Tifa is the best choice. Cloud is second place.

(I also REALLY love Tifa’s outfit here.)

You know what really annoys me about this?

I’ve played FF7 a bunch and I still can’t remember which one the don chooses

The Don’s choice depends on what outfits/accessories you manage to get.

If you get the worst options, he goes for Tifa. If you do okay, he chooses Aerith. If you get the best stuff, he chooses Cloud.