I smell a misunderstanding. She should just talk with Ian if she thinks he likes Stella, he would love to hear it. Or if that scares her independently confirm it from a friend she can actually trust, like the student council VP.
The strawberries thing is a really weird conversation. This is an alternate reality and all, but strawberries are incredibly easy to grow (though hard work) and a mainstay of peasant gardens. Grown in gardens they are generally smaller and much less mushy, and I have no idea how Stella could eat an old strawberry when people would only ever eat them off the vine. It could be a sign that Stella is deliberately trying to play up her ignorance and poverty, or more likely the author just didn't do their homework.
@ichigodream speaking of which, what happened to that dress? It just disappeared after Stella got it.