I'm totally blanking on if they have multiple endings but I love Digital: A Love Story and If Found. I also liked We Know The Devil and A Summer's End - Hong Kong 1986, which do have multiple endings, but are a little more adult. All are fairly short. Ladykiller in a Bind is more comedic since you're looking for something along those lines and each playthrough is fairly short although that has more player input than the other games I mentioned.
this post was submitted on 17 Jun 2023
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Adventure / Point-and-Click / Narrative Games
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Those are my favorite ones.
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Raging Loop
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Yu-No
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AI: The Somnium Files
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Zero Escape trilogy
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Danganronpa trilogy
Most don't really have multiple endings, but some of those titles have a story branching mechanic that might be of you interest.
Edit: Here's a visual novel database if you are interested. This is the same site with the multiple endings tag applied.