Do I bring it up?

So my boyfriend’s mom passed away fairly suddenly in the beginning of November of 2018. At the time he and I had only been together for about 3 months so it was a pretty difficult situation. That along with a close family member of mine passing away a few weeks prior, and me having my first major car accident a few weeks later. Anyways, things between us are great. We both feel very comfortable leaning on each other for emotional support when needed however, I’m kind of at a loss wondering whether or not I should ask him how he’s feeling— what with this being his first Mother’s Day without his mom. My boyfriend isn’t really one to go out of his way to talk about his feelings unless he feels ready to do so but that’s typically in regards to having a shitty day at work or getting into a disagreement with his dad etc etc. I kind of want to ask him how he’s feeling, just to make sure he’s doing okay, but I also don’t wanna push anything or make him feel sad by bringing it up in the first place. Part of me just wants to be straightforward (like I usually am with him) like hey I just wanted to make sure you were doing okay...something along the lines of help me figure out the best way to support you during this time, or, how would you like me to support you. Does that make any sense?? I don’t know, I feel like this is such a difficult situation, I don’t really have any friends that have experienced something like this so I don’t know where else to ask for advice. I love and care for him so much, I just want to make sure he’s okay. Thanks for reading.