How to reach out many months later

I lost someone around a year ago and my friend lost someone almost 6 months after. I remember having a really hard time for a while personally after 6 months. We spoke a bit about his experience but he didn't seem like he wanted to. However, in my experience I wanted to speak about grief with people after some time, and now that it has been a while for my friend I think I want to mention it without it feeling forced and was wondering if anyone knew how. I wish I could find a nice post to send his way, something low pressure but I'm struggling to find anything and just want to be open to him if he wants to talk.

At the same time in my personal experience it was very difficult for me when people walked on eggshells around me and I don't want to do that with him.

Thoughts? Ideas?