How about sending an image as opposed to text?



A funny pic or GIF, or meme he might enjoy, or an inspirational / motivational one, since he's going through some rough times.


I sometimes send my bf those when he's severely depressed, and silent. Its a good way to let him know I'm thinking about him, without any pressure to respond.


For you it could be that, and a way of keeping communication lines open without seeming clingy or pushy.