Q: I really like this person and know they like me, too. I want to officially ask them out, but they are going through a tough time. I want to be there for them and wait to mention going out, but it’s kind of annoying and taking a little bit of a toll on me. They are a really amazing person who can’t see how much of a positive impact they make on the ones around them and how much they matter.

Okay, in a situation like this, I would recommend some kind of gesture to show how much they matter to everyone around them. Normally when a friend seems down and they’re just having a hard time, I would say that you just have to stick it through with them. But I feel like the situation is kind of different this time around. The feeling of like is mutual between you two, right? And the thing that’s stopping you guys from going out is this kind of mental slump the person has gotten into. But it’s not like this person is completely alone in the world, they have people (like you) who care about them deeply and whose lives are made better by their presence. You just have to help them see that. And I feel like the best way to do so is by creating/organizing a really sweet(maybe even romantic) surprise that will, not only help them to remember how much they matter, help your relationship get started. I know that you just want to be there with them and wait as long as it takes, but you’re human too. And tough situations like these where your relationship is at a standstill and you feel helpless to do anything, can’t help but take a toll on you. So I feel like if you show up to school with a really thoughtful present, and it doesn’t have to be anything complicated, it could really just be a box of cookies and a meaningful note, it’ll really end up helping both of you get back on track.