Sometimes a movie arrives at exactly the right moment in your life—or, in this case, returns to you when you’re finally ready for it. That’s what happened when I revisited 27 Dresses.

Jane Nichols (Katherine Heigl) has been a bridesmaid 27 times, always putting others first while neglecting her own happiness. During a hectic night attending two weddings, she meets cynical journalist Kevin Doyle (James Marsden), who is intrigued by her devotion to romance. When Jane accidentally leaves behind her planner, Kevin uses it to research her for a potential story, writing under a pseudonym while hiding his true intentions.

Jane’s younger sister Tess (Malin Åkerman) returns home and quickly becomes engaged to Jane’s boss George (Edward Burns), whom Jane secretly loves. Despite her heartbreak, Jane agrees to plan the wedding. As Kevin covers the engagement for his Commitments column in the New York Journal, he grows closer to Jane, especially after she reveals her collection of bridesmaid dresses. However, when his article is published without her knowledge, Jane feels betrayed and cuts him off.

Tess’s lies eventually unravel, leading to a public fallout that ends her engagement to George. Encouraged to reevaluate her own life, Jane leaves her job at Urban Everest and realizes her feelings for George have faded. She instead follows her heart, seeking out Kevin and confessing her love. A year later, the two marry, with all 27 brides Jane once supported returning the favor as her bridesmaids.

When I went into my rewatch of 27 Dresses in late March, I was not expecting to enjoy it as much as I did. I remembered liking the film the first time in 2008 and loving the bar scene where they launch into a rendition of “Bennie and the Jets.” But no, I wasn’t expecting the film to have me sucked in and fully engaged from start to finish. Conventional rom-com tropes—whether they’ve aged well or not—be darned, this film left an imprint on me when I first saw it, leading it to work for me on every level all these years later, and I loved every minute of it.

It didn’t matter to me that Jane had sacrificed her own life to always help her friends with their weddings. Hell, she has 27 bridesmaid dresses hanging up in her closet to prove it. She might love being a bridesmaid a bit too much, and yet Heigl is perfect in the role. I never watched Grey’s Anatomy, so my first real introduction to her had been in Knocked Up. However, 27 Dresses allows the actress to show her comedy chops in a way that the Judd Apatow film never could and allows her to play a character that is funny, charming, and flawed.

As Kevin points out in 27 Dresses, Jane has a problem saying no. Is this why she’s been stuck working as an assistant to George for the better part of ten years and why she keeps being part of the bridal party? Possibly. It’s through her blooming relationship with Kevin that she learns things about herself and ultimately leads to her 28th dress at the end of the film. At the same time, I can understand Jane not having had a boyfriend (not even a +1 to all these weddings) because I’ve never been in a relationship. Even now, it feels somewhat scary to put myself out there despite knowing what I want.

There’s something about love, whether it be the feeling of being wanted or just the mere act of falling in love with someone else. I’ve never had that—not in the traditional sense anyway—so most of my experiences come through watching straight romances in movies. Whether it’s healthy or not, I don’t care. Because of societal expectations, I learned at a young age to bury my feelings deep down, and even then, it still wasn’t enough to stop the teasing at school during a time that was decades before coming out. Any feelings that I’ve ever had for a guy were buried so far down that I suppressed them for years.

That’s not the only thing. There was something I realized about myself in the hours before pressing play on 27 Dresses. I admitted to myself that romantic comedies are my favorite genre of movies. It came as a surprise to me, being someone who generally rewatches a number of MCU films for comfort. But if I’m not rewatching Jurassic Park/World or Marvel movies for comfort, I’m turning to films like Airplane!, The Naked Gun, Dr. Strangelove, and Home Alone whenever I try to kick a depression. And then there are the classic films starring Cary Grant that I really need to be in the right mood to watch: The Philadelphia Story, Bringing Up Baby, His Girl Friday, and Charade.

