This may be the most obvious cue that your crush likes you. Of course, assuming that you’re not too close, popping up a question about your past may seem too personal but he wouldn’t mind that.
This indicates that he’s making an attempt to know if you’re single, interested with others or you’re over with your past relationship. After this, he might insert some questions about your ideal guy and might evaluate himself if he is. But this doesn’t happen always, some guys would just make an attempt to set you up with others.