Nine Awkward Dates is a short animated film I created that was featured in two film festivals and was nominated for Best Comedy Film at the Chicago Film Frenzy.
It came about because I said to myself “I want to learn to do hand-drawn animation on an iPad.”
I had done hand-drawn animation in the past, in the ancient times, when you had to draw on paper and take photos of every. Single. Frame. I found myself frustrated with the process, and wanted to see what improvements had been made.
Answer: there were a lot of improvements.
I had used the Apple Pencil and Procreate on the iPad Pro for a few years, learning how rewarding that drawing with a stylus on glass could be. I knew I could make still drawings, but how to make moving ones? Procreate had some functionality with animations, but it was very limited. I wanted something that was close to the hand-drawn-on-paper experience that I had before but with a pure digital-to-digital workflow, and could work with audio well.
I eventually found RoughAnimator, which had a bit of a learning curve but had all the tools I needed. The crucial features it had: onion skinning, a timeline that was easy to work with, frame-by-frame audio monitoring, and solid file exporting.
Once I decided on a program, I decided to do a test animation. I wrote out a short script and had Elevenlabs generate the voices. I made a short animation about a man on a date getting bored and deciding to just make his head explode. I think it may have been inspired by how I felt sometimes on actual dates with people…or maybe I’ve watched Cronenberg films too many times. In any case, the head exploding was a dynamic visual and it was silly. Learned a lot by doing.
Once this was done and I had a finished product, I found myself saying “Can I do this better?” So I did. I got actual humans to record lines, edited them in Adobe Audition, and re-did the animation from scratch, at a 4K resolution.
That turned out pretty well and I guess I could have stopped there, but I did not. Oh no. Too many ideas started swirling in my head about what else I should animate. So I started scripting things out, and very quickly I hit upon the common thread of dating. I wrote thirteen scripts of animated people going on dates and having ridiculous things happen. Some of these were also inspired by real dates and/or a horror film I had seen too many times.
I then looked at what I had planned out and thought “Am I going to do this? Am I going to make thirteen animated shorts now?” The scope of my project had grown very quickly. Also being that actual dating hadn’t gone well for me, I had nobody to tell me not to go too far with this, and I decided that I was just going to see how far I could go with this.
I picked one of my scripts that looked the most compelling to animate and storyboarded it out. So vital for any project is the planning. The storyboards helped me figure out the look for each piece, and how much motion was needed to get from one point to the next. Also, if I couldn’t draw a few still images of a script, I certainly couldn’t draw several hundred to animate it.
I then got a lot of good friends together, skilled performers who were generous with their time to record voices for me. The audio had to be in place before the animation started, because hey, lips need to match the words spoken.
Once all the audio was in place, I got to animating. I had done all the planning so there was an easy scaffolding to follow. Still, it was just a lot of sitting and, drawing frame after frame after frame for months on end. If you were in Chicago in 2024 and saw a crazed man scribbling over and over on an iPad for hours, that was likely me.
As I went, I got better, I learned how to do things more efficiently. I learned what techniques worked for motion and what did not. I got a lot better at matching facial animations to spoken words. I got better at handling a stylus so I didn’t sprain my hand.
It was about the halfway point when I realized that I wanted to pare down my scope. Thirteen was too much. Nine seemed the length where I would have a good variety of animation and be just long enough to be worth watching. I wanted to have it be at least five minutes in length, because that felt like a good length.
Months went by and I kept at the project, with each short getting done giving me a sense of satisfaction and a want to make the next one a little more complicated. I started with only black and white and red with a blank locale for the first animation, and by the last animation, I was doing full-color animations of astronauts on the Moon.
I then took all of the animations and exported them from RoughAnimator into Premiere and Final Cut Pro. From there, I cleaned everything up and decided on running order, with pacing being key. Shorter ones were placed towards the front, to keep you engaged, moving from longer ones toward the end. The longer ones also tended to be the most complex, so in addition to length I’m going to visual complexity.
Eventually I got everything together into a draft form, and it was there I got two big white boards to lay everything out.
I find with any big, complex project it’s always good to see it laid out not digitally, but physically. You can see where the pieces fit more easily spread out on a wall.
I looked for things I wanted to improve, wrote them down, crossed them out as I completed goals. I had a few friends give feedback…I used an AKAI MPK mini in GarageBand to add some closing music, more revisions, more revisions, until I got it to place where I was happy with the final product. Done!
Ah, but what to do with it? I felt that I at the very least, I wanted to have this played before an audience in a theater. I had made the whole thing in 4K, so it was at a resolution for submitting to film festivals.
The festival market in 2025 was pretty saturated, with a lot of people coming off the recent strike in L.A. with a lot of free time on their hands. From what I could gather there was about a 10% acceptance rate for submissions to festivals. I submitted to 15 festivals and managed to get in to 2 festivals so a 13.3% acceptance rate!
I was able to attend the Chicago Film Frenzy, where Nine Awkward Dates was nominated for Best Comedy. It was the first festival it screened in, and the audience response was terrific. People laughed where I wanted them to, and they had a lot of questions about the film during the Q&A. I got to meet many interesting filmmakers and watch a lot of engaging films.
The second festival Nine Awkward Dates was in was the Tucson Undeground Film Festival. I could not attend this, but a friend of mine, Dave Edwards attended, and the film was also well received. He also got some swag.
Now, here in 2026, it’s available for everyone to view.
In the end, I learned a lot about doing hand-animation on an iPad and how to convert it to a digital product to be viewed and well-received by crowds of people. I’m also proud of the result - it’s a film that I feel good about sharing with others not just because I put so much work into it but because I think a lot of the silly jokes work and the visuals are still pretty keen.
It just goes to show that if you want to achieve something, try learning a new skill, then going completely overboard with your scope and spend months and months creating an animated film with heads exploding, monsters destroying cities, and dinosaurs…dining. Plus you get into a few film festivals.
