Should I reach out to him on the anniversary of his fathers death?

I dated this guy last year we met in October and his father had passed away in May. He was still (Understandably) cut up about it but he was flakey with me, cancelled dates and didn’t show much interest so I stopped contacting him and I didn’t hear from him again.

Fast forward to April this year, I got drunk and sent him a message... nothing crazy but we started talking again. He came over to my place 2 weeks ago we didn’t have sex but let’s just say we ‘fooled around’. There’s not been much contact since then other than a few random texts so I gather that his interest level is still very low.

Next week will be the anniversary of his fathers death, should I let him know on the day that I am thinking of him/hope he’s ok... or just leave it?
Should I reach out to him on the anniversary of his fathers death?
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