>>5663586Literally nothing wrong with that, as
>>5664574 said, you don't need to make your oshi laugh for her to appreciate your message. It's up to YOU if you're comformable with that, or if your objective is getting a reaction out of them.
And it's with regret that I must inform you that not only it takes time to be able to make silly, situation-related, jokes, it's also something you're kind of born with.
It's never late, one way to improve your funny commentaries is by observing commedians (not stand up, I'm talking more in line with Map Men) and imitating them, you'll gradually understand and grasp what makes a funny comment, funny.