant Director of Education

50 First Dates (2004)
screenplay by George Wing

What I love most about this rom-com is that there is not the normal formula of why things do not work. There is this amazing challenge for all the people involved in the love story, from her family and friends, to deal with tragedy in a way that keeps someone safe or to risk change for the opportunity at love. In the end there is not a pure happily ever after, but rather the notion that to make a long lasting love, they choose to start over working on that love story every day, over and over.

—Carey, President

Forgetting Sarah Marshall (2008)
screenplay by Jason Segel

Forgetting Sarah Marshall embraces the humor and sentimentality of the rom-com genre. Jason Segel stars in the film and wrote the screenplay, heightening the authenticity and witty flow of the dialogue. This movie has been one of my favorite rom-coms since a late-night viewing with my family while on vacation in Florida. The tropical setting of Forgetting Sarah Marshall (Hawaii) elicits feelings of a fun, vacation-y romp, and Segel’s writing puts a quirky spin on typical genre conventions. It seems absurd that, for example, the protagonist’s dream is to write a Dracula puppet rock opera. But within that absurdity, Peter Bretter (Segel) is so lovable that his dreams feel believable.

—Sydney, Systems Operations Coordinator

Grosse Pointe Blank (1997)
screenplay by John Cusack, D.V. DeVincentis, Tom Jankiewicz, and Steve Pink

This is a romantic comedy designed as a crime comedy. John Cusack stars as Martin Blank, a professional hitman who returns to his hometown of Grosse Pointe, Michigan, for a job and also his 10-year high school reunion. Minnie Driver stars as the high school sweetheart he stood up at prom. Dan Aykroyd, Joan Cusack, Jeremy Piven, and Hank Azaria round out the cast, and the score was performed by Joe Strummer of The Clash. John Cusack gives a great doe-eyed performance as a hitman wrestling with his conscience. The pace is breezy, the dialogue snappy, the soundtrack on point.

—Annie, Administrative Associate

Harold and Maude (1971)
screenplay by Colin Higgins

I first watched this film in college in a class that was required for my “Sports Studies” minor. As you might guess, the minor ended up being less about sports and more about…whatever this is about. This film has stayed with me, with its dark humor and unconventional romantic relationship. It reminds me that love can take many forms and that society’s version of “conventional” love may often fall short. In fact, there are two ducks that return to nest at the same place in my parents’ backyard every year. We have come to call them Harold and Maude.

My partner added a few thoughts of her own for this film, which is one of seven she owns on DVD. And I quote: “Timeless nostalgia. Comedy gold. Satire. The soundtrack is fantastic. Plus it’s f***ing weird. It’s got a little bit of everything and it makes me want to cry.”

—Nate, Content & Exhibits Manager

Leap Year (2010)
screenplay by Harry Elfont and Deborah Kaplan

Includes the classic trope of “there’s only one bed at the inn for two people to share”…that alone is enough, but Matthew Goode’s painfully charming a**hole bit is the cherry on top.

—Maya, Marketing & Creative Associate

Morning Glory (2010)
screenplay by Aline Brosh McKenna

It’s a love story where the primary relationship—including a meet-cute, grand romantic gestures, a misunderstanding that results in a woman running across New York City in heels—isn’t a romance but a platonic mentor-apprentice bond between Rachel McAdams’ morning TV producer and Harrison Ford’s grizzled veteran newsman. The love these two journalism freaks develop over the course of 90 hilarious minutes is more real than most wedding scenes.

—Allison, Director of Programs

My Big Fat Greek Wedding (2002)
screenplay by Nia Vardalos

Even if you are not Greek yourself, I think My Big Fat Greek Wedding is a very relatable movie. Even though you love your family, sometimes your family also can have quirks that are overwhelming or embarrassing at times, which can also make introducing your new partner to them very interesting! I also think My Big Fat Greek Wedding depicts the challenges that can occur when you are bringing families from different cultural backgrounds together in a humorous but loving way. This movie is also insanely quotable. It is one that my parents and I loved to watch together, and my dad and I will still quote this movie to each other when we can.

—Courtney, Assistant Director of Education

People We Meet on Vacation (2026)
screenplay by Yulin Kuang, Nunzio Randazzo, and Amos Vernon

The movie adaptation of Emily Henry’s book published in 2021. While the book remains better, in my opinion, the performances by the main actors have you laughing and crying the whole time. It is also very exciting to see books that you loved being brought to the big screen.

—Andrea, Education Program Coordinator

The Princess Bride (1987)
screenplay by William Goldman

Quite possibly the very best movie ever made. This one has—and I quote—”Fencing, fighting, torture, revenge, giants, monsters, chases, escapes, true love, miracles.” Cary Elwes is Westley the Farmboy-slash-Man in Black, and Robin Wright is Buttercup, the titular princess bride. Directed by the late Rob Reiner, this movie is stuffed with memorable characters and quotable lines—like this one: “Death cannot stop true love. All it can do is delay it for a while.”

