A little context:

My dad (59) is your typical blue pilled boomer. Mom and dad got divorced when I was 8 and my relationship with him has always been a bit awkward. I mean, sure we get along fine but it's as if we treat each other as guests. It's come to the point where we only speak to each other on Christmas and birthdays and every interaction is just awkward.

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His life has been a wreck and going downhill for the last 8 years. He lost his job and can't get a new one (presumably due to his age and lack of highschool diploma), had to move back with his mom and is pretty much broke living off my grandma's savings. He isn't very open about his problems with me (and me neither tbh) but from what my grandma tells me everytime I ask about him, I'd say he's been having a rough time for a while. It's not good for either him nor my grandma.

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It pains me to see my dad like this. He's always been a really nice guy and everybody that knows him, knows this. I'm starting to think he lost all hope and I want to help him turn his life around.

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Tomorrow is his birthday and I'll take him and my grandma to dinner. But I'd like to help him in the long run.

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Be honest askTRP. Is there any chance for a 59 year-old?