Being chill about everything can be a way of never admitting anything matters to you.

Indifference is cheap armour. If you never say you wanted it, you never have to be seen wanting it and missing, so being easy-going starts out as protection and slowly becomes a personality. The cost is that nobody can help you with something you have not admitted you care about, including you.

Pick one thing you have been pretending is no big deal and say the plain sentence to one person: you want this. Notice how exposed that feels and how little actually goes wrong. Caring out loud is a skill, and it gets easier with use.