It starts with a question. A kid asking her dad how he met her mom, but with a twist—he changes the names. That’s how the Definitely Maybe film trailer hooked us back in late 2007. It wasn't just another romantic comedy preview. Honestly, it felt like a mystery wrapped in a sweater vest. Ryan Reynolds was at that specific career pivot point where he was transitioning from the "Van Wilder" guy into a genuine leading man who could actually carry a dramatic beat.
You remember the music, right? That upbeat, slightly indie-pop vibe that defined the mid-2000s cinema experience. The trailer used "Everyday" by Rogue Wave and "The Air Itself" by The Language of Flowers. It set a mood. It wasn't just about "who is the mom?" It was about the messy, non-linear way people actually fall in love—or out of it.
Watching it now, the Definitely Maybe film trailer is basically a museum of 90s nostalgia seen through a 2008 lens. We see Will Hayes (Reynolds) arriving in New York City in 1992 to work on the Clinton campaign. It’s all pagers, landlines, and those chunky block cell phones. The trailer does this clever thing where it balances three very different women—Elizabeth Banks, Isla Fisher, and Rachel Weisz—without making it feel like a cheap dating game. It promised a story about growth, not just a punchline.
What the Definitely Maybe film trailer gets right about storytelling
Most rom-com trailers give away the ending. You know exactly who ends up together by the time the two-minute clip hits the one-minute mark. But this one? It played its cards close to the vest. It focused on the chemistry between Reynolds and a young Abigail Breslin. Their father-daughter banter was the anchor. Breslin was fresh off her Little Miss Sunshine Oscar nomination, and the trailer leaned hard into her ability to be "precocious but not annoying."
It’s a tricky balance.
The editing jumps between 1992, 1994, 1997, and the "present day" of 2008. Usually, that’s a recipe for a confusing mess. Yet, the Definitely Maybe film trailer managed to signal these time jumps through hair styles and political posters. You see the transition from idealistic youth to cynical adulthood in about ninety seconds. It's impressive. People often forget that this was a Working Title production. Those are the same people behind Love Actually and Notting Hill. They know how to cut a trailer that tugs at the heartstrings without being totally cloying.
There’s a specific shot of Isla Fisher’s character, April, in a copy shop. It’s such a small moment, but the trailer highlights it because it captures that specific 90s "slacker" energy. It wasn't just selling a movie; it was selling a vibe of a New York that doesn't really exist anymore.
The music choice was everything
If you listen closely to the Definitely Maybe film trailer, the soundscape evolves. It starts with the whimsical curiosity of a child’s bedroom and swells into the orchestral sweep of a "big" cinematic romance. But it stays grounded. Using Rogue Wave was a masterstroke. It gave the film an "indie" credibility that separated it from the more corporate-feeling rom-coms of the era like 27 Dresses or How to Lose a Guy in 10 Days.
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It’s about the stakes. The trailer makes the stakes feel personal. It’s not about saving the world or winning a bet. It’s about a guy trying to explain his failures to his daughter so she doesn't make the same mistakes. That’s heavy stuff for a movie marketed with a "Definitely, Maybe" title.
Why we still talk about this specific preview
Context matters. In 2008, we were at the tail end of the DVD era. Trailers were things we watched on Apple.com/trailers in QuickTime player. The Definitely Maybe film trailer was a staple there. It represented a shift toward "smart" romantic comedies.
Think about the competition.
At the time, the genre was getting a bit stale. We had a lot of "high concept" plots. This trailer promised something grounded in political history and genuine character arcs. It showed Will Hayes as a flawed human. He smokes. He drinks. He gets his heart broken. He breaks hearts. The trailer didn't shy away from the fact that he might actually be the "bad guy" in some of these stories.
Also, can we talk about the cast? This might be one of the best-cast films of the 2000s.
- Ryan Reynolds: Pre-Deadpool, showing his range.
- Rachel Weisz: Bringing "serious actress" energy to a summer-feeling flick.
- Isla Fisher: Proving she was more than just the "crazy girl" from Wedding Crashers.
- Elizabeth Banks: Capturing that "college sweetheart" nostalgia perfectly.
The Definitely Maybe film trailer introduced all four of them as distinct pillars of Will’s life. You weren't just rooting for one; you were intrigued by all of them. That is incredibly hard to do in a short promotional video.
The "Mystery Mom" Hook
The trailer basically turned a romantic comedy into a whodunit. By labeling the women as "Emily," "April," and "Summer," it invited the audience to play along. It was interactive before everything was "interactive." You'd talk about it at the water cooler—or, well, on early Facebook. "I think it's the one in the copy shop," people would say. The trailer was the catalyst for that debate.
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The technical side of the Definitely Maybe film trailer
From a technical standpoint, the color grading in the trailer is fascinating. The 90s scenes have this warm, amber, almost hazy glow. It looks like a memory. The "present day" scenes with Maya (Breslin) are cooler, crisper, and more clinical. This visual shorthand tells the viewer exactly where they are in the timeline without needing a "1992" title card every five seconds.
The pacing is also erratic in a good way. It starts slow—the bedtime story. Then it speeds up as Will’s life gets complicated. The music swells, the cuts get faster, the dialogue gets snappier. Then, right at the end, it slows down again for a quiet moment between father and daughter.
"Did you live happily ever after?" she asks.
"I'm working on it," he says.
That’s a killer closing line for a trailer. It’s the "hook" that stays with you. It’s not a spoiler, but it’s an emotional promise.
Lessons for modern content creators
If you’re looking at the Definitely Maybe film trailer today, there are some genuine takeaways for how to tell a story in a short amount of time.
First, lead with empathy. We care about Will because we see him through his daughter’s eyes.
Second, use "Easter eggs." The trailer is full of 90s references—the Clinton/Gore signs, the fashion—that reward people for paying attention.
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Third, don’t be afraid of silence. Some of the best parts of the trailer are the pauses. In an era where every YouTube ad is screaming for your attention in the first three seconds, the restraint shown in this 2008 preview is actually quite refreshing.
It’s also a reminder that Ryan Reynolds has always been great at being vulnerable on screen. We see the "Deadpool" wit in the trailer, sure, but we also see the guy who is genuinely lost. That’s the version of Reynolds that made him a star.
Final thoughts on the Definitely Maybe film trailer legacy
Watching the Definitely Maybe film trailer now feels like looking at a lost art form. The mid-budget rom-com has largely moved to streaming services, where the trailers often feel generic and "algorithmic." This trailer had a soul. It felt like it was made by people who loved the story, not just a marketing department trying to hit a demographic.
It’s a masterclass in tone. It manages to be funny, sad, nostalgic, and hopeful all at once. If you’re a fan of the film, the trailer is a great reminder of why you fell in love with it in the first place. If you haven't seen it, the trailer is the perfect entry point.
To get the most out of this nostalgia trip, go back and watch the trailer on a high-quality platform. Pay attention to how the music shifts between the different decades. Notice the small costume changes that signal Will's aging. Most importantly, look at how the trailer uses Maya (the daughter) as the surrogate for the audience. She's asking the questions we want to ask. That’s how you build a connection.
If you're looking to analyze film marketing, start here:
- Track the tonal shifts: How does it go from "funny dad" to "heartbroken young man"?
- Analyze the color palette: Look for the transition from the amber 90s to the blue 2000s.
- Listen to the lyrics: The songs aren't just background noise; they mirror the plot.
- Watch the eyes: Ryan Reynolds does a lot of acting with just his expressions in this cut.
The Definitely Maybe film trailer isn't just a commercial; it’s a short film in its own right that perfectly captures the "maybe" of life.