Remember that people like being checked in on :) start small with a weekly check in, just ask how they're doing and if you can help. Try to remember that it feels good to be trusted and you can only feel as close as someone is close to you- so be close with them and lower your walls little by little.

If it makes it easier to face it, you don't have to use any special heartfelt message. I've done this before with my friends, and I normally just copy and paste the same message to all of them. I normally let them know that I hope they're doing well and ask if everything is going all right or if they have any exciting news.