It doesn't matter how long it has been. Sometimes you will see, hear or think something and it will bring you back to that grief like it is day 1 again. This will never change. Being a supportive friend or family member means accepting this, and being supportive of it.
For what it's worth: It's never too late to be whoever you want to be. I hope you live a life you're proud of, and if you find that you're not, I hope you have the strength to start over. -F. Scott Fitzgerald More