That sucks. I don't think you can really feel too bad about the one guy. From what you have said, if he was struggling that much, the expat life wouldn't have been worked well for him either. It might have taken longer, but the result might have been the same. I know that doesn't really help though. I've had some friends who I noticed I haven't seen them post on Facebook lately, started doing some digging and it turns out they passed away. It's kind of a blow for sure. I had a friend similar to your first one that ended up passing away from cancer and it was really tragic. I feel so bad for her family. We weren't nearly as close as we had been in our younger years but it still leaves a hole.
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Yeah you are right about Ryan. he was very susceptible to substance abuse so not only would have the end result likely been the same but he also would have likely become a massive burden on me and anyone else that he met. Hindsight is 20/20 and all that and I like to think that there was something I could have done to change his mind but I was on the other side of the planet... there were people directly around him that were a lot more likely to be able to do something about it than I would have ever been able to.
It's tough for sure. Sadly, the older we get the more we are going to have to deal with it...