Ooh very good and tough question, I'll say probably #2 because it's no big deal to never have something that's probably impossible or at least difficult to obtain, loosing something forever we probably already experienced this therefore you're already vulnerable so generally its usually the worst of the two.
As I get closer to death, be it natural or CTB, all of the things I will never experience are coming into focus and the pain I feel around that is very similar to a sense of loss, it is enormously overwhelming.
For me, it's a mixture of the two. I wanted something I never had, only to realize I could have had it but lost the opportunity and destroyed my life forever.
It's really hard to choose between the two as I feel equally bad with both choices. However, if I choose, in general, I'd go with #2, having something I once enjoyed and then losing it forever.
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