You're having trouble being funny because you're afraid you aren't. I have an experiment for you. Every time you are in a situation where you find yourself trying to force yourself to be funny, let them win. You're trying to use humor as a way to win at something, to be better than something or somebody, even if it's just yourself. Identify who you're trying to be better than, and let them win. Allow them their victory, and stop playing the game of trying to be more hilarious than they are. This won't make you more funny, but it will make you more relaxed because you don't have to try to meet some goal of humor all the time.
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