If you spend enough time digging through the weirder corners of film history, you're bound to stumble upon something that sounds like a fever dream. That’s exactly what A Date with Diana feels like.
Released way back in 2010 as a digital short—specifically surfacing on the then-massive platform Funny Or Die—this isn't some lost masterpiece of cinema. It’s a parody. A weird, slightly uncomfortable, and surprisingly biting look at what would happen if a regular guy actually tried to take the world’s most powerful Amazonian out for a nice dinner.
People often confuse the title with something more serious. Maybe a documentary about Princess Diana? Or a 1960s classic? Nope. This is about Wonder Woman. And honestly, it’s kinda hilarious how much it leans into the "superhero in the real world" trope before that genre got completely played out by The Boys or Deadpool.
Why A Date With Diana Isn’t Your Typical Rom-Com
Most superhero stories end with the hero flying off into the sunset. They rarely show the part where the hero has to figure out who's paying for the appetizers.
The short stars James Adomian and features Michaela Watkins as Diana. If those names sound familiar, it’s because they’ve been all over the comedy world for years. Adomian is a chameleon of a performer, and Watkins has that specific "I’m smiling but I might kill you" energy that makes this version of Diana Prince actually terrifying.
The premise is simple: James has wanted a date with Diana his entire life. He gets it.
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The reality? It’s a disaster.
The "Super" Personality Problem
In this version, Diana isn't the benevolent diplomat we see in the Gal Gadot movies. She’s intense. She’s judgmental. She’s basically a god who has zero patience for mortal nonsense like "checking the menu" or "making small talk."
- The Power Dynamic: Imagine trying to order a glass of house red while your date is talking about the fall of man and the glory of Themyscira.
- The Lasso: Yes, the Golden Lasso makes an appearance. No, it isn't used for anything heroic.
The comedy comes from the total lack of chemistry. James is trying to have a "human" moment, while Diana is operating on a plane of existence that involves ancient Greek deities and constant combat readiness. It’s the ultimate "never meet your heroes" cautionary tale.
The Cultural Context of 2010
To understand why this short even exists, you have to remember what was happening in 2010.
The Marvel Cinematic Universe was barely a toddler. Iron Man 2 had just come out. DC was still trying to figure out what to do after The Dark Knight. Wonder Woman hadn't had a live-action hit since Lynda Carter left the airwaves in 1979.
We were in this weird limbo where superheroes were becoming cool again, but we hadn't yet reached the point where they were everywhere. A Date with Diana filled a gap. It mocked the reverence we have for these characters.
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Funny Or Die was at its peak during this era. They were churning out high-production-value sketches with actual celebrities. Seeing a legitimate take on the Wonder Woman costume in a comedy sketch felt like a big deal back then.
Common Misconceptions About the Project
I see people searching for this all the time thinking it’s a "lost" 1961 film or a documentary. Let's clear some of that up right now.
Is it a documentary about Princess Diana?
No. While there are countless films about Lady Di, this isn't one of them. If you’re looking for a deep dive into the British Royal Family, you’re in the wrong place. This Diana wears a tiara, but it’s for deflective purposes, not just for show.
Was there a 1961 version?
This is where it gets confusing for the Google algorithm. There was a film in 1961 called On the Double starring Diana Dors and Danny Kaye. Because Diana Dors was a massive star (often called the British Marilyn Monroe), people sometimes link "A Date with Diana" to her. But no, the 2010 short is its own beast.
The "Veronica Cale" Connection
In the actual DC Comics, specifically Wonder Woman #22 (the Rebirth era), there is a storyline where a character named Veronica Cale bids $15 million at a charity auction just to go on a date with Diana. That’s a real thing that happened in the books. Fans of the comic often search for "A Date with Diana" looking for that specific arc, but the 2010 short is a parody of the concept of dating her, not an adaptation of that comic.
What This Short Teaches Us About Modern Fandom
Honestly, looking back at it now, the sketch was ahead of its time.
We’ve become obsessed with the "grounded" superhero. We want to know what they eat, how they sleep, and who they date. A Date with Diana suggests that we actually don't want to know.
If superheroes were real, they would be exhausting. They would be narcissistic. They would probably be terrible at dating because their entire lives are centered around their own legendary status.
Key Lessons from the Sketch:
- Don’t date an immortal. Their perspective on time is just too different. Five minutes to you is a blink of an eye to them; they’re never going to be on time for dinner.
- The Lasso of Truth is a relationship killer. Imagine being on a first date and being physically incapable of lying about whether you liked her outfit or if you’re still thinking about your ex.
- Appreciate the myth, avoid the person. Some icons are better left on the pedestal.
Actionable Takeaways for Movie Buffs
If you’re trying to find this or similar content, you need to know where to look.
First, go to the archives of Funny Or Die. A lot of their 2010-era content is still hosted there or on their YouTube channel. It’s a time capsule of early-internet comedy.
Second, if you’re actually interested in the real dynamics of Diana Prince’s dating life, skip the parody and go straight to the Greg Rucka run of Wonder Woman comics. He handles the "human" side of the character better than anyone else in the industry.
Lastly, if you're a filmmaker, take a page out of the Adomian/Watkins book. The reason this short worked isn't because of the special effects—it’s because of the character work. They took a goddess and made her a "bad date," which is a relatable human experience.
Check the credits next time you watch a "lost" short. You might find that the "indie film" you're looking for was actually a viral sketch from fifteen years ago.
- Watch the 2010 short on Funny Or Die for a 4-minute masterclass in character parody.
- Read Wonder Woman (Rebirth) #22 if you want the high-stakes, $15 million charity date version of the story.
- Search for James Adomian’s other work if you like that specific brand of high-energy, transformative comedy.