Simple story, but with a lot of possibilities. Write a good dialogue (not too many words), make the order a little love story. He instantly falls in love with her, which makes his frustration even more funny and gives him a better motivation to learn intensively. Keep the learning sequence short, you could superimpose floating english words that fade in and out. His ambition could be funny again. When the day comes, he is surprised (as she is and we are) that he asks her to have coffee with him (or something more witty, english is not my native language). Happy end, a classic.
For a beginner, it's perhaps best not to move the camera too much. Find a classic, conservative framing, capture clean dialogue (use at least a good directional mike, mono), you better mix atmo and music in post.
Biggest challenge is direction. Wise directors said, there is no bad acting, only bad directing. Meaning: Don't teach your talents how to act. Take your time. Change the script, change the story on set. Don't rehearse, just start over with the changes. Tailor dialogue and action so that your character fits to the actor, never conversely. Don't cut a dialogue scene into one-sentence-takes during the shoot. Repeat the scene in complete length from other POVs. Let them repeat often. Don't praise or criticize too much. Stay serious and NEVER lose your nerve. Cater (softdrinks, coffee and sandwiches, don't start with beer and pizza, both demoralize).
Overacting is not funny. It's the situation that must be funny.
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