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WWYD?
I have this "friend" who is always SUPER negative. (I can't avoid him/her, btw... it's not an option.) He/she is naturally a little pessimistic, but over the past year or so, has REALLY become a David/Debbie Downer due to additional stress.
WHEN is it okay to say something? (I wouldn't hesitate, btw, if this was a really good friend. I'd gently remind them of their blessings and try to help them focus on those while improving what they can where they can, etc.)
I know life can be tough. I know sometimes things are beyond your control. Trust me, I get it and have been there. But when someone constantly moans about how life sucks, I really want to snap back once in a while... life doesn't suck. Life can be tough, but at least it's life!! Situations might suck. Events suck. But life is a gift and to an extent, it's what you make of it... even in the crappy, hard times.
Re: WWYD?
I would maybe make a comment out of concern, just say it seems like you have been really stressed/upset of life in general lately. Is everything ok? Something to that degree. Maybe they don't realize they are doing this. It may be a reality check.
Ugh, it can be so frustrating to have a friend like that...I can think of one that is sort of a debbie downer but not too bad. I think I would show concern when she says negative things...maybe she'll take that opportunity to talk to you (if there is something serious she just needs to talk about) OR maybe she'll realize that she is just being a drama queen and things aren't that bad and could be much worse...