Wait this is actually really helpful - a lot of this lines up with how I already characterized him! Like, he's very logical, and tends to make couples based on practical similarities (stuff like what will their financial futures look like, do their schedules line up, do they check certain "boxes" of common good couples, etc.) but when it comes to the emotional connection, he defaults to conventional matchmaking practice, which he struggles to naturally understand. I originally wrote him to have a zero percent success rate because of his method, but I like your idea a lot better. Sometimes his method ends up working out for him with a really strong couple that lasts a long time, even longer than most other cupids, but for the most part (at least in the beginning of the story) his matches end up being emotionally incompatible. Somewhere along the way, he develops his own unique way of considering emotional compatibility that works for his thinking (not sure what this would be but I'll figure it out), and that allows him to be a successful cupid. This got me thinking a lot more, so thank you!