We tried to solve a similar problem with our app, too. We were trying to generate questions based on person and occasion (think: "What should I get my boyfriend

We tried to solve a similar problem with our app, too. We were trying to generate questions based on person and occasion (think: "What should I get my boyfriend for his birthday). It got interesting when occasions didn't warrant possessives ("What should I get my boyfriend for Christmas"), and when language factors were considered ("What should I get mi abuelo for su cumpleanos"). We decided to try and crowd source it, which worked ok: essentially we left the occasion empty, and if the person wanted to attach the gender-based possessive to it, they could. Otherwise, we would guess with what information we had. We figured, over time, we could actually create a service where we could sell that information (GaaS: Grammar as a service?). Turns out, people just wanted to be able to write their own titles, and we quickly trashed the idea in the early phases.