Hey there! My game is a bit unlike most dating sims, and tries to use a bit more of a realistic setting and style of relationships.
Syd (the protagonist) CAN date Maisy. Eventually. But not right off the bat, it's a relationship the player has to build to the point in which they can start dating. Syd can definitely flirt and get Maisy to like him though. You'll know if you did well if Maisy acts extra jealous or clingy with Syd and if at the end the "results" screen say she is growing feelings for the player and losing them for her "current boyfriend."
Thanks for the question, and let me know if you need any more clarification.