You can’t talk someone out of being in love with Darth Vader, and sadly, the worse it gets the more your friend might try to talk himself into trying to make it work because if there is a happy ending all the ways he’s had to abase himself to stay in the relationship will have been “worth it.
No matter what you say to someone whose parent or loved one died, it should be derivative of the same goal: communicating empathy and offering assistance, understanding what a person might need from you, and knowing how to phrase sentiments the right way.
This is what it looks like when you grieve the death of an estranged parent. It’s this surreal thing, where everyone expects you to feel something—yet you don’t. For me, it didn’t feel like I lost a parent, or a loved one, or even a close friend. It felt like I’d lost what could have been.