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First, I am very sorry for your loss.
Second, You can't live your life worrying how people will react to your actions. If you feel comfortable in asking Jason out so you can talk, then do it...but, I would make sure Jason is comfortable with it. Do you know how Jason feels about discussing his fiancee? Even though he's had two years to adjust/cope, he still may not want to talk about it.
As to the ring, I think it would be right for you to keep it. And, since you said you have a good relationship with his family, I don't see a reason why they would want you to give it up.
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AGD
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