—Annie, Administrative Associate

Red, White & Royal Blue (2023)
screenplay by Matthew López and Ted Malawer

Based on the book by Casey McQuiston, Red, White, & Royal Blue is the heartwarming love story of the first son of the United States and an English prince. This is a fantastic, sexy little film and I can’t wait for the sequel to come out next year.

—Matt, Community Engagement Manager

Set It Up (2018)
screenplay by Katie Silberman

It is a shame that they haven’t put Glen Powell and Zoey Deutch in more movies together, because their on-screen chemistry is amazing! As someone on Rotten Tomatoes said, this is comfort food in movie form, and it never fails to make me laugh and smile. The main characters are very likeable, the soundtrack is fun and the plot is something we hadn’t seen before. Definitely one of the first movies I show to people when I am sharing my love for rom-coms. Also, fun fact, the director Claire Scanlon is a Chicago native!

—Andrea, Education Program Coordinator

She’s All That (1999)
screenplay by R. Lee Fleming Jr.

A movie I love despite it being predictable and of middling quality at best. It’s based on the play Pygmalion by George Bernard Shaw and the movie My Fair Lady based on the aforementioned play. So, it’s sort of doubly unoriginal. Audiences will know and love it for:
1) Being the movie that the Sixpence None the Richer song “Kiss Me” was in
2) Being one of the best examples of the cliche where the unpopular girl takes off her glasses and she suddenly “becomes” beautiful, and
3) Being a movie that has Clea DuVall in it.

—Cassidy, Guest Services Manager

10 Things I Hate About You (1999)
screenplay by Karen McCullah Lutz and Kirsten Smith

You can never go wrong with one of the classic tropes: enemies to lovers. The soundtrack and performances fully sell you on the movie, and I love how writing is included as a tool to help move the plot. Also, no spoiler, interesting to see how fanfiction was already a thing back then. Additionally, this movie is a modern adaptation of Shakespeare’s The Taming of the Shrew.

—Andrea, Education Program Coordinator

Tonight You’re Mine (2011)
screenplay by Thomas Leveritt

Maybe it’s not a cinematic masterpiece, but its unconventional filming (shot live at the music festival T in the Park in Scotland) makes it unlike most movies I’ve seen before. Makes me feel cozy and happy, which I think is the best part of any rom-com.

—Maya, Marketing & Creative Associate

When Harry Met Sally (1989)
screenplay by Nora Ephron

A gold standard of rom-coms, sure to land on every reviewer’s list. Written by Nora Ephron and directed by (again) Rob Reiner, the film stars Billy Crystal and Meg Ryan as the titular couple and poses the question, can men and women actually be friends? The performances are legendary, the dialogue sparkling, the quotes are endless. I have used the phrase, “You’re right, you’re right, I know you’re right” so often in real life I forget it’s from Carrie Fisher.
—Annie, Administrative Associate

When Harry Met Sally is my favorite rom-com of all time. Its humor is actually laugh-out-loud witty, delightfully snarky, and sprinkled with astute observations about human nature and falling in love. This is an annual rewatch for me, and an autumnal reminder that true love is sometimes slow, but endlessly worth it. Idiots to lovers forever.
—Sydney, Systems Operations Coordinator

While You Were Sleeping (1995)
screenplay by Fred Lebow and Daniel G. Sullivan

This 90s rom-com was filmed in Chicago! In winter! On the CTA! The city is beautifully highlighted with scenes from Lake Point Tower, northwest side bungalows, bridges over the river, and Logan Square courtyard apartments. Let’s move past the fact that Sandra Bullock’s character lies to an entire family about her made-up relationship with the comatose Peter Gallagher. It leads her to hunky antique furniture wheeler and dealer Bill Pullman. But who will she choose? A charming narrative with visuals to match. What’s not to love?
—Andrew, Institutional Giving Manager

The plot for While You Were Sleeping is admittedly wacky and far-fetched, but this has always been one of my favorite movies. You do have the standard “two-people-falling-in-love” storyline between Lucy and Jack, but there is also the “love” story between Lucy being accepted and welcomed into the Callagan family, which warms my heart every time I watch. The characters are all so charming, funny, and endearing that it is hard not to fall in love with everyone.
—Courtney, Assistant Director of Education

Zack and Miri Make a Porno (2008)
screenplay by Kevin Smith

Hear me out on this one. Seth Rogen and Elizabeth Banks star as very broke friends and roommates who decide to make an adult film in order to get the lights turned back on in director Kevin Smith’s extremely raunchy romantic comedy. Things get a little too real when they have to, ah, film the big scene and end up catching feelings. The film works because the actors are damn good and the script is just funny. Even Roger Ebert gave it three stars.

—Annie, Administrative Associate