I’m not ashamed to admit that rom-coms hit me in a way that’s deeper than just being entertainment. Watching these movies is about something else: connection, desire, emotional rhythm, and just as important, a sense of belonging. When I watch these films, I feel that I belong. Watching 27 Dresses provides a level of emotional recognition that speaks in a language that both my brain and body understand. And when I watched it for only the second time in my life, I had feelings that I never wanted to end. It’s one thing to have scene-specific emotions, but it’s another to experience something for the entire runtime.

What 27 Dresses provided for me when I watched it was romance and an emotional payoff when I was in the right mood for it. Then there’s the comfort loop that comes with rom-coms and knowing what’s likely to happen because of the genre tropes. And then there’s the part I can’t explain: 27 Dresses is connected to my identity and memory in a way that I don’t know if I’ll ever be able to fully understand, but I love who and what I become whenever I think of the film. It’s a feeling that I’ve never felt for other films, not even the aforementioned comfort rewatches.

The other thing about 27 Dresses is that I’m not usually invited to non-family weddings. If you don’t include the one invitation that got lost in the mail in 2009, I’ve only ever been invited to three weddings of non-family members—two came during the pandemic. The first bachelorette party I was ever invited to was also canceled because of the pandemic. When you hear several friends talking about going to the same wedding, there is a serious feeling of being left out. I try not to take it personally, but it still hurts. Obviously, people can only invite so many people to their wedding, but there’s a large part of me that wonders if it’s because I’m trans.

So yeah, watching 27 Dresses enabled me to live vicariously through Jane, going from wedding to wedding or planning her sister’s wedding before sabotaging it. All the romantic longing and aspirations relating to weddings? I got to experience that through 27 Dresses more so than real life. Say what you will about Jane, but the foundation of any relationship should never be built on lies (I’m looking at you, Tess), and that’s before taking her crush on George into account. And when they finally kiss, there’s nothing there between them because Jane’s real feelings have been for Kevin all this time. You can’t help but smile.

James Marsden has a history of starring in movies where he ends up on the short end of the stick in love triangles. This time, he finally gets the girl. As for Judy Greer, the film could have just leaned on her for comic relief as Jane’s “crazy best friend,” but there’s more to her than that.

Screenwriter Aline Brosh McKenna explores the idea of people-pleasing through the guise of a bridesmaid. It just so happens that Jane wants to be everything to everyone, which is how she ended up being a bridesmaid in over two dozen weddings. A number of the dresses are not the best-looking, but that’s intentional by design. If a dress was ugly or over the top, they pushed it even further. What may be most surprising is just how many dresses costume designer Catherine Marie Thomas found in the real world. As far as the comedic banter goes, 27 Dresses has a back-and-forth rhythm on the same level as the classic comedies starring Cary Grant and Katharine Hepburn.

As a film, 27 Dresses is more character-driven, but it’s more than just a film about two people on a poster running into obstacle after obstacle on their way to falling in love. There are real characters that we get to meet in the film, and that’s what helps prevent it from being just another rom-com.

While 27 Dresses is set in New York, the bulk of the filming took place in Rhode Island. Shepherd Frankel did a stupendous job designing the weddings seen on screen. As for Jane’s apartment, it’s a character in and of itself. He gives Urban Everest something of an eco-friendly design. Hal’s Hardware and Tools was a practical location rather than being designed from the ground up on a soundstage.

Here I am in 2026, owning the fact that I love rom-coms and being unapologetic in how much I love this film. It’s not just the fact that 27 Dresses may have become my favorite romantic comedy of all time, but it’s perhaps the only film that is in full alignment with my sense of romance, femininity, and attraction. This film did something for me when I was 23, but I didn’t realize the emotional imprint that it left on me until it triggered something during my rewatch. No other film has been able to connect with my emotional wiring in this way: 27 Dresses became a touchstone for my romantic and emotional self.

DIRECTOR: Anne Fletcher
SCREENWRITER: Aline Brosh McKenna
CAST: Katherine Heigl, James Marsden, Malin Åkerman, Judy Greer, Melora Hardin, Brian Kerwin, Maulik Pancholy, David Castro, Krysten Ritter, and Edward Burns

Fox 2000 released 27 Dresses in theaters on January 18, 2008. Grade: 5/5

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