We want to be there for those closest to us. Even though we may be ready to express our feelings, our loved ones might not be. There are people who, for varying reasons, might feel more familiar with "gritting their teeth and bearing it".
TL;DR
Starting the conversation can be as simple as asking them to hang out. Even if opening up doesn't feel comfortable for them, they can know that you're there and care. Don't push them. It is their decision of whether or not they appreciate the offered support.
Ways to start the conversation
Starting the conversation can be as simple as inviting them to coffee, getting outside, or ordering food delivery. Even if you’re long distance, the option for a virtual call, text or phone call still provides a way to open up conversation. The goal here is to create a comfortable environment to communicate within.
How to respond
One of the first things we can do to help ensure our loved one feels heard is to ask how they need us to show up. Asking them if they would like advice or feedback versus someone to simply listen allows them to let us know what their needs are in that moment.
When they choose to confide in us, it is important to use active listening skills. This is the practice of being present, and listening to understand, rather than to simply respond.
They haven't opened up
It's okay if they don't feel comfortable opening up yet. This is about letting them know we are there for them. If we let our ego get in the way, we end up making their feelings about us. This can unintentionally lead to putting a distance between ourselves and those we care about.
They are not going to open up
The important thing is to do all that we can do. We've heard the saying "you can lead a horse to water, but you can't make it drink". This is very true in that you are there to let them know they are cared about and supported, but ultimately, it is their decision of whether or not they accept it. What they feel is best for themselves may not be the same as what we think is best. What you can do is show up in the best way you know how, and to show up consistently. More times than not, knowing that someone is there for them does mean something to them.