I was just thinking that I have no idea what to get my dad that he would actually like, when he emailed and said he'd prefer to just have a check.

I do really want him to be able to have something that he wants - my parents don't have a lot of money so almost never buy things for themselves. However, in the past he has had some issues spending money on destructive behaviors - gambling in particular - and I'm a bit worried that he's asking for money because he's gotten in trouble with this again (he said he wants a check to put money away in savings, but I doubt this is true). I don't want to enable unhealthy behaviors, and I'm somewhat worried that as it becomes more evident that we're now quite a bit better off economically than my parents that it will encourage this sort of behavior, with the thought that I can bail him out.

He doesn't shop online so an Amazon gift card, etc is out. Anyone have a similar experience? Thoughts on what to do?