I could also see the women reacting really differently too. Like Regina would take it personally if the girl rejected Henry, Emma would tell him to follow his gut and just leave him to figure it out on his own, Belle would give him a library’s worth of romance novels and tell him to read them, and Snow would be really meddlesome and try to have a word with the girl (probably causing more problems than solutions).
The more I think about it the more I feel we need this to happen, especially since we haven’t gotten too much of Henry this season.
I hadn’t really given much thought to how the females in Henry’s life would react to him having a crush on a girl and what kind of advice they would give him. I can see this being the case though.