The Matchmaker's Error is my entry for ONC 2025.

Hosted by Open Novella Contest

The Prompt:
113. Your sister won't stop talking about her crush, so you, fed up, ask the boy she's in love with to start dating her. The problem? He has no idea how to ask her out and turns to you for help. Before you know it, you're playing matchmaker for the two of them - how much longer can you be their cupid?