I think you've really got something there! And now for the criticism :-) "real advice from real people" sounds a bit too much like hard-hitting investigative r

I think you've really got something there! And now for the criticism :-) "real advice from real people" sounds a bit too much like hard-hitting investigative reporting to me. How about "Should I break up with him?". If it resonates directly with someone, that counts for a lot more than mathematically covering the domain. I like the idea of using the exact language of the target audience, concrete and specific - use a popular idiom if there is one (it doesn't matter if it doesn't match people outside the target). For this reason, I think separating boys and girls makes sense, because you can say "him" or "her" instead of being forced to abstract generalities. Make it concrete and "relateable". I think also that people don't actually want "advice", they just want to be listened to, get it off their chest. I get the vibe from the site that it has a gossip quality... almost like two people discussing the problems of a third-party. I don't know if that's something you want to cultivate, or if it would help the site or not - just mentioning it as an observation. You're sure to have a problem with trolls sooner or later, causing grief amongst those in an emotional state. Possibly, a very clear message and an effective way for users to deal with it is more important than preventing it 100%. Making it seem like third-party ("my friend has this problem...") could add a distance, that makes it easier for people to speak freely.