It'll be fine

I try to be funny (only im bad at being funny lmao most of the stuff i say is lame anyway XD) they usually just end up laughing at how lame i am...either that or i try to make them see the good rather than the bad if that makes sense

That's a really difficult question. It depends on the person, the reason why you're trying to sheer them up, your relationship with them, how much you know about the issue... etc There isn't a sure way to go about it. My piece is that it's important to not just pity a suffering person. Show them support, while still making sure to remind them that life continues and eventually they'll need to get over it.

A good thing is to remind them they are not alone in their plights. Another good thing is to remind them of their qualities that will carry them forward. Most of this type of thing is about relevance and relation like Key said. Some people do not want to feel patronized and some are not comfortable accepting help from others easily so it's delicate for sure. +1 hunter listening is a big one.

You have a point, DarkuSchneider. Sometimes a person's ego would prevent them from accepting help because they do not want to appear to be weak to their friends or family. That could be detrimental to them because sometimes you don't always have the strength to deal with a problem by yourself.

Exactly, you could end up making them feel worse if their inner strength is a core part of their character. But even Erza's stubborn ass has to pressed a little if they are too far in the funk too long. Always a delicate thing, just have to do your best to read